(S)-(-)-N-methyl-1-benzyloxycarbonylaziridine-2-carboxamide

• 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: (S)-(-)-N-methyl-1-benzyloxycarbonylaziridine-2-carboxamide
• 英文别名: benzyl (2R)-2-(methylcarbamoyl)aziridine-1-carboxylate
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: FEVABTGFCOODHB-IAPIXIRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-methyl-1-benzyloxycarbonylaziridine-2-carboxamide 在 盐酸 、 硫酸 、 硼烷 、 sodium cyanoborohydride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 86.0h， 生成 (R)-6-benzyloxycarbonylamino-1-methyl-4-(3-methylbenzyl)hexahydro-1,4-diazepine
  参考文献：
  名称：

  Efficient synthesis of (R)-6-benzyloxycarbonylamino-1-methyl-4-(3-methyl-benzyl)hexahydro-1,4-diazepine. 2. Novel formation of hexahydro-1,4-diazepine ring using 1,2,3-trisubstituted aminopropane derivative and glyoxal

  摘要：

  An efficient and practical method for synthesis of the optically active hexahydro-1,4-diazepine 2, which is a key intermediate of DAT-582, a potent and selective serotonin-3 receptor antagonist, is described Treatment of the (R)-1,2,3-trisubstituted aminopropane dihydrochloride 5b prepared from methyl (S)-1-tritylaziridne-2-carboxylate (4) via the (S)-1-benzyloxycarbonylaziridine-2-carboximide 8 with glyoxal in the presence of NaBH3CN or boran-triethylamine complex directly gave 2 in good yield without racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00616-4
• 作为产物：
  描述：

  氯甲酸苄酯 、 (S)-N-methylaziridine-2-carboxamide 以 氯仿 为溶剂， 反应 5.0h， 生成 (S)-(-)-N-methyl-1-benzyloxycarbonylaziridine-2-carboxamide
  参考文献：
  名称：

  Efficient synthesis of (R)-6-benzyloxycarbonylamino-1-methyl-4-(3-methyl-benzyl)hexahydro-1,4-diazepine. 2. Novel formation of hexahydro-1,4-diazepine ring using 1,2,3-trisubstituted aminopropane derivative and glyoxal

  摘要：

  An efficient and practical method for synthesis of the optically active hexahydro-1,4-diazepine 2, which is a key intermediate of DAT-582, a potent and selective serotonin-3 receptor antagonist, is described Treatment of the (R)-1,2,3-trisubstituted aminopropane dihydrochloride 5b prepared from methyl (S)-1-tritylaziridne-2-carboxylate (4) via the (S)-1-benzyloxycarbonylaziridine-2-carboximide 8 with glyoxal in the presence of NaBH3CN or boran-triethylamine complex directly gave 2 in good yield without racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00616-4

文献信息

• Efficient synthesis of (R)-6-benzyloxycarbonylamino-1-methyl-4-(3-methyl-benzyl)hexahydro-1,4-diazepine. 2. Novel formation of hexahydro-1,4-diazepine ring using 1,2,3-trisubstituted aminopropane derivative and glyoxal
  作者：Hiroshi Harada、Toshiya Morie、Toshifumi Suzuki、Toyokichi Yoshida、Shiro Kato

  DOI：10.1016/s0040-4020(98)00616-4

  日期：1998.9

  An efficient and practical method for synthesis of the optically active hexahydro-1,4-diazepine 2, which is a key intermediate of DAT-582, a potent and selective serotonin-3 receptor antagonist, is described Treatment of the (R)-1,2,3-trisubstituted aminopropane dihydrochloride 5b prepared from methyl (S)-1-tritylaziridne-2-carboxylate (4) via the (S)-1-benzyloxycarbonylaziridine-2-carboximide 8 with glyoxal in the presence of NaBH3CN or boran-triethylamine complex directly gave 2 in good yield without racemization. (C) 1998 Elsevier Science Ltd. All rights reserved.