N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-cyclohexylthiourea | 313695-74-8

• 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: N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-cyclohexylthiourea
• 英文别名: 1-[(1S,2S)-2-amino-1,2-diphenylethyl]-3-cyclohexylthiourea
• CAS: 313695-74-8
• 化学式: C₂₁H₂₇N₃S
• 分子量: 353.531
• InChiKey: AJTZMUPNWNPMGH-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-cyclohexylthiourea 在 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (4S,5S)-1-benzyloxycarbonyl-2-cyclohexylimino-4,5-diphenylimidazolidine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n
• 作为产物：
  描述：

  (1S,2S)-1,2-二苯基乙二胺 、 环己基异硫氰酸脂 以 乙腈 为溶剂， 反应 24.0h， 以83%的产率得到N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-cyclohexylthiourea
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n
• 作为试剂：
  描述：

  反式硝基苯乙烯 、 苯乙酮 在 N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-cyclohexylthiourea 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-1,3-diphenyl-4-nitrobutane-1-one 、 (S)-4-nitro-1,3-diphenylbutan-1-one
  参考文献：
  名称：

  基于天然氨基酸叔丁基酯的伯胺-硫脲作为迈克尔反应的有机催化剂

  摘要：

  Abstractmagnified imageA new class of primary amine‐thioureas based on tert‐butyl esters of (S)‐α‐amino acids and (1S,2S)‐diphenylethylenediamine was synthesized and their activity as catalysts in Michael additions was evaluated. Derivatives based on di‐tert‐butyl aspartate and tert‐butyl O‐tert‐butyl threoninate provided the product of the reaction between trans‐β‐nitrostyrene and acetone in quantitative yield and high enantioselectivity (87–91% ee). All the thioureas based on tert‐butyl esters of amino acids catalyzed the reaction of nitroolefins with acetophenone with high enantioselectivity (92–98% ee). Thus, low‐cost, commercially available tert‐butyl esters of natural amino acids are very important chiral building blocks for the construction of novel chiral thioureas able to catalyze asymmetric Michael additions with high enantioselectivity.

  DOI：

  10.1002/adsc.200800812