(1S,2S)-2-methyl-2-(1-methylethenyl)cyclopropanecarboxylic acid | 1310822-42-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S)-2-methyl-2-(1-methylethenyl)cyclopropanecarboxylic acid
• 英文别名: (1S,2S)-2-methyl-2-prop-1-en-2-ylcyclopropane-1-carboxylic acid
• CAS: 1310822-42-4
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: BGSHFZLVGCJRJC-HTRCEHHLSA-N

物化性质

• 沸点：
  217.9±29.0 °C(predicted)
• 密度：
  1.082±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  trans-ethyl 2-methyl-2-(prop-1-en-2-yl)cyclopropanecarboxylate 在 (1S,2S)-(+)-2-(dimethylamino)-1-[4-(methylthio)phenyl]propane-1,3-diol 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 异丙醚 、 水 为溶剂， 反应 48.5h， 生成 (rac)-(1S,2S)-2-methyl-2-(1-methylethenyl)cyclopropanecarboxylic acid 、 (1S,2S)-2-methyl-2-(1-methylethenyl)cyclopropanecarboxylic acid
  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.