(3aR,5S,6S,6aR)-5-(iodomethyl)-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol | 151426-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5S,6S,6aR)-5-(iodomethyl)-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
• CAS: 151426-64-1
• 化学式: C₁₁H₁₇IO₄
• 分子量: 340.158
• InChiKey: IACLYOGHQWCDMP-PKIKSRDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6S,6aR)-5-(iodomethyl)-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 以14 mg的产率得到(1R,2R,6R,8R,10S)-4,4,10-trimethyl-3,5,7-trioxatricyclo[6.3.0.02,6]undecan-1-ol
  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：

  1,2-O-isopropylidene-3-C-(prop-1-en-3-yl)-α-D-ribofuranose 在 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.5h， 生成 (3aR,5S,6S,6aR)-5-(iodomethyl)-2,2-dimethyl-6-prop-2-enyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-ol
  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

文献信息

• Strategies and tactics for free radical carbocyclization: synthesis of polyfunctionalized cyclopentanoid molecules from carbohydrates
  作者：José Marco-Contelles、Pilar Ruiz、Luis Martínez、Angeles Martínez-Grau

  DOI：10.1016/s0040-4020(01)81837-8

  日期：1993.7

  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.