(2S)-1-[(E)-(2,2-dimethylcyclopentylidene)methyl]-2-(methoxymethyl)pyrrolidine | 325705-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S)-1-[(E)-(2,2-dimethylcyclopentylidene)methyl]-2-(methoxymethyl)pyrrolidine
• CAS: 325705-63-3
• 化学式: C₁₄H₂₅NO
• 分子量: 223.359
• InChiKey: RRGUUQJSGONPQU-XSNHNAGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-1-[(E)-(2,2-dimethylcyclopentylidene)methyl]-2-(methoxymethyl)pyrrolidine 在 N-乙基吗啉 、 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (4S,5R,6S)-(+)-2',2'-dimethyl-6-nitrospiro{1-azabicyclo[3.3.0]octane-4,1'-cyclopentane}
  参考文献：
  名称：

  Enantioselective synthesis of polyzonimine and nitropolyzonamine, spirocyclic compounds from the defensive glands of a millipede, Polyzonium rosalbum

  摘要：

  Asymmetric Michael addition of the enamine derived from 2,2-dimethylcyclopentanecarboxaldehyde and (S)-prolinol methyl ether to nitroethylene afforded the adduct of 76% ee, which finally yielded enantiomerically pure (+)-polyzonimine and (+)-nitropolyzonamine, compounds from the defensive glands of a millipede, Polyzonium rosalbum. The absolute configuration of (+)-polyzonimine was determined as S, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01133-3
• 作为产物：
  描述：

  2,2-dimethylcyclopentanecarboxaldehyde 、 (S)-(+)-2-(甲氧基甲基)吡唑烷 在 4 Angstroem MS 作用下， 以 苯 为溶剂， 生成 (2S)-1-[(E)-(2,2-dimethylcyclopentylidene)methyl]-2-(methoxymethyl)pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of polyzonimine and nitropolyzonamine, spirocyclic compounds from the defensive glands of a millipede, Polyzonium rosalbum

  摘要：

  Asymmetric Michael addition of the enamine derived from 2,2-dimethylcyclopentanecarboxaldehyde and (S)-prolinol methyl ether to nitroethylene afforded the adduct of 76% ee, which finally yielded enantiomerically pure (+)-polyzonimine and (+)-nitropolyzonamine, compounds from the defensive glands of a millipede, Polyzonium rosalbum. The absolute configuration of (+)-polyzonimine was determined as S, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01133-3

文献信息

• Enantioselective synthesis of polyzonimine and nitropolyzonamine, spirocyclic compounds from the defensive glands of a millipede, Polyzonium rosalbum
  作者：Kenji Mori、Yasuyo Takagi

  DOI：10.1016/s0040-4039(00)01133-3

  日期：2000.8

  Asymmetric Michael addition of the enamine derived from 2,2-dimethylcyclopentanecarboxaldehyde and (S)-prolinol methyl ether to nitroethylene afforded the adduct of 76% ee, which finally yielded enantiomerically pure (+)-polyzonimine and (+)-nitropolyzonamine, compounds from the defensive glands of a millipede, Polyzonium rosalbum. The absolute configuration of (+)-polyzonimine was determined as S, (C) 2000 Elsevier Science Ltd. All rights reserved.