(9R,9aS)-9-(p-toluenesulfonyl)-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: (9R,9aS)-9-(p-toluenesulfonyl)-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one
• 英文别名: (9R,9aS)-9-(4-methylphenyl)sulfonyl-1,2,5,8,9,9a-hexahydropyrrolo[1,2-a]azepin-3-one
• 化学式: C₁₆H₁₉NO₃S
• 分子量: 305.398
• InChiKey: DIKZPQOOKDPNJZ-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 Oxone 、 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.0h， 生成 (9R,9aS)-9-(p-toluenesulfonyl)-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a]azepin-3-one
  参考文献：
  名称：

  Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine

  摘要：

  The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00377-9

文献信息

• Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine
  作者：Ana Costa、Carmen Nájera、José M. Sansano

  DOI：10.1016/s0957-4166(01)00377-9

  日期：2001.8

  The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.