(1S,7aR)-1-[(4S,5R)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one | 214400-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,7aR)-1-[(4S,5R)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 214400-44-9
• 化学式: C₁₂H₁₈ClNO₄
• 分子量: 275.732
• InChiKey: NYDYRECLSXFVFH-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,7aR)-1-[(4S,5R)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以83%的产率得到(3aS,8aR,9S,9aS)-2,2-dimethyl-octahydro[1,3]dioxolo[4,5-f]indolizin-9-ol
  参考文献：
  名称：

  Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine

  摘要：

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01491-9
• 作为产物：
  描述：

  1-Boc-四氢吡咯 在 palladium on activated charcoal 四氯化碳 、 氢气 、 仲丁基锂 、 sodium hydride 、 potassium carbonate 、 三苯基膦 、 鹰爪豆碱 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 (1S,7aR)-1-[(4S,5R)-5-(chloromethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
  参考文献：
  名称：

  Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine

  摘要：

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01491-9

文献信息

• Stereoselective synthesis of hydroxyindolizidines via sparteine-assisted deprotonation of N-Boc-pyrrolidine
  作者：Marek Majewski、Jianxing Shao、Ken Nelson、Pawel Nowak、Nicholas M. Irvine

  DOI：10.1016/s0040-4039(98)01491-9

  日期：1998.9

  Three diastereoisomers of 1-deoxycastanospermine were synthesized in enantiomerically pure form. The key step in the synthesis involved reaction of lithiated N-Boc-pyrrolidine in the presence of sparteine with a chiral building block derived from tartaric acid. (C) 1998 Elsevier Science Ltd. All rights reserved.