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环丙基甲醛：修订间差异

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小 清理跨語言連結丁二酸二乙酯成為內部連結:編輯摘要的紅色內部連結乃正常現象，經繁簡轉換後存在，非bot錯誤編輯 (本次機械人作業已完成83.6%)
 
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环丙基甲醛可由[[9-硼二环［3.3.1］壬烷|9-硼杂双环[3.3.1]壬烷]]<ref>{{cite journal | last=Cha | first=Jin Soon | last2=Kim | first2=Jin Euog | last3=Oh | first3=Se Yeon | last4=Kim | first4=Jong Dae | title=One-pot conversion of carboxylic acids to aldehydes through treatment of acyloxy-9-borabicyclo[3.3.1]nonanes with lithium 9-boratabicyclo[3.3.1]nonane | url=https://archive.org/details/sim_tetrahedron-letters_1987_28_39/page/4575 | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=28 | issue=39 | year=1987 | issn=0040-4039 | doi=10.1016/s0040-4039(00)96568-7 | pages=4575–4578 | language = en}}</ref>、二(二乙氨基)氢化铝<ref>{{cite journal | last=CHA | first=J. S. | last2=LEE | first2=K. D. | last3=KWON | first3=O. O. | last4=KIM | first4=J. M. | last5=LEE | first5=H. S. | title=ChemInform Abstract: Systematic Study on Bis(dialkylamino)aluminum Hydride: Reexamination of the Reagents for Reduction of Carboxylic Acids to Aldehydes. | journal=ChemInform | publisher=Wiley | volume=26 | issue=51 | date=2010-08-16 | issn=0931-7597 | doi=10.1002/chin.199551071 | language = en}}</ref>、1,1,2-三甲基丙基溴代甲硼烷二甲基硫醚配合物<ref>{{cite journal | last=Cha | first=Jin Soon | last2=Kim | first2=Jin Euog | last3=Oh | first3=Se Yeon | last4=Lee | first4=Jae Cheol | last5=Lee | first5=Kwang Woo | title=Direct conversion of saturated and unsaturated carboxylic acids into aldehydes by thexylbromoborane-dimethyl sulfide | url=https://archive.org/details/sim_tetrahedron-letters_1987_28_21/page/2389 | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=28 | issue=21 | year=1987 | issn=0040-4039 | doi=10.1016/s0040-4039(00)96132-x | pages=2389–2392 | language = en}}</ref>等还原剂还原[[环丙基甲酸]]制得。[[高碘酸]]<ref>{{cite journal | last=Ganesamoorthy | first=S. | last2=Shanmugasundaram | first2=K. | last3=Karvembu | first3=R. | title=Mild oxidation of alcohols with periodic acid catalyzed by [Ru(acac)2(CH3CN)2]PF6 in water | journal=Catalysis Communications | publisher=Elsevier BV | volume=10 | issue=14 | year=2009 | issn=1566-7367 | doi=10.1016/j.catcom.2009.06.010 | pages=1835–1838 | language = en}}</ref>、[[重铬酸钠]]<ref>{{cite journal | last=Lou | first=Ji-Dong | last2=Gao | first2=Chun-Ling | last3=Ma | first3=Yi-Chun | last4=Huang | first4=Li-Hong | last5=Li | first5=Li | title=Shaken not stirred; oxidation of alcohols with sodium dichromate | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=47 | issue=3 | year=2006 | issn=0040-4039 | doi=10.1016/j.tetlet.2005.11.024 | pages=311–313 | language=en}}</ref>、3-亚碘酰苯甲酸<ref>{{cite journal | last=Yusubov | first=Mekhman S. | last2=Gilmkhanova | first2=Marina P. | last3=Zhdankin | first3=Viktor V. | last4=Kirschning | first4=Andreas | title=m-Iodosylbenzoic Acid as a Convenient Recyclable Reagent for Highly Efficient RuCl3-Catalyzed Oxidation of Alcohols to Carbonyl Compounds. | journal=ChemInform | publisher=Wiley | volume=38 | issue=28 | date=2007-07-10 | issn=0931-7597 | doi=10.1002/chin.200728043 | language=en}}</ref>、[[硝酸铈铵]]<ref>{{cite journal | last=Young | first=Lewis Brewster | last2=Trahanovsky | first2=Walter S. | title=Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol | journal=The Journal of Organic Chemistry | publisher=American Chemical Society (ACS) | volume=32 | issue=7 | year=1967 | issn=0022-3263 | doi=10.1021/jo01282a058 | pages=2349–2350 | language = en}}</ref>、[[氧气]]<ref>{{cite journal | last=Wang | first=Xinliang | last2=Liu | first2=Renhua | last3=Jin | first3=Yu | last4=Liang | first4=Xinmiao | title=TEMPO/HCl/NaNO2 Catalyst: A Transition-Metal-Free Approach to Efficient Aerobic Oxidation of Alcohols to Aldehydes and Ketones Under Mild Conditions | journal=Chemistry - A European Journal | publisher=Wiley | volume=14 | issue=9 | date=2008-03-17 | issn=0947-6539 | doi=10.1002/chem.200701818 | pages=2679–2685 | language=en}}</ref>等氧化剂氧化[[环丙基甲醇]]也能得到环丙基甲醛。
