1,2-di(2-benzoyl-1-phenylvinylamino)ethane | 10441-73-3

• 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: 1,2-di(2-benzoyl-1-phenylvinylamino)ethane
• 英文别名: 3-[2-[(3-oxo-1,3-diphenylprop-1-enyl)amino]ethylamino]-1,3-diphenylprop-2-en-1-one
• CAS: 10441-73-3
• 化学式: C₃₂H₂₈N₂O₂
• 分子量: 472.587
• InChiKey: NZNNIFBHJPDQOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙二胺 、 二苯基丙炔酮 在 gallium(III) triflate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以47%的产率得到1,2-di(2-benzoyl-1-phenylvinylamino)ethane
  参考文献：
  名称：

  Recyclable gallium(III) triflate-catalyzed [4+3] cycloaddition for synthesis of 2,4-disubstituted-3H-benzo[b][1,4]diazepines

  摘要：

  Simple and efficient Ga(OTf)(3)-catalyzed [4+3] cycloaddition of 1,3-diarylpropynones and o-phenylenediamines is developed for the preparation of 2,4-disubstituted-3H-benzo[b][1,4]diazepines. The reaction has advantages of using a green solvent, generating a minimal amount of waste, and easy catalyst recycle. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.092

文献信息

• Dissecting Alkynes: Full Cleavage of Polarized C≡C Moiety via Sequential Bis-Michael Addition/Retro-Mannich Cascade
  作者：Saumya Roy、Maria P. Davydova、Runa Pal、Kerry Gilmore、Genrikh A. Tolstikov、Sergei F. Vasilevsky、Igor V. Alabugin

  DOI：10.1021/jo201259j

  日期：2011.9.16

  The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to e full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one pi and two sigma). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative n(N)->sigma*(C-C) interaction.
• Nishio, Takehiko; Tokunaga, Tatsuhiro; Omote, Yoshimori, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 405 - 407
  作者：Nishio, Takehiko、Tokunaga, Tatsuhiro、Omote, Yoshimori

  DOI：——

  日期：——