(2R,3S,4S)-2-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one | 514205-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S)-2-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one
• 英文别名: (4S,5S,6R)-4,5,6-trihydroxy-6-methylcyclohex-2-en-1-one
• CAS: 514205-04-0
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: HAANJZCKWHVEEU-QTSITTDLSA-N

物化性质

• 沸点：
  314.8±42.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲基叔己基氯化硅 、 (2R,3S,4S)-2-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到(2R,3S,4S)-2,3-dihydroxy-4-(dimethylthexylsilyl)oxy-2-methyl-5-cyclohexen-1-one
  参考文献：
  名称：

  Asymmetric synthesis of a model compound for the cyclohexenone core of ambuic acid

  摘要：

  A model compound for the central core of ambuic acid has been prepared chemoenzymatically from toluene in enantiomerically pure form. An approach to the introduction of the C-9 side chain has also been investigated. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.023
• 作为产物：
  描述：

  (1S,2S,3S,4S)-3,4-O-isopropylidene-2-methylcyclohex-5-ene-1,2,3,4-tetraol 在 Dowex 50 WX₈-200 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (2R,3S,4S)-2-methyl-2,3,4-trihydroxy-5-cyclohexen-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral enones from aromatic compounds

  摘要：

  A series of chiral enones was successfully synthesized from chemoenzymatically produced chiral diols. These chiral enones are highly functionalized synthons, which can be used in the total synthesis of natural products such as forskolin and avermectins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00682-1

文献信息

• Chemoenzymatic synthesis of chiral enones from aromatic compounds
  作者：Valeria Schapiro、Gabriel Cavalli、Gustavo A. Seoane、Ricardo Faccio、Alvaro W. Mombrú

  DOI：10.1016/s0957-4166(02)00682-1

  日期：2002.11

  A series of chiral enones was successfully synthesized from chemoenzymatically produced chiral diols. These chiral enones are highly functionalized synthons, which can be used in the total synthesis of natural products such as forskolin and avermectins. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of a model compound for the cyclohexenone core of ambuic acid
  作者：Maitia Labora、Viviana L. Heguaburu、Enrique M. Pandolfi、Valeria Schapiro

  DOI：10.1016/j.tetasy.2008.03.023

  日期：2008.5

  A model compound for the central core of ambuic acid has been prepared chemoenzymatically from toluene in enantiomerically pure form. An approach to the introduction of the C-9 side chain has also been investigated. (C) 2008 Elsevier Ltd. All rights reserved.