(E)-2-Benzoyl-3-o-tolyl-acrylonitrile | 103457-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2-Benzoyl-3-o-tolyl-acrylonitrile
• 英文别名: (E)-2-benzoyl-3-(2-methylphenyl)prop-2-enenitrile
• CAS: 103457-29-0
• 化学式: C₁₇H₁₃NO
• 分子量: 247.296
• InChiKey: YZOHIUPWKOHKGU-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-Benzoyl-3-o-tolyl-acrylonitrile 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77%的产率得到(2R,3S)-2-benzoyl-3-(o-tolyl)oxirane-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

• One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines
  作者：Sara Meninno、Amedeo Capobianco、Andrea Peluso、Alessandra Lattanzi

  DOI：10.1039/c4gc02191f

  日期：——

  An effective one-pot sequential Michael addition/deprotection/cyclization/tautomerization approach to N-unprotected fully substituted trans-2-pyrrolines has been developed.

  已开发出一种有效的一锅顺序Michael加成/去保护/环化/互变异构化方法，用于合成未保护的全取代的trans-2-吡咯烯。
• 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。
• Organocatalytic Asymmetric Synthesis of Pentasubstituted Tetrahydrothiopyrans Bearing a Quaternary Centre through a Double Michael Reaction
  作者：Subhas Pan、Buddhadeb Mondal

  DOI：10.1055/s-0036-1591736

  日期：2018.3

  An organocatalytic, asymmetric, double-Michael strategy has been developed employing trans-α-cyano-α,β-unsaturated ketones for the synthesis of pentasubstituted tetrahydrothiopyrans bearing a quaternary center. A proline-derived bifunctional thiourea was found to be the most effective catalyst for this reaction. With 10 mol% of catalyst, good yields and good to high diastereomeric ratios, as well as

  使用反式-α-氰基-α,β-不饱和酮开发了一种有机催化、不对称、双迈克尔策略，用于合成带有四元中心的五取代四氢噻喃。脯氨酸衍生的双功能硫脲被发现是该反应最有效的催化剂。使用 10 mol% 的催化剂，在温和的反应条件下，使用各种四氢噻喃可以获得良好的产率和良好的非对映体比例以及出色的对映选择性。
• Phosphine-catalyzed [3 + 2] annulation of β-sulfonamido-substituted enones with <i>trans</i>-α-cyano-α,β-unsaturated ketones for the synthesis of highly substituted pyrrolidines
  作者：Zhenzhen Gao、Lei Xie、Lusha Ji、Xin Ma、Xiaojing Li、Honglei Liu、Hongchao Guo

  DOI：10.1039/d1ra07881j

  日期：——

  To synthesize highly substituted pyrrolidines, we developed a phosphine-catalyzed [3 + 2] annulation of β-sulfonamido-substituted enones with trans-α-cyano-α,β-unsaturated ketones. We prepared a series of pyrrolidines under mild conditions with high yields and moderate-to-good diastereoselectivities. A catalytic mechanism for this reaction is suggested.

  为了合成高度取代的吡咯烷，我们开发了一种膦催化的 [3 + 2] β-磺酰胺基取代的烯酮与反式-α-氰基-α,β-不饱和酮的环化反应。我们在温和条件下制备了一系列具有高产率和中等至良好非对映选择性的吡咯烷。提出了该反应的催化机制。