(2S,3S,6R)-6-hydroxy-2,3-isopropylidenedioxycyclohexanone | 743444-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,6R)-6-hydroxy-2,3-isopropylidenedioxycyclohexanone
• 英文别名: (3aS,5R,7aS)-Tetrahydro-5-hydroxy-2,2-dimethyl-1,3-benzodioxol-4(3aH)-one；(3aS,5R,7aS)-5-hydroxy-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one
• CAS: 743444-66-8
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VTSDXZJNBJULGA-CHKWXVPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,6R)-6-hydroxy-2,3-isopropylidenedioxycyclohexanone 在 sodium azide 、 Dowex 50W₈-200 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (2S,3S,6S)-6-azido-2,3-dihydroxycyclohexan-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 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 10.08h， 生成 (2S,3S,6R)-6-hydroxy-2,3-isopropylidenedioxycyclohexanone
  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

• Microwave-assisted, solvent-free oxidative cleavage of α-hydroxyketones
  作者：Ignacio Carrera、Margarita C. Brovetto、Juan Carlos Ramos、Gustavo A. Seoane

  DOI：10.1016/j.tetlet.2009.07.048

  日期：2009.9

  The oxidative C-C cleavage of alpha-hydroxy ketones was found to proceed smoothly in solvent-free, silica-supported sodium metaperiodate, under Microwave irradiation. This provides a useful and green synthetic procedure to form the corresponding carboxylic acid and aldehyde in good yields, avoiding the solubility problems of the sodium metaperiodate in organic solvents. (C) 2009 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of enantiopure α-substituted cyclohexanones from aromatic compounds
  作者：Germán Fonseca、Gustavo A. Seoane

  DOI：10.1016/j.tetasy.2005.02.012

  日期：2005.4

  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.