diethyl 2-acetyl-2-(2-formylethyl)glutarate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: diethyl 2-acetyl-2-(2-formylethyl)glutarate
• 英文别名: Diethyl 2-acetyl-2-(3-oxopropyl)pentanedioate
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: OSPXOHVLWCFTIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-acetyl-2-(2-formylethyl)glutarate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以33%的产率得到ethyl 3-(1-ethoxycarbonyl-2-oxocyclohex-3-en-1-yl)propionate
  参考文献：
  名称：

  Syntheses of the terpenoid precursors cyclopent-2-enone and cyclohex-2-enone diesters

  摘要：

  Two reaction pathways were elaborated for the practical and convenient synthesis of the title compounds: The first route applies a bromination-dehydrobromination sequence to introduce the double bond into 1-alkoxycarbonyl-2-oxocycloalkylacetic and propionic esters (4a-c, 7a,b). The application of 2,6-lutidine for dehydrobromination of alpha-bromocycloalkanones diesters (5a-c, 8a, b) provides sufficient selectivity to carry out this step without affecting the sensitive ester group. Alternative pathways, involving Michael reaction of diethyl 2-acetylsuccinate or -glutarate with acrolein and subsequent intramolecular aldol condensation, are presented in the case of cyclohex-2-enone derivatives 2a, b.

  DOI：

  10.1007/bf00811764
• 作为产物：
  描述：

  乙酰戊二酸二乙酯 、 丙烯醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以69%的产率得到diethyl 2-acetyl-2-(2-formylethyl)glutarate
  参考文献：
  名称：

  Syntheses of the terpenoid precursors cyclopent-2-enone and cyclohex-2-enone diesters

  摘要：

  Two reaction pathways were elaborated for the practical and convenient synthesis of the title compounds: The first route applies a bromination-dehydrobromination sequence to introduce the double bond into 1-alkoxycarbonyl-2-oxocycloalkylacetic and propionic esters (4a-c, 7a,b). The application of 2,6-lutidine for dehydrobromination of alpha-bromocycloalkanones diesters (5a-c, 8a, b) provides sufficient selectivity to carry out this step without affecting the sensitive ester group. Alternative pathways, involving Michael reaction of diethyl 2-acetylsuccinate or -glutarate with acrolein and subsequent intramolecular aldol condensation, are presented in the case of cyclohex-2-enone derivatives 2a, b.

  DOI：

  10.1007/bf00811764

文献信息

• Syntheses of the terpenoid precursors cyclopent-2-enone and cyclohex-2-enone diesters
  作者：I. Kádas、V. