(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate | 1542432-73-4

• 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: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate
• CAS: 1542432-73-4
• 化学式: C₁₆H₂₅F₆O₅P
• 分子量: 442.336
• InChiKey: KELCYPXOVIKMIB-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  反式肉桂醛 、 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate 在 哌啶鎓苯甲酸盐 作用下， 以 苯 为溶剂， 反应 5.0h， 以40%的产率得到
  参考文献：
  名称：

  Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels–Alder dimerization of a [3]dendralene attached to a (−)-menthol auxiliary

  摘要：

  A novel route to a chiral functionalized [3]dendralene attached to a (-)-menthol auxiliary has been developed, which involves a dimethylsulfonium methylide mediated olefination of a substituted ethenylidene phosphonoacetate (-)-menthyl ester, followed by a Horner-Wordsworth-Emmons reaction with 4-bromobenzaldehyde. The chiral [3]dendralene was reactive enough to undergo intermolecular Diels-Alder cyclodimerization to give the highly substituted cyclohexene with very high regio- and diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.005
• 作为产物：
  描述：

  (1R,2S,5R)-menthol bromoacetate 在 五氯化磷 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 21.08h， 生成 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]acetate
  参考文献：
  名称：

  Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels–Alder dimerization of a [3]dendralene attached to a (−)-menthol auxiliary

  摘要：

  A novel route to a chiral functionalized [3]dendralene attached to a (-)-menthol auxiliary has been developed, which involves a dimethylsulfonium methylide mediated olefination of a substituted ethenylidene phosphonoacetate (-)-menthyl ester, followed by a Horner-Wordsworth-Emmons reaction with 4-bromobenzaldehyde. The chiral [3]dendralene was reactive enough to undergo intermolecular Diels-Alder cyclodimerization to give the highly substituted cyclohexene with very high regio- and diastereoselectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.11.005