1-hydroxy-7-methyl-6-octen-2-one | 152715-80-5

• 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: 1-hydroxy-7-methyl-6-octen-2-one
• CAS: 152715-80-5
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: TWWXSAHFNOCKAU-UHFFFAOYSA-N

物化性质

• 沸点：
  247.3±23.0 °C(predicted)
• 密度：
  0.945±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-7-methyl-6-octen-2-one 在 吡啶 、 草酰氯 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 11.5h， 生成 7-methyl-2,2-<(2R,4R)-2,4-pentanedioxy>-6-octen-1-al
  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：

  7-methyl-1-trityloxy-6-octen-2-one 在 溶剂黄146 作用下， 反应 1.5h， 以63%的产率得到1-hydroxy-7-methyl-6-octen-2-one
  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