(1'SR,3RS)-1-(1'-naphthyl)ethyl methyl 3-ethylpentanedioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1'SR,3RS)-1-(1'-naphthyl)ethyl methyl 3-ethylpentanedioate
• 英文别名: 1-O-methyl 5-O-[(1S)-1-naphthalen-1-ylethyl] (3R)-3-ethylpentanedioate
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: BOVUOGVCODVZNO-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙基戊二酸酐 在 4-二甲氨基吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (1'SR,3RS)-1-(1'-naphthyl)ethyl methyl 3-ethylpentanedioate
  参考文献：
  名称：

  Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols

  摘要：

  The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated. Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtain the corresponding diesters 16-20. The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, with the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively. The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.

  DOI：

  10.1021/jo00053a027

文献信息

• Prochiral recognition in the reaction of 3-substituted glutaric anhydrides with chiral secondary alcohols
  作者：Peter D. Theisen、Clayton H. Heathcock

  DOI：10.1021/jo00053a027

  日期：1993.1

  The scope of a previously-reported process for the desymmetrization 3-substituted glutaric anhydrides has been investigated. Thus, prochiral anhydrides 5-9 react with 1-(1'-naphthyl)ethanol (2) to give glutaric acid half-esters, which are esterified by treatment with diazomethane to obtain the corresponding diesters 16-20. The degree of prochiral recognition is inversely related to the steric bulk of the stereodifferentiating group, with the series TBDMSO, Me, Et, Ph, i-Pr, and t-Bu giving ratios of 40:1, 16:1, 14:1, 8:1, 7:1, and 1:3, respectively. The absolute sense of the prochiral recognition was established by conversion of two of the diesters, 16a and 18a, into 3-substituted valerolactones (22a, 22c) of known absolute configuration.