环丙基甲醛可由[[9-硼二环［3.3.1］壬烷|9-硼杂双环[3.3.1]壬烷]]<ref>{{cite journal | last=Cha | first=Jin Soon | last2=Kim | first2=Jin Euog | last3=Oh | first3=Se Yeon | last4=Kim | first4=Jong Dae | title=One-pot conversion of carboxylic acids to aldehydes through treatment of acyloxy-9-borabicyclo[3.3.1]nonanes with lithium 9-boratabicyclo[3.3.1]nonane | url=https://archive.org/details/sim_tetrahedron-letters_1987_28_39/page/4575 | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=28 | issue=39 | year=1987 | issn=0040-4039 | doi=10.1016/s0040-4039(00)96568-7 | pages=4575–4578 | language = en}}</ref>、二(二乙氨基)氢化铝<ref>{{cite journal | last=CHA | first=J. S. | last2=LEE | first2=K. D. | last3=KWON | first3=O. O. | last4=KIM | first4=J. M. | last5=LEE | first5=H. S. | title=ChemInform Abstract: Systematic Study on Bis(dialkylamino)aluminum Hydride: Reexamination of the Reagents for Reduction of Carboxylic Acids to Aldehydes. | journal=ChemInform | publisher=Wiley | volume=26 | issue=51 | date=2010-08-16 | issn=0931-7597 | doi=10.1002/chin.199551071 | language = en}}</ref>、1,1,2-三甲基丙基溴代甲硼烷二甲基硫醚配合物<ref>{{cite journal | last=Cha | first=Jin Soon | last2=Kim | first2=Jin Euog | last3=Oh | first3=Se Yeon | last4=Lee | first4=Jae Cheol | last5=Lee | first5=Kwang Woo | title=Direct conversion of saturated and unsaturated carboxylic acids into aldehydes by thexylbromoborane-dimethyl sulfide | url=https://archive.org/details/sim_tetrahedron-letters_1987_28_21/page/2389 | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=28 | issue=21 | year=1987 | issn=0040-4039 | doi=10.1016/s0040-4039(00)96132-x | pages=2389–2392 | language = en}}</ref>等还原剂还原[[环丙基甲酸]]制得。[[高碘酸]]<ref>{{cite journal | last=Ganesamoorthy | first=S. | last2=Shanmugasundaram | first2=K. | last3=Karvembu | first3=R. | title=Mild oxidation of alcohols with periodic acid catalyzed by [Ru(acac)2(CH3CN)2]PF6 in water | journal=Catalysis Communications | publisher=Elsevier BV | volume=10 | issue=14 | year=2009 | issn=1566-7367 | doi=10.1016/j.catcom.2009.06.010 | pages=1835–1838 | language = en}}</ref>、[[重铬酸钠]]<ref>{{cite journal | last=Lou | first=Ji-Dong | last2=Gao | first2=Chun-Ling | last3=Ma | first3=Yi-Chun | last4=Huang | first4=Li-Hong | last5=Li | first5=Li | title=Shaken not stirred; oxidation of alcohols with sodium dichromate | journal=Tetrahedron Letters | publisher=Elsevier BV | volume=47 | issue=3 | year=2006 | issn=0040-4039 | doi=10.1016/j.tetlet.2005.11.024 | pages=311–313 | language=en}}</ref>、3-亚碘酰苯甲酸<ref>{{cite journal | last=Yusubov | first=Mekhman S. | last2=Gilmkhanova | first2=Marina P. | last3=Zhdankin | first3=Viktor V. | last4=Kirschning | first4=Andreas | title=m-Iodosylbenzoic Acid as a Convenient Recyclable Reagent for Highly Efficient RuCl3-Catalyzed Oxidation of Alcohols to Carbonyl Compounds. | journal=ChemInform | publisher=Wiley | volume=38 | issue=28 | date=2007-07-10 | issn=0931-7597 | doi=10.1002/chin.200728043 | language=en}}</ref>、[[硝酸铈铵]]<ref>{{cite journal | last=Young | first=Lewis Brewster | last2=Trahanovsky | first2=Walter S. | title=Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol | journal=The Journal of Organic Chemistry | publisher=American Chemical Society (ACS) | volume=32 | issue=7 | year=1967 | issn=0022-3263 | doi=10.1021/jo01282a058 | pages=2349–2350 | language = en}}</ref>、[[氧气]]<ref>{{cite journal | last=Wang | first=Xinliang | last2=Liu | first2=Renhua | last3=Jin | first3=Yu | last4=Liang | first4=Xinmiao | title=TEMPO/HCl/NaNO2 Catalyst: A Transition-Metal-Free Approach to Efficient Aerobic Oxidation of Alcohols to Aldehydes and Ketones Under Mild Conditions | journal=Chemistry - A European Journal | publisher=Wiley | volume=14 | issue=9 | date=2008-03-17 | issn=0947-6539 | doi=10.1002/chem.200701818 | pages=2679–2685 | language=en}}</ref>等氧化剂氧化[[环丙基甲醇]]也能得到环丙基甲醛。


