(1R)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛 | 325705-65-5

• 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: (1R)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛
• 中文别名: 乙基1-苯甲基-5-羟基-1H-1,2,3-三唑-4-羧酸酯
• 英文名称: (R)-2,2-Dimethyl-1-(2-nitro-ethyl)-cyclopentanecarbaldehyde
• 英文别名: (1R)-2,2-dimethyl-1-(2-nitroethyl)cyclopentane-1-carbaldehyde
• CAS: 325705-65-5
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: NUQRFBMQFCQZTF-JTQLQIEISA-N

物化性质

• 沸点：
  289.9±13.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

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：

  (1R)-2,2-二甲基-1-(2-硝基乙基)环戊烷甲醛 在 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 2-((R)-1-[1,3]Dioxolan-2-yl-2,2-dimethyl-cyclopentyl)-ethylamine
  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-nitroethyl acetate 、 (R)-1-[2,2-Dimethyl-cyclopent-(E)-ylidenemethyl]-2-methoxymethyl-pyrrolidine 在 N-乙基吗啉 作用下， 以 乙腈 为溶剂， 生成 (1R)-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.