(1S,2S)-3-chloro-1,2-O-isopropylidenecyclohex-3-ene-1,2-diol | 852108-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-3-chloro-1,2-O-isopropylidenecyclohex-3-ene-1,2-diol
• 英文别名: (3aS,7aS)-7-chloro-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole
• CAS: 852108-52-2
• 化学式: C₉H₁₃ClO₂
• 分子量: 188.654
• InChiKey: XFPGKUIAUJFKKB-JGVFFNPUSA-N

物化性质

• 沸点：
  242.0±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S)-3-chloro-1,2-O-isopropylidenecyclohex-3-ene-1,2-diol 在 2,6-二甲基吡啶 、 sodium azide 、 Dowex 50W₈-200 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 31.0h， 生成 (2S,3S,6S)-6-azido-2-(tert-butyldimethylsilyloxy)-3-(methoxymethyloxy)cyclohexan-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds

  摘要：

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.012
• 作为产物：
  描述：

  (1S-顺式)-3-氯-3,5-环己二烯-1,2-二醇 在 potassium diazodicarboxylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 (1S,2S)-3-chloro-1,2-O-isopropylidenecyclohex-3-ene-1,2-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds

  摘要：

  A series of chiral alpha-substituted cyclohexanones have been synthesized from chemoenzymatically produced chlorocyclo-hexadienediol. These highly functionalized ketones can be used in the total synthesis of diverse natural products, such as bengamides. A study of the reactivity of alpha-chlorooxiranes, common intermediates in the synthetic scheme, showed that under nucleophilic opening conditions an intermediate chloroketone may or may not form, depending on the nature of the nucleophiles present in the reaction medium. The stereochemical outcome of this reaction is presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.012

文献信息

• A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277
  作者：Andrew Lin、Anthony C. Willis、Martin G. Banwell

  DOI：10.1016/j.tetlet.2009.12.067

  日期：2010.2

  The structure, 5, assigned to the resorcylic acid lactone L-783,290 has been prepared for the first time and in a modular fashion using a Heck reaction to link the readily available fragments 8 and 14. Chemoenzymatic methods were used to prepare the latter fragment, in enantiopure form, from chlorobenzene. (C) 2009 Elsevier Ltd. All rights reserved.