Benzamide,N-[[(1S,3S)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropyl]methyl]- | 920338-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Benzamide,N-[[(1S,3S)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropyl]methyl]-
• 英文别名: N-[(1S,3S)-2,2-Dimethyl-3-(2-methyl-propenyl)-cyclopropylmethyl]-benzamide
• CAS: 920338-86-9
• 化学式: C₁₇H₂₃NO
• 分子量: 257.376
• InChiKey: WKPJGCWLXUTQGB-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Benzamide,N-[[(1S,3S)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropyl]methyl]- 在 臭氧 、 双氧水 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 21.5h， 以94%的产率得到(+)-(1S,3S)-3-[(benzamido)methyl]-2,2-dimethylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure geminally dimethylated cyclopropane-based C2- and pseudo-C2-symmetric diamines

  摘要：

  Enantiopure (-)-(1S,3S)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanecarboxamide 2 and (+)-(1R,3R)-2,2-dimethyl-3(2-methylprop-l-enyl)cyclopropanecarboxylic acid 3 were easily obtained from a multigram scale biotransformation of racemic amide or nitrile in the presence of Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions. Coupled with efficient and convenient chemical manipulations, comprising mainly of the Curtius rearrangement, oxidation, and reduction reactions, chiral C-2-symmetric (1S,2S)-3,3-dimethylcyclopropane-1,2-diamine 6 and ((1R,3R)-3-(aminomethyl)-2,2-dimethylcyclopropyl)methanamine 8 and pseudo-C-2-symmetric (1S,3S)-3-(aminomethyl)-2,2-dimethylcyclopropanamine 11 were prepared. These were also transformed into the corresponding chiral salen derivatives 12, 13, and 14, respectively, in almost quantitative yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.030
• 作为产物：
  描述：

  (+/-)-trans-2,2-dimethyl-3-(2',2'-dimethylvinyl)cyclopropanecarbonitrile 在 lithium aluminium tetrahydride 、 Rhodococcus erythropolis AJ₂₇₀ cells 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 Benzamide,N-[[(1S,3S)-2,2-dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropyl]methyl]-
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure geminally dimethylated cyclopropane-based C2- and pseudo-C2-symmetric diamines

  摘要：

  Enantiopure (-)-(1S,3S)-2,2-dimethyl-3-(2-methylprop-l-enyl)cyclopropanecarboxamide 2 and (+)-(1R,3R)-2,2-dimethyl-3(2-methylprop-l-enyl)cyclopropanecarboxylic acid 3 were easily obtained from a multigram scale biotransformation of racemic amide or nitrile in the presence of Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions. Coupled with efficient and convenient chemical manipulations, comprising mainly of the Curtius rearrangement, oxidation, and reduction reactions, chiral C-2-symmetric (1S,2S)-3,3-dimethylcyclopropane-1,2-diamine 6 and ((1R,3R)-3-(aminomethyl)-2,2-dimethylcyclopropyl)methanamine 8 and pseudo-C-2-symmetric (1S,3S)-3-(aminomethyl)-2,2-dimethylcyclopropanamine 11 were prepared. These were also transformed into the corresponding chiral salen derivatives 12, 13, and 14, respectively, in almost quantitative yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.030