(2R,4R,7S,8R)-8-Isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol | 152715-71-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,4R,7S,8R)-8-Isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol
• CAS: 152715-71-4
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: ODPHEOYSEDRUSU-LPWJVIDDSA-N

物化性质

• 沸点：
  346.8±27.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,7S,8R)-8-Isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Acetic acid (1S,2R)-2-isopropyl-6-oxo-cyclohexyl ester
  参考文献：
  名称：

  Insight into Rh(I)-catalyzed cyclization of 6-octen-1-als with a chiral protecting group

  摘要：

  Rh(I)(Wilkinson )[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-1-als with a chiral protecting group at the C2-position afforded only cis-cyclohexanol derivatives, and in the case of C4-position yielded a mixture of cis and trans cyclohexanol. These findings were remarkably different from the case of the C3-position, in which the trans cyclohexanol derivative was obtained. Wilkinson's complex acts as [ClRh(PPh3)3] a Lewis acid, and this bulkier Lewis acid affords higher diastereoselectivity. Rh(I)-catalyzed cyclization of 6-octen-1-al derivatives is not affected by chiral ligands.

  DOI：

  10.1016/s0957-4166(00)80426-7
• 作为产物：
  描述：

  (2R,4R,7S,8R)-8-Isopropenyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到(2R,4R,7S,8R)-8-Isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol
  参考文献：
  名称：

  Insight into Rh(I)-catalyzed cyclization of 6-octen-1-als with a chiral protecting group

  摘要：

  Rh(I)(Wilkinson )[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-1-als with a chiral protecting group at the C2-position afforded only cis-cyclohexanol derivatives, and in the case of C4-position yielded a mixture of cis and trans cyclohexanol. These findings were remarkably different from the case of the C3-position, in which the trans cyclohexanol derivative was obtained. Wilkinson's complex acts as [ClRh(PPh3)3] a Lewis acid, and this bulkier Lewis acid affords higher diastereoselectivity. Rh(I)-catalyzed cyclization of 6-octen-1-al derivatives is not affected by chiral ligands.

  DOI：

  10.1016/s0957-4166(00)80426-7