{{link-de|丁二酸二乙酯|Bernsteinsäurediethylester}}的[[酮醇缩合]]反应可以得到[[:d:Q82358592|2-羟基环丁酮]]<ref>{{cite journal | last=Gatling | first=Sterling C. | last2=Jackson | first2=James E. | title=Reactivity Control via Dihydrogen Bonding: Diastereoselection in Borohydride Reductions of α-Hydroxyketones | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=121 | issue=37 | year=1999 | issn=0002-7863 | doi=10.1021/ja991784n | pages=8655–8656 | language=en}}</ref>，它可以被[[氢化铝锂]]还原为1,2-环丁二醇，再在三氟化硼二丁醚缩环，可以得到环丙基甲醛：<ref>{{cite journal | title= Cyclopropanecarboxaldehyde| journal=Organic Syntheses | publisher=Organic Syntheses | volume=60 | year=1981 | issn=0078-6209 | doi=10.15227/orgsyn.060.0025 | language = en | page=25}}</ref>
[[丁二酸二乙酯]]的[[酮醇缩合]]反应可以得到[[:d:Q82358592|2-羟基环丁酮]]<ref>{{cite journal | last=Gatling | first=Sterling C. | last2=Jackson | first2=James E. | title=Reactivity Control via Dihydrogen Bonding: Diastereoselection in Borohydride Reductions of α-Hydroxyketones | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=121 | issue=37 | year=1999 | issn=0002-7863 | doi=10.1021/ja991784n | pages=8655–8656 | language=en}}</ref>，它可以被[[氢化铝锂]]还原为1,2-环丁二醇，再在三氟化硼二丁醚缩环，可以得到环丙基甲醛：<ref>{{cite journal | title= Cyclopropanecarboxaldehyde| journal=Organic Syntheses | publisher=Organic Syntheses | volume=60 | year=1981 | issn=0078-6209 | doi=10.15227/orgsyn.060.0025 | language = en | page=25}}</ref>
: [[File:CPCA_aus_2-Hydroxycyclobutanon.svg|415px]]
: [[File:CPCA_aus_2-Hydroxycyclobutanon.svg|415px]]
[[2,3-二氢呋喃]]在加热、加压下经[[氧化铝]]催化下发生[[重排反应]]，也能得到环丙基甲醛，副产物是{{link-de|反式巴豆醛|Trans-Crotonaldehyd|反式}}[[巴豆醛]]：<ref>{{cite web|authors=Liang, Shaowo; Price, Timothy W|title=Process for the conversion of 2,3-dihydrofuran to cyclopropanecarboxaldehyde|publisher=US5633410A|url=https://worldwide.espacenet.com/patent/search/family/024836438/publication/US5633410A?q=pn%3DUS5633410|language=en|accessdate=2021-08-29|date=1997-05-27|archive-date=2021-08-29|archive-url=https://web.archive.org/web/20210829100251/https://worldwide.espacenet.com/patent/search/family/024836438/publication/US5633410A?q=pn%3DUS5633410|dead-url=no}}</ref>
[[2,3-二氢呋喃]]在加热、加压下经[[氧化铝]]催化下发生[[重排反应]]，也能得到环丙基甲醛，副产物是{{link-de|反式巴豆醛|Trans-Crotonaldehyd|反式}}[[巴豆醛]]：<ref>{{cite web|authors=Liang, Shaowo; Price, Timothy W|title=Process for the conversion of 2,3-dihydrofuran to cyclopropanecarboxaldehyde|publisher=US5633410A|url=https://worldwide.espacenet.com/patent/search/family/024836438/publication/US5633410A?q=pn%3DUS5633410|language=en|accessdate=2021-08-29|date=1997-05-27|archive-date=2021-08-29|archive-url=https://web.archive.org/web/20210829100251/https://worldwide.espacenet.com/patent/search/family/024836438/publication/US5633410A?q=pn%3DUS5633410|dead-url=no}}</ref>

