(5S,6S)-4,8-dioxo-2-(trichloromethyl)-1,3,7-trioxaspiro[4,4]nonane-6-carboxylic acid

• 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: (5S,6S)-4,8-dioxo-2-(trichloromethyl)-1,3,7-trioxaspiro[4,4]nonane-6-carboxylic acid
• 英文别名: (5S,6S)-4,8-dioxo-2-(trichloromethyl)-1,3,7-trioxaspiro[4.4]nonane-6-carboxylic acid
• 化学式: C₈H₅Cl₃O₇
• 分子量: 319.482
• InChiKey: ZLRCAQMEFRZDBR-MKBTXFHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,6S)-4,8-dioxo-2-(trichloromethyl)-1,3,7-trioxaspiro[4,4]nonane-6-carboxylic acid 在 borane methyl suphide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以72%的产率得到(3aS,6aS)-3-hydroxytetrahydrofuro[3,4-b]furan-2,4-dione
  参考文献：
  名称：

  Synthesis of enantiopure concave (+)-avenaciolide and (−)-canadensolide skeletons

  摘要：

  Simultaneous regio- and chemoselective reduction of the carboxyl group of (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (garcinia acid), isolated from plant sources in large amounts, has been carried out to reach the core concave bislactone structures of fungal metabolites (+)-avenaciolide and (-)-canadensolide in one and two steps, respectively. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.081
• 作为产物：
  描述：

  三氯乙醛 、 藤黄内酯 在 硫酸 作用下， 以89.5%的产率得到(5S,6S)-4,8-dioxo-2-(trichloromethyl)-1,3,7-trioxaspiro[4,4]nonane-6-carboxylic acid
  参考文献：
  名称：

  Synthesis of enantiopure concave (+)-avenaciolide and (−)-canadensolide skeletons

  摘要：

  Simultaneous regio- and chemoselective reduction of the carboxyl group of (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (garcinia acid), isolated from plant sources in large amounts, has been carried out to reach the core concave bislactone structures of fungal metabolites (+)-avenaciolide and (-)-canadensolide in one and two steps, respectively. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.081

文献信息

• Synthesis of enantiopure concave (+)-avenaciolide and (−)-canadensolide skeletons
  作者：Susan Varugese、Salini Thomas、Simimole Haleema、TomThomas Puthiaparambil、Ibrahim Ibnusaud

  DOI：10.1016/j.tetlet.2007.09.081

  日期：2007.11

  Simultaneous regio- and chemoselective reduction of the carboxyl group of (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (garcinia acid), isolated from plant sources in large amounts, has been carried out to reach the core concave bislactone structures of fungal metabolites (+)-avenaciolide and (-)-canadensolide in one and two steps, respectively. (C) 2007 Elsevier Ltd. All rights reserved.