4,4'-((1R,2R)-1,2-Diaminoethane-1,2-diyl)dibenzonitrile | 1055703-94-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4'-((1R,2R)-1,2-Diaminoethane-1,2-diyl)dibenzonitrile
• 英文别名: 4-[(1R,2R)-1,2-diamino-2-(4-cyanophenyl)ethyl]benzonitrile
• CAS: 1055703-94-0
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: MESREGXFTNLKRB-HZPDHXFCSA-N

物化性质

• 沸点：
  497.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸苄酯 、 4,4'-((1R,2R)-1,2-Diaminoethane-1,2-diyl)dibenzonitrile 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(1R,2R)-2-Benzyloxycarbonylamino-1,2-bis-(4-cyano-phenyl)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Nitrogen-Containing Macrocycles with Reductive Intramolecular Coupling of Aromatic Diimines

  摘要：

  Reductive intramolecular coupling of aromatic diimines is an effective method for the synthesis of a variety of nitrogen-containing macrocycles. 1,4-Diazacrown ethers 3 were effectively synthesized by intramolecular coupling of bis(imino ethers) 9 promoted by electroreduction (method A) or chemical reduction with zinc powder (method B) in the presence of methanesulfonic acid. In spite of the formation of macrocycles, the yields of 3 were relatively high. This can be explained by the formation of proton-bridged intermediates 14, in which intramolecular hydrogen bonds are formed between hydrogen and oxygen atoms of diiminium salts. Method B was more effective in the formation of 1,4-diaza-12-crown-4 derivatives 3 (n = 1) due to the template effect of Zn2+. Optically active macrocyclic bislactones 4 were synthesized stereoselectively by reductive intramolecular coupling of bis(imino esters) 20 with zinc powder (method B). The high stereoselectivity is explained by considering proton-bridged intermediate 23. The resultant compounds 4 were transformed to optically active 1,2-diarylethylenediamines 7. Various sizes of macrocyclic bislactams 5 were synthesized by reductive intramolecular coupling of bis(imino amides) 26 with zinc powder (method B). Reduction of 5 gave the corresponding macrocyclic polyamines 6.

  DOI：

  10.1021/jo00118a013
• 作为产物：
  描述：

  4-[(3S,5R,6R,8S)-6-(4-cyanophenyl)-2,9-dioxo-3,8-di(propan-2-yl)-1,10-dioxa-4,7-diazacyclotridec-5-yl]benzonitrile 在 lead(IV) acetate 、 sodium hydroxide 作用下， 生成 4,4'-((1R,2R)-1,2-Diaminoethane-1,2-diyl)dibenzonitrile
  参考文献：
  名称：

  通过还原性分子间芳族二亚胺偶联立体合成（1R，2R）-二芳基乙二胺的新方法

  摘要：

  已经发现用锌还原是从相应的手性芳族二亚胺通过其分子内偶联选择性合成（1R，2R）-二芳基乙二胺的有效方法。

  DOI：

  10.1016/s0040-4039(00)61145-0

文献信息

• Reductive coupling of aromatic oxims and azines to 1,2-diamines using Zn-MsOH or Zn-TiCl 4
  作者：Naoki Kise、Nasuo Ueda

  DOI：10.1016/s0040-4039(01)00178-2

  日期：2001.3

  The reduction of aromatic aldoxims and azines with Zn in the presence of MsOH or TiCl4 afforded N.N'-unsubstituted 1,2-diamines in one-step. The reductive coupling with Zn-MsOH gave meso 1,2-diamines selectively, whereas cll 1,2-diamines were formed selectively by the reduction with Zn-TiCl4. (C) 2001 Elsevier Science Ltd. All rights reserved.