2023年1月7日 (六) 19:42的最新版本

环丙基甲醛
IUPAC名
cyclopropanecarbaldehyde
英文名 Cyclopropanecarboxaldehyde
别名 环丙甲醛
甲酰基环丙烷
识别
CAS号 1489-69-6  checkY
PubChem 123114
SMILES
 
  • C1CC1C=O
InChI
 
  • 1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2
InChIKey JMYVMOUINOAAPA-UHFFFAOYSA-N
性质
化学式 C4H6O
摩尔质量 70.09 g·mol−1
外观 无色液体
密度 0.938 g·cm−3[1]
沸点 98—101 °C（371—374 K）[2]
溶解性（水） 可溶
危险性
GHS提示词 危险
H-术语 H225, H314
P-术语 P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310
相关物质
相关化学品 环丁基甲醛
环戊基甲醛
环己基甲醛
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

环丙基甲醛是一种有机化合物，化学式为C4H6O，是环丙烷的一个氢被甲酰基取代的产物。它是无色至黄色的液体，可溶于水及一些有机溶剂。

合成

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环丙基甲醛可由9-硼杂双环[3.3.1]壬烷[3]、二(二乙氨基)氢化铝[4]、1,1,2-三甲基丙基溴代甲硼烷二甲基硫醚配合物[5]等还原剂还原环丙基甲酸制得。高碘酸[6]、重铬酸钠[7]、3-亚碘酰苯甲酸[8]、硝酸铈铵[9]、氧气[10]等氧化剂氧化环丙基甲醇也能得到环丙基甲醛。

丁二酸二乙酯的酮醇缩合反应可以得到2-羟基环丁酮[11]，它可以被氢化铝锂还原为1,2-环丁二醇，再在三氟化硼二丁醚缩环，可以得到环丙基甲醛：[12]

