(E)-2-benzoyl-3-cyclohexylacrylonitrile | 1261378-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-benzoyl-3-cyclohexylacrylonitrile
• CAS: 1261378-73-7
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: INOJXJFDGKMBQI-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-benzoyl-3-cyclohexylacrylonitrile 在 叔丁基过氧化氢 、 S-Α,Α-双(3,5-二甲基苯基)脯氨醇 作用下， 以 癸烷 、 间二甲苯 为溶剂， 以95%的产率得到(2R,3S)-2-benzoyl-3-cyclohexyloxirane-2-carbonitrile
  参考文献：
  名称：

  Organocatalytic Stereoselective Epoxidation of Trisubstituted Acrylonitriles

  摘要：

  The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the transisomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).

  DOI：

  10.1021/jo102020a

文献信息

• DABCO-Mediated [4 + 4]-Domino Annulation: Access to Functionalized Eight-Membered Cyclic Ethers
  作者：Ling Liang、Erqing Li、Xuelin Dong、You Huang

  DOI：10.1021/acs.orglett.5b02498

  日期：2015.10.2

  DABCO-mediated [4 + 4] domino annulation reactions of ynones and α-cyano-α,β-unsaturated ketones were discovered. The domino process affords an alternative route to eight-membered cyclic ethers in good yields under mild conditions.

  发现了DABCO介导的[4 + 4]炔酮和α-氰基-α，β-不饱和酮的多米诺环化反应。在温和的条件下，多米诺骨牌工艺提供了一种以高收率获得八元环醚的替代途径。
• Organocatalytic asymmetric synthesis of highly substituted pyrrolidines bearing a stereogenic quaternary centre at the 3-position
  作者：Soumendranath Mukhopadhyay、Subhas Chandra Pan

  DOI：10.1039/c8ob02648c

  日期：——

  An organocatalytic asymmetric cascade reaction has been developed for the synthesis of highly substituted pyrrolidines having a stereogenic quaternary centre at the 3-position. N-Tosyl aminomethyl enone and trans-α-cyano-α,β-unsaturated ketone were utilized as the reaction partners in this method. Cinchonidine derived bifunctional amino-squaramide catalysts were the best to obtain the products in high

  已经开发了有机催化不对称级联反应，用于合成在3-位具有立体异构的季中心的高度取代的吡咯烷。该方法以N-甲苯磺酰基氨基甲基烯酮和反式-α-氰基-α，β-不饱和酮为反应伙伴。辛可尼定衍生的双官能氨基-方酸酰胺催化剂是获得高对映体和非对映体选择性的最佳产品。
• Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter via Double Michael Reaction Involving Dynamic Kinetic Resolution
  作者：Sara Meninno、Gianluca Croce、Alessandra Lattanzi

  DOI：10.1021/ol4014975

  日期：2013.7.5

  The stereoselective synthesis of highly functionalized tetrahydrothiophenes bearing three contiguous stereocenters, one of them quaternary, can be achieved by reacting trans-α-cyano-α,β-unsaturated ketones and trans-tert-butyl 4-mercapto-2-butenoate in the presence of a readily available amine thiourea. The products are obtained in high yield, good diastereoselectivity, and excellent enantioselectivity

  可以通过在存在下使反式-α-氰基-α，β-不饱和酮与反式-叔丁基4-巯基-2-丁烯酸酯反应，来实现带有三个连续的立体中心的高官能化四氢噻吩的立体选择性合成。一种现成的胺硫脲。以高收率，良好的非对映选择性和优异的对映选择性获得产物。四氢噻吩的整体形成是通过级联双迈克尔反应进行的，该反应涉及动态动力学拆分的高效过程。
• Chiral Aminomethylbinaphthol‐Catalyzed Diastereo‐ and Enantioselective Epoxidation of Trisubstituted Acrylonitriles
  作者：Eri Ogino、Satoru Kuwano、Takayoshi Arai

  DOI：10.1002/adsc.202200036

  日期：2022.4.12

  3′-bisaminomethyl-binaphthol (AMB) is an organocatalyst for the asymmetric epoxidation of trisubstituted acrylonitriles. Using cumene hydroperoxide (CHP) as an oxidant, 3,3′-bis((R,R)-2-phenylethylaminomethyl)-(R)-binaphthol (AMB2) catalyzed epoxidation of trans-2-aroyl-3-arylacrylonitriles at −30 °C to give the chiral epoxides as a single diastereomer with enantioselective manner ranging from 15% ee to 97%

  手性C 2 -对称 3,3'-二氨基甲基-联萘酚 ( AMB ) 是一种用于三取代丙烯腈不对称环氧化的有机催化剂。使用氢过氧化枯烯 (CHP) 作为氧化剂，3,3'-双(( R , R )-2-苯乙基氨基甲基)-( R )-联萘酚( AMB2 )在 - 30 °C 得到手性环氧化物作为单一非对映异构体，对映选择性范围为 15% ee 至 97% ee。