Acetic acid (2R,4R,7R,8S)-8-isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undec-7-yl ester | 152785-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,4R,7R,8S)-8-isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undec-7-yl ester
• CAS: 152785-52-9
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: KMADYVGBPUVCAH-RJZRQDKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,4R,7R,8S)-8-isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undec-7-yl ester 在 溶剂黄146 作用下， 反应 1.0h， 以92%的产率得到Acetic acid (1R,2S)-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,7R,8S)-8-Isopropenyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,4R,7R,8S)-8-isopropyl-2,4-dimethyl-1,5-dioxa-spiro[5.5]undec-7-yl 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