(1S,1'S)-2-methyl-2-(2-nitropropyl)cyclopentanone

• 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
• 英文名称: (1S,1'S)-2-methyl-2-(2-nitropropyl)cyclopentanone
• 英文别名: (2R)-2-methyl-2-[(2R)-2-nitropropyl]cyclopentan-1-one
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: WEHILKCXUWHUPX-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基环戊酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 (1S,1'S)-2-methyl-2-(2-nitropropyl)cyclopentanone
  参考文献：
  名称：

  Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters

  摘要：

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00180-9

文献信息

• Desmaele, Didier; Cave, Christian; Dumas, Francoise, Enantiomer, 2001, vol. 6, # 5, p. 289 - 298
  作者：Desmaele, Didier、Cave, Christian、Dumas, Francoise、d'Angelo, Jean

  DOI：——

  日期：——
• Nitroalkenes as electrophiles in the asymmetric Michael reaction involving chiral imines/enamino esters
  作者：Cyrille Thominiaux、Sébastien Roussé、Didier Desmaële、Jean d'Angelo、Claude Riche

  DOI：10.1016/s0957-4166(99)00180-9

  日期：1999.5

  Addition of 2-nitropropene to the chiral imine derived from 2-methylcyclopentanone and (S)-1-phenylethylamine furnished the expected Michael adduct. The latter compound was then efficiently converted into (R)-pentalenone through a Nef reaction. Condensation of the enamino ester derived from 2-carbethoxycyclopentanone and (S)-1-phenylethylamine with 1-nitropropene gave with excellent diastereo- and enantioselectivity the corresponding Michael adduct. (C) 1999 Elsevier Science Ltd. All rights reserved.