N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-benzylthiourea | 313695-73-7

• 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'-benzylthiourea
• 英文别名: 1-((1S,2S)-2-amino-1,2-diphenylethyl)-3-benzylthiourea；1-[(1S,2S)-2-amino-1,2-diphenylethyl]-3-benzylthiourea
• CAS: 313695-73-7
• 化学式: C₂₂H₂₃N₃S
• 分子量: 361.511
• InChiKey: GOEWFHXLCOMDKQ-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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'-benzylthiourea 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-benzoyl-2-benzylimino-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 、 异硫氰酸苯甲酯 以 二氯甲烷 为溶剂， 反应 96.0h， 以71%的产率得到N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-benzylthiourea
  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：

  4-羟基香豆素 、 苄叉丙酮 在 N-[(1S,2S)-2-amino-1,2-diphenylethyl]-N'-benzylthiourea 作用下， 以 1,4-二氧六环 为溶剂， 反应 55.0h， 以97%的产率得到(S)-(-)-华法令
  参考文献：
  名称：

  简单手性伯胺硫脲双功能催化剂促进的α-β-不饱和酮高效和对映选择性Michael加成4-羟基香豆素

  摘要：

  开发了4-羟基香豆素在手性伯胺硫脲双功能催化剂促进的α，β-不饱和酮上的高度不对称迈克尔加成反应，并获得了一系列迈克尔加合物，收率极高（高达97％）和对映选择性（高达95％ee） ）。一次重结晶后，很容易在99％ee中获得光学纯的S-华法林。

  DOI：

  10.1016/j.tetlet.2011.01.054

文献信息

• Application of “Hydrogen Bonding Interaction” in New Drug Development: Design, Synthesis, Antiviral Activity, and SARs of Thiourea Derivatives
  作者：Aidang Lu、Ziwen Wang、Zhenghong Zhou、Jianxin Chen、Qingmin Wang

  DOI：10.1021/jf505355r

  日期：2015.2.11

  A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 mu g/mL and 39%/100 mu g/mL; inactivation activity, 71%/500 mu g/mL and 35%/100 mu g/mL; curative activity, 73%/500 mu g/mL and 37%/100 mu g/mL; protection activity, 69%/500 mu g/mL and 33%/100 mu g/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.
• 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
  作者：Toshio Isobe、Keiko Fukuda、Tatsuhiro Tokunaga、Hiroko Seki、Kentaro Yamaguchi、Tsutomu Ishikawa

  DOI：10.1021/jo000745n

  日期：2000.11.1

  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.