(1R,4R,5R)-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol | 676543-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1R,4R,5R)-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol
• 英文别名: 2,3-Dioxabicyclo[2.2.2]oct-7-en-5-ol, (1R,4R,5R)-
• CAS: 676543-79-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: DRRIYZQOHCHRML-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide 在 titanium(IV) isopropylate 、 二甲基硫 、 Candida cylindracea lipase VII 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (1R,4R,5R)-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol
  参考文献：
  名称：

  Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (−)- and (+)-proto-quercitol

  摘要：

  Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.037

文献信息

• Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: synthesis of (−)- and (+)-proto-quercitol
  作者：M.Serdar Gültekin、Murat Çelik、Engin Turkut、Cihangir Tanyeli、Metin Balci

  DOI：10.1016/j.tetasy.2003.11.037

  日期：2004.2

  Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce ()-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (+/-)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively. (C) 2003 Elsevier Ltd. All rights reserved.