ethyl (2S,3S)-3-benzyl-1-[(S)-1-phenylethyl]aziridine-2-carboxylate | 389631-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S,3S)-3-benzyl-1-[(S)-1-phenylethyl]aziridine-2-carboxylate
• 英文别名: ethyl (2S,3S)-3-benzyl-1-[(1S)-1-phenylethyl]aziridine-2-carboxylate
• CAS: 389631-11-2
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: AXEIEISYJZOGAR-MKBFOZKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S)-3-benzyl-1-[(S)-1-phenylethyl]aziridine-2-carboxylate 在 palladium dihydroxide ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 氢气 、 potassium carbonate 作用下， 以 四氯化碳 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 (2S)-[N-(tert-butoxycarbonyl)amino]-4-phenylmethyl butanoate
  参考文献：
  名称：

  New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates

  摘要：

  Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of alpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, beta -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-beta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00823-7
• 作为产物：
  描述：

  重氮乙酸乙酯 、 3-phenyl-2-<(S)-1-phenylethylamino>propanenitrile 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl (2R,3R)-3-benzyl-1-[(S)-1-phenylethyl]aziridine-2-carboxylate 、 ethyl (2S,3S)-3-benzyl-1-[(S)-1-phenylethyl]aziridine-2-carboxylate
  参考文献：
  名称：

  New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates

  摘要：

  Syntheses of cis-3-alkylaziridine-2-carboxylates including cis-3-benzyl- and cis-3-phenylaziridine-2-carboxylates were achieved from the reaction of alpha -aminonitrile and alkyldiazoacetate in the presence of a Lewis acid. Asymmetric version of this reaction with the chiral alpha -methylbenzylamine was also successful for the preparation of chiral aziridines that were used for the synthesis of various amino acids including homophenylalanine, beta -amino-alpha -hydroxy acid, alpha,beta -diamino acid, and alpha -amino-beta -hydroxy acid via regioselective aziridine ring openings. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00823-7