(3S)-3-methyl-5-[(1S)-1-naphthalen-1-ylethoxy]-5-oxopentanoic acid | 218304-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3S)-3-methyl-5-[(1S)-1-naphthalen-1-ylethoxy]-5-oxopentanoic acid
• CAS: 218304-92-8
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: XEYVXDIDNSICEP-STQMWFEESA-N

物化性质

• 沸点：
  479.0±28.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-methyl-5-[(1S)-1-naphthalen-1-ylethoxy]-5-oxopentanoic acid 在 palladium on activated charcoal dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 methyl 3-(R)-methyl-5-hydroxypentanoate
  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
• 作为产物：
  描述：

  3-甲基戊二酸酐 、 (S)-(-)-1-萘基-1-乙醇 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (3S)-3-methyl-5-[(1S)-1-naphthalen-1-ylethoxy]-5-oxopentanoic acid
  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

• Tributylphosphine-catalyzed acylations of alcohols: scope and related reactions
  作者：E. Vedejs、N. S. Bennett、L. M. Conn、S. T. Diver、M. Gingras、S. Lin、P. A. Oliver、M. J. Peterson

  DOI：10.1021/jo00077a064

  日期：1993.12
• 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.