(2E,4E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate | 1542432-75-6

• 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: (2E,4E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2E,4E)-2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate
• CAS: 1542432-75-6
• 化学式: C₂₅H₃₁F₆O₅P
• 分子量: 556.482
• InChiKey: CZIWXDVPBLOJAP-RZKCTRGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(diethoxyphosphoryl)acetate 在 五氯化磷 、 哌啶鎓苯甲酸盐 、 N,N-二异丙基乙胺 作用下， 以 苯 为溶剂， 反应 23.08h， 生成 (2E,4E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate 、 (2Z,4E)-(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-[bis(2,2,2-trifluoroethoxy)phosphoryl]-5-phenylpenta-2,4-dienoate
  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

文献信息

• 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
  作者：Rekha Singh、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2013.11.005

  日期：2014.1

  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.