2,3-二氢呋喃在加热、加压下经氧化铝催化下发生重排反应，也能得到环丙基甲醛，副产物是反式（德语：Trans-Crotonaldehyd）巴豆醛：[13]

反应

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环丙基甲醛可以发生醛的特征反应，如加氢还原为环丙基甲醇[14]或氧化为环丙基甲酸[15]；它和苄胺在对甲苯磺酸的催化下缩合，得到N-(环丙基亚甲基)苄胺[16]，在该体系中，加入二硼酸可以将亚胺加氢为胺[17]；和氰乙酸乙酯发生Knoevenagel缩合反应，生成2-氰基-3-环丙基-2-丙烯酸乙酯。[18]在三氟化硼乙醚的存在下，它和2-叠氮基乙醇于二氯甲烷中反应，可以得到2-环丙基-4,5-二氢噁唑。[19]

它和二环戊基锌反应，可以得到α-环丙基环戊基甲醇。[20]

应用

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环丙基甲醛和正丙胺缩合后氢化，得到N-(环丙基甲基)丙胺，它再与4-氯-3,5-二硝基三氟甲苯反应，可以得到除草剂环丙氟灵（德语：Profluralin）：[21]

以环丙基甲醛为原料可以合成环丙基乙炔。它首先和三氯乙酸反应，得到α-三氯甲基环丙基甲醇，经对甲基苯基磺酰氯（TsCl）转化为对甲苯磺酸酯，所得的酯再与甲基锂反应，水解后生成环丙基乙炔。[22]

