1-[(1S,2S)-2-methyl-2-(1-methylethenyl)-cyclopropyl]ethanone | 1310822-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1S,2S)-2-methyl-2-(1-methylethenyl)-cyclopropyl]ethanone
• 英文别名: 1-[(1S,2S)-2-methyl-2-prop-1-en-2-ylcyclopropyl]ethanone
• CAS: 1310822-44-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: BCMSQFDOWTYHOB-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(1S,2S)-2-methyl-2-(1-methylethenyl)-cyclopropyl]ethanone 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 生成 2-[(1S,2S)-2-methyl-2-(1-methylethenyl)-cyclopropyl]but-3-yn-2-yl acetate
  参考文献：
  名称：

  Unexpected Cycloisomerizations of Nonclassical Carbocation Intermediates in Gold(I)-Catalyzed Homo-Rautenstrauch Cyclizations

  摘要：

  An unexpected gold(I)-catalyzed homo-Rautenstrauch rearrangement of 1-cyclopropyl propargylic esters to cyclohexenones is disclosed. This rearrangement represents new evidence for the recently discussed gold-stabilized non-classical carbocation character of intermediates in gold catalysis. A mechanistic study proved partial chirality transfer from optically active propargyl acetates.

  DOI：

  10.1021/jo200416d
• 作为产物：
  描述：

  (1S,2S)-2-methyl-2-(1-methylethenyl)cyclopropanecarboxylic acid 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-[(1S,2S)-2-methyl-2-(1-methylethenyl)-cyclopropyl]ethanone
  参考文献：
  名称：

  Unexpected Cycloisomerizations of Nonclassical Carbocation Intermediates in Gold(I)-Catalyzed Homo-Rautenstrauch Cyclizations

  摘要：

  An unexpected gold(I)-catalyzed homo-Rautenstrauch rearrangement of 1-cyclopropyl propargylic esters to cyclohexenones is disclosed. This rearrangement represents new evidence for the recently discussed gold-stabilized non-classical carbocation character of intermediates in gold catalysis. A mechanistic study proved partial chirality transfer from optically active propargyl acetates.

  DOI：

  10.1021/jo200416d

文献信息

• Unexpected Cycloisomerizations of Nonclassical Carbocation Intermediates in Gold(I)-Catalyzed Homo-Rautenstrauch Cyclizations
  作者：Guan Wang、Yue Zou、Zhiming Li、Quanrui Wang、Andreas Goeke

  DOI：10.1021/jo200416d

  日期：2011.7.15

  An unexpected gold(I)-catalyzed homo-Rautenstrauch rearrangement of 1-cyclopropyl propargylic esters to cyclohexenones is disclosed. This rearrangement represents new evidence for the recently discussed gold-stabilized non-classical carbocation character of intermediates in gold catalysis. A mechanistic study proved partial chirality transfer from optically active propargyl acetates.