(1S)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛 | 302338-13-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: (1S)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛
• 中文别名: 碳酸(2:1:1)氢铵氨基甲酸酯
• 英文名称: (S)-2,2-Dimethyl-1-(2-nitro-ethyl)-cyclopentanecarbaldehyde
• 英文别名: (1S)-2,2-dimethyl-1-(2-nitroethyl)cyclopentane-1-carbaldehyde
• CAS: 302338-13-2
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: NUQRFBMQFCQZTF-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛 在 盐酸 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (5S)-(+)-6,6-dimethyl-2-azaspiro[4.4]non-1-ene
  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 在 N-乙基吗啉 、 4 Angstroem MS 作用下， 以 乙腈 、 苯 为溶剂， 生成 (1S)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛
  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.