3-ethyl-2,4-dicyanoglutaramide | 145610-09-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-ethyl-2,4-dicyanoglutaramide
• 英文别名: 3-ethyl-2,4-dicyano-glutaric acid diamide；3-Aethyl-2,4-dicyan-glutarsaeure-diamid；2,4-Dicyano-3-ethylpentanediamide
• CAS: 145610-09-9
• 化学式: C₉H₁₂N₄O₂
• 分子量: 208.22
• InChiKey: SKZZRGWYEGOUAN-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  564.9±50.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethyl-2,4-dicyanoglutaramide 在 盐酸 、 乙酸酐 作用下， 反应 16.0h， 生成 3-乙基戊二酸酐
  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：

  丙醛 、 氰乙酰胺 在 哌啶 作用下， 以 水 为溶剂， 以85%的产率得到3-ethyl-2,4-dicyanoglutaramide
  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

• Day; Thorpe, Journal of the Chemical Society, 1920, vol. 117, p. 1472
  作者：Day、Thorpe

  DOI：——

  日期：——
• Jeffery; Vogel, Journal of the Chemical Society, 1939, p. 449
  作者：Jeffery、Vogel

  DOI：——

  日期：——
• Theisen Peter D., Heathcock Clayton H., J. Org. Chem., 58 (1993) N 1, S 142-146
  作者：Theisen Peter D., Heathcock Clayton H.

  DOI：——

  日期：——
• 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.