N-[(S)-1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]-N'-[(S)-1-benzyl-2-hydroxyethyl]-N''-[(S)-1-phenylethyl]guanidine | 314050-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(S)-1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]-N'-[(S)-1-benzyl-2-hydroxyethyl]-N''-[(S)-1-phenylethyl]guanidine
• 英文别名: 1-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropan-2-yl]-3-[(2S)-1-hydroxy-3-phenylpropan-2-yl]-2-[(1S)-1-phenylethyl]guanidine
• CAS: 314050-73-2
• 化学式: C₃₃H₄₇N₃O₂Si
• 分子量: 545.841
• InChiKey: BSTBEGQOSZYKQV-JOYXZSCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(S)-1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]-N'-[(S)-1-benzyl-2-hydroxyethyl]-N''-[(S)-1-phenylethyl]guanidine 在 甲烷磺酸 、 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 、 氢氧化钾 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 4.17h， 生成 (3S,8S)-3,8-dibenzyl-6-[(S)-1-phenylethyl]-1,4,6-triazabicyclo[3.3.0]oct-4-ene 、 4-benzyl-1-[1-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropan-2-yl]-N-(1-phenylethyl)-4,5-dihydroimidazol-2-amine 、 4-benzyl-N-[1-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropan-2-yl]-1-(1-phenylethyl)-4,5-dihydroimidazol-2-amine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 3. Preparation of 1,4,6-Triazabicyclooctene Systems and 1,4-Disubstituted 2-Iminoimidazolidines by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines with a Hydroxyethyl Substituent

  摘要：

  Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7,8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1,3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and then of 2-(2-hydroxyethylimino)imidazolidines to the bicyclic systems. Linear guanidines with a 2-hydroxyethyl functional group were prepared by the reaction of carbodiimides with 2-amino alcohols. Reaction of linear-type guanidines with DMC followed by base treatment afforded 1,4-disubstitued 2-iminoimidazolidines. Furthermore, another type of 1,4,6-triazabicyclooctene was also prepared through double DMC-induced cyclization of guanidines with two a-hydroxyethyl substituents.

  DOI：

  10.1021/jo000746f
• 作为产物：
  描述：

  (S)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-amine 在 D-青霉胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 37.5h， 生成 N-[(S)-1-benzyl-2-(tert-butyldimethylsilyloxy)ethyl]-N'-[(S)-1-benzyl-2-hydroxyethyl]-N''-[(S)-1-phenylethyl]guanidine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 3. Preparation of 1,4,6-Triazabicyclooctene Systems and 1,4-Disubstituted 2-Iminoimidazolidines by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines with a Hydroxyethyl Substituent

  摘要：

  Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7,8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1,3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and then of 2-(2-hydroxyethylimino)imidazolidines to the bicyclic systems. Linear guanidines with a 2-hydroxyethyl functional group were prepared by the reaction of carbodiimides with 2-amino alcohols. Reaction of linear-type guanidines with DMC followed by base treatment afforded 1,4-disubstitued 2-iminoimidazolidines. Furthermore, another type of 1,4,6-triazabicyclooctene was also prepared through double DMC-induced cyclization of guanidines with two a-hydroxyethyl substituents.

  DOI：

  10.1021/jo000746f

文献信息

• Modified Guanidines as Potential Chiral Superbases. 3. Preparation of 1,4,6-Triazabicyclooctene Systems and 1,4-Disubstituted 2-Iminoimidazolidines by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines with a Hydroxyethyl Substituent
  作者：Toshio Isobe、Keiko Fukuda、Kentaro Yamaguchi、Hiroko Seki、Tatsuhiro Tokunaga、Tsutomu Ishikawa

  DOI：10.1021/jo000746f

  日期：2000.11.1

  Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7,8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1,3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and then of 2-(2-hydroxyethylimino)imidazolidines to the bicyclic systems. Linear guanidines with a 2-hydroxyethyl functional group were prepared by the reaction of carbodiimides with 2-amino alcohols. Reaction of linear-type guanidines with DMC followed by base treatment afforded 1,4-disubstitued 2-iminoimidazolidines. Furthermore, another type of 1,4,6-triazabicyclooctene was also prepared through double DMC-induced cyclization of guanidines with two a-hydroxyethyl substituents.