[(1R,2R)-2-Benzyloxycarbonylamino-1,2-bis-(4-chloro-phenyl)-ethyl]-carbamic acid benzyl ester | 144406-65-5

• 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: [(1R,2R)-2-Benzyloxycarbonylamino-1,2-bis-(4-chloro-phenyl)-ethyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(1R,2R)-1,2-bis(4-chlorophenyl)-2-(phenylmethoxycarbonylamino)ethyl]carbamate
• CAS: 144406-65-5
• 化学式: C₃₀H₂₆Cl₂N₂O₄
• 分子量: 549.453
• InChiKey: ISEZQFQYHCOLJL-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯甲酸苄酯 、 (1R,2R)-1,2-双(4-氯苯基)乙烷-1,2-二胺 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-chloro-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

文献信息

• Synthesis of Nitrogen-Containing Macrocycles with Reductive Intramolecular Coupling of Aromatic Diimines
  作者：Naoki Kise、Hideaki Oike、Eiichi Okazaki、Masami Yoshimoto、Tatsuya Shono

  DOI：10.1021/jo00118a013

  日期：1995.6

  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.