(E)-5-[(3aR,5R,6S,6aR)-6-(Imidazole-1-carbothioyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-pent-2-enoic acid methyl ester | 151426-59-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-5-[(3aR,5R,6S,6aR)-6-(Imidazole-1-carbothioyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-pent-2-enoic acid methyl ester
• CAS: 151426-59-4
• 化学式: C₁₇H₂₂N₂O₆S
• 分子量: 382.437
• InChiKey: YQNUCSHGFBKGQT-DVTRTIFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  81.04
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (E)-5-[(3aR,5R,6S,6aR)-6-(Imidazole-1-carbothioyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-pent-2-enoic acid methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以88%的产率得到methyl 2-[(1S,2R,6R,8R,11R)-4,4-dimethyl-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-11-yl]acetate
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8
• 作为产物：
  描述：

  5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-heptodialdo-1,4-furanose 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (E)-5-[(3aR,5R,6S,6aR)-6-(Imidazole-1-carbothioyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates

  摘要：

  The tributyltin hydride + azobisisobutyronitrile (AIBN) mediated free radical carbocyclization of precursors 1-9, 48 and 49 is described. The resulting carbocycles have been obtained in moderate yield and good diastereoselectivity. These polyfunctionalized, enantiomerically pure cyclopentane derivatives are useful intermediates for further manipulation.

  DOI：

  10.1016/s0040-4020(01)81837-8