(R)-2-carbethoxy-2-cyclohexen-1-ol | 144901-82-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (R)-2-carbethoxy-2-cyclohexen-1-ol
• 英文别名: ethyl (6R)-6-hydroxycyclohexene-1-carboxylate
• CAS: 144901-82-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: UBESRLLLKNDABE-MRVPVSSYSA-N

物化性质

• 沸点：
  267.0±40.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (6R)-6-acetyloxycyclohexene-1-carboxylate 以 丙酮 为溶剂， 反应 100.0h， 以92.5%的产率得到(R)-2-carbethoxy-2-cyclohexen-1-ol
  参考文献：
  名称：

  Enantiocomplementary synthesis of functionalized cycloalkenol building blocks using lipase

  摘要：

  Racemic 2-carbethoxy-2-cyclopenten-1-ol [(+/-)-3a] and racemic 2-carbethoxy-2-cyclohexen-1-ol [(+/-)-3b] afforded the corresponding (R)-acetates [(R)-4a and (R)-4b] leaving the corresponding (S)-alcohols [(S)-3a and (S)-3b] unchanged upon treatment with vinyl acetate in tert-butyl methyl ether in the presence of lipase PS, respectively, while the racemic acetates [(+/-)-4a and (+/-)-4b], derived from racemic precursors, (+/-)-3a and (+/-)-3b, on suspension with lipase in a phosphate buffer solution afforded the corresponding (R)-alcohols [(R)-3a and (R)-3b] leaving the corresponding (S)-acetates [(S)-4a and (S)-4b] unchanged, respectively.

  DOI：

  10.1016/s0957-4166(00)82178-3

文献信息

• An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis–Hillman reaction
  作者：Shang-Hung Chen、Bor-Cherng Hong、Cheng-Feng Su、Sepehr Sarshar

  DOI：10.1016/j.tetlet.2005.10.072

  日期：2005.12

  A highly enantioselective proline catalyzed intramolecular Baylis-Hillman reaction of hept-2-enedial is reported. Addition of imidazole to the mixture results in art unusual inversion of enantioselectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantiocomplementary synthesis of functionalized cycloalkenol building blocks using lipase
  作者：Seiichi Takano、Takahiro Yamane、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)82178-3

  日期：1992.7

  Racemic 2-carbethoxy-2-cyclopenten-1-ol [(+/-)-3a] and racemic 2-carbethoxy-2-cyclohexen-1-ol [(+/-)-3b] afforded the corresponding (R)-acetates [(R)-4a and (R)-4b] leaving the corresponding (S)-alcohols [(S)-3a and (S)-3b] unchanged upon treatment with vinyl acetate in tert-butyl methyl ether in the presence of lipase PS, respectively, while the racemic acetates [(+/-)-4a and (+/-)-4b], derived from racemic precursors, (+/-)-3a and (+/-)-3b, on suspension with lipase in a phosphate buffer solution afforded the corresponding (R)-alcohols [(R)-3a and (R)-3b] leaving the corresponding (S)-acetates [(S)-4a and (S)-4b] unchanged, respectively.