7-methyl-2,2-<(2R,4R)-2,4-pentanedioxy>-6-octen-1-ol | 152715-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-methyl-2,2-<(2R,4R)-2,4-pentanedioxy>-6-octen-1-ol
• CAS: 152715-83-8
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: KXJIWRWWQXEQAA-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  7-methyl-2,2-<(2R,4R)-2,4-pentanedioxy>-6-octen-1-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以73%的产率得到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：

  magnesium,2-methylpent-2-ene,bromide 在 吡啶 、 copper(l) iodide 、 sodium acetate 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 19.92h， 生成 7-methyl-2,2-<(2R,4R)-2,4-pentanedioxy>-6-octen-1-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