参考文献

[编辑]
  1. ^ Haynes, William. CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. Boca Raton, Florida: CRC Press. 2017: 3-138. ISBN 978-1-4987-5429-3. OCLC 957751024 （英语）. 
  2. ^ Venus-Danilova, E. D.; Kazimirova, V. F. Aldehydes and hydroxyaldehydes of the polymethylene series. IX. Isomeric changes of cyclopropylformaldehyde. Zhurnal Obshchei Khimii. 1938, 8: 1438-1436. ISSN 0044-460X （俄语）. 
  3. ^ Cha, Jin Soon; Kim, Jin Euog; Oh, Se Yeon; Kim, Jong Dae. One-pot conversion of carboxylic acids to aldehydes through treatment of acyloxy-9-borabicyclo[3.3.1]nonanes with lithium 9-boratabicyclo[3.3.1]nonane. Tetrahedron Letters (Elsevier BV). 1987, 28 (39): 4575–4578. ISSN 0040-4039. doi:10.1016/s0040-4039(00)96568-7 （英语）. 
  4. ^ CHA, J. S.; LEE, K. D.; KWON, O. O.; KIM, J. M.; LEE, H. S. ChemInform Abstract: Systematic Study on Bis(dialkylamino)aluminum Hydride: Reexamination of the Reagents for Reduction of Carboxylic Acids to Aldehydes.. ChemInform (Wiley). 2010-08-16, 26 (51). ISSN 0931-7597. doi:10.1002/chin.199551071 （英语）. 
  5. ^ Cha, Jin Soon; Kim, Jin Euog; Oh, Se Yeon; Lee, Jae Cheol; Lee, Kwang Woo. Direct conversion of saturated and unsaturated carboxylic acids into aldehydes by thexylbromoborane-dimethyl sulfide. Tetrahedron Letters (Elsevier BV). 1987, 28 (21): 2389–2392. ISSN 0040-4039. doi:10.1016/s0040-4039(00)96132-x （英语）. 
  6. ^ Ganesamoorthy, S.; Shanmugasundaram, K.; Karvembu, R. Mild oxidation of alcohols with periodic acid catalyzed by [Ru(acac)2(CH3CN)2]PF6 in water. Catalysis Communications (Elsevier BV). 2009, 10 (14): 1835–1838. ISSN 1566-7367. doi:10.1016/j.catcom.2009.06.010 （英语）. 
  7. ^ Lou, Ji-Dong; Gao, Chun-Ling; Ma, Yi-Chun; Huang, Li-Hong; Li, Li. Shaken not stirred; oxidation of alcohols with sodium dichromate. Tetrahedron Letters (Elsevier BV). 2006, 47 (3): 311–313. ISSN 0040-4039. doi:10.1016/j.tetlet.2005.11.024 （英语）. 
  8. ^ Yusubov, Mekhman S.; Gilmkhanova, Marina P.; Zhdankin, Viktor V.; Kirschning, Andreas. m-Iodosylbenzoic Acid as a Convenient Recyclable Reagent for Highly Efficient RuCl3-Catalyzed Oxidation of Alcohols to Carbonyl Compounds.. ChemInform (Wiley). 2007-07-10, 38 (28). ISSN 0931-7597. doi:10.1002/chin.200728043 （英语）. 
  9. ^ Young, Lewis Brewster; Trahanovsky, Walter S. Cerium(IV) oxidation of organic compounds. III. Preparation of cyclopropanecarboxaldehyde from cyclopropanemethanol. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1967, 32 (7): 2349–2350. ISSN 0022-3263. doi:10.1021/jo01282a058 （英语）. 
  10. ^ Wang, Xinliang; Liu, Renhua; Jin, Yu; Liang, Xinmiao. TEMPO/HCl/NaNO2 Catalyst: A Transition-Metal-Free Approach to Efficient Aerobic Oxidation of Alcohols to Aldehydes and Ketones Under Mild Conditions. Chemistry - A European Journal (Wiley). 2008-03-17, 14 (9): 2679–2685. ISSN 0947-6539. doi:10.1002/chem.200701818 （英语）. 
  11. ^ Gatling, Sterling C.; Jackson, James E. Reactivity Control via Dihydrogen Bonding: Diastereoselection in Borohydride Reductions of α-Hydroxyketones. Journal of the American Chemical Society (American Chemical Society (ACS)). 1999, 121 (37): 8655–8656. ISSN 0002-7863. doi:10.1021/ja991784n （英语）. 
  12. ^ Cyclopropanecarboxaldehyde. Organic Syntheses (Organic Syntheses). 1981, 60: 25. ISSN 0078-6209. doi:10.15227/orgsyn.060.0025 （英语）. 
  13. ^ Liang, Shaowo; Price, Timothy W. Process for the conversion of 2,3-dihydrofuran to cyclopropanecarboxaldehyde. US5633410A. 1997-05-27 [2021-08-29]. （原始内容存档于2021-08-29） （英语）. 
  14. ^ Kleemiss, Wolfgang; Feld, Marcel. Hydrogenation process and catalysts for the preparation of (hydroxymethyl)cyclopropane from formylcyclopropane. EP 794166 A2. 1997 （德语）. 
  15. ^ Zhao, Junfeng; Mück-Lichtenfeld, Christian; Studer, Armido. Cooperative N-Heterocyclic Carbene (NHC) and Ruthenium Redox Catalysis: Oxidative Esterification of Aldehydes with Air as the Terminal Oxidant. Advanced Synthesis & Catalysis (Wiley). 2013-04-08, 355 (6): 1098–1106. ISSN 1615-4150. doi:10.1002/adsc.201300034 （英语）. 
  16. ^ Huang, Huawen; Ji, Xiaochen; Wu, Wanqing; Jiang, Huanfeng. A cascade approach to fused indolizinones through Lewis acid–copper(i) relay catalysis. Chemical Communications (Royal Society of Chemistry (RSC)). 2013, 49 (32): 3351. ISSN 1359-7345. doi:10.1039/c3cc40643a （英语）. 
  17. ^ Wei, Yahui; Zhao, Cong; Xuan, Qingqing; Song, Qiuling. An expedient and novel strategy for reductive amination by employing H2O as both a hydrogen source and solventviaB2(OH)4/H2O systems. Organic Chemistry Frontiers (Royal Society of Chemistry (RSC)). 2017, 4 (12): 2291–2295. ISSN 2052-4129. doi:10.1039/c7qo00769h （英语）. 
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