(4S,5S)-2-[(S)-1-benzyl-2-hydroxyethylimino]-4,5-diphenyl-1-ethoxycarbonylimidazolidine | 281206-88-0

• 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: (4S,5S)-2-[(S)-1-benzyl-2-hydroxyethylimino]-4,5-diphenyl-1-ethoxycarbonylimidazolidine
• 英文别名: ethyl (4S,5S)-2-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-4,5-diphenyl-4,5-dihydroimidazole-1-carboxylate
• CAS: 281206-88-0
• 化学式: C₂₇H₂₉N₃O₃
• 分子量: 443.546
• InChiKey: GHQRUUPPUFGURK-SDHOMARFSA-N

物化性质

• 沸点：
  606.4±65.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-2-[(S)-1-benzyl-2-hydroxyethylimino]-4,5-diphenyl-1-ethoxycarbonylimidazolidine 在 sodium methylate 、 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (3S,7S,8S)-3-benzyl-7,8-diphenyl-1,4,6-triazabicyclo[3.3.0]oct-4-ene
  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 四丁基氟化铵 、 2-氯-1,3-二甲基氯化咪唑啉 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 84.5h， 生成 (4S,5S)-2-[(S)-1-benzyl-2-hydroxyethylimino]-4,5-diphenyl-1-ethoxycarbonylimidazolidine
  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

• 環状グアニジン類及びその製造法
  申请人：白鳥製薬株式会社

  公开号：JP2000198775A

  公开（公告）日：2000-07-18

  (57)【要約】\n【解決手段】 次の一般式（１）\n【化１】\n〔式中、Ｒ1 〜Ｒ6 は、アルキル基等、Ｘはハロゲン原子をＢは塩基を、ｎは２又は３を示す〕で表わされる環状グアニジン類及びその製造法。\n【効果】 工業的に有利に不斉合成試薬等として有用なグアニジン類を製造し得る。

  (57) [摘要] Јn[解决方案] 由以下通式（1）Јn 代表的环胍类化合物[式中，R1 至 R6 表示烷基等，X 表示卤素原子，B 表示碱，n 表示 2 或 3]及其生产方法。\Јn [效果] 作为不对称合成试剂等有用的胍类可在工业上有利地生产。