2-[(1R,2S,5R)-1-((S)-2-Hydroxy-2-hydroxymethyl-pent-4-enyloxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone | 138489-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(1R,2S,5R)-1-((S)-2-Hydroxy-2-hydroxymethyl-pent-4-enyloxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone
• CAS: 138489-65-3
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: IENRGSDLLSFONC-BKXMBWNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[(1R,2S,5R)-1-((S)-2-Hydroxy-2-hydroxymethyl-pent-4-enyloxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 在 D(+)-10-樟脑磺酸 、 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 2.5h， 生成 (R)-2,2-Dimethyl-4-(2-propenyl)-1,3-dioxolane-4-methanol
  参考文献：
  名称：

  A general method for the preparation of enantiomerically pure 2-substituted glycerol derivatives by utilizing l-menthone as a chiral template

  摘要：

  A general method for preparation of a variety of enantiomerically pure 2-substituted glycerol derivatives 1 was developed by utilizing l-menthone as a chiral template. Spiroacetals 6 derived formally from 2-substituted 2-(trimethylsiloxy)-1,3-propanediols and l-menthone were prepared with high stereoselectivity (> 95% de) either by Grignard reactions of oxospiroacetal 4 or by epoxidation of methylenespiroacetal 5 followed by ring opening with higher order cuprates. Highly stereoselective ring-cleavage reaction of 6 with acetophenone enol trimethylsilyl ether and TiCl4 followed by protection of the resulting diol 10 and subsequent removal of the chiral auxiliary gave 2-substituted glycerol derivatives of high enantiomeric purity.

  DOI：

  10.1021/jo00028a057
• 作为产物：
  描述：

  (8R,11S)-8-methyl-3-methylidene-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane 在 三氟甲磺酸三甲基硅酯 、 四氯化钛 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 30.0h， 生成 2-[(1R,2S,5R)-1-((S)-2-Hydroxy-2-hydroxymethyl-pent-4-enyloxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone
  参考文献：
  名称：

  A general method for the preparation of enantiomerically pure 2-substituted glycerol derivatives by utilizing l-menthone as a chiral template

  摘要：

  A general method for preparation of a variety of enantiomerically pure 2-substituted glycerol derivatives 1 was developed by utilizing l-menthone as a chiral template. Spiroacetals 6 derived formally from 2-substituted 2-(trimethylsiloxy)-1,3-propanediols and l-menthone were prepared with high stereoselectivity (> 95% de) either by Grignard reactions of oxospiroacetal 4 or by epoxidation of methylenespiroacetal 5 followed by ring opening with higher order cuprates. Highly stereoselective ring-cleavage reaction of 6 with acetophenone enol trimethylsilyl ether and TiCl4 followed by protection of the resulting diol 10 and subsequent removal of the chiral auxiliary gave 2-substituted glycerol derivatives of high enantiomeric purity.

  DOI：

  10.1021/jo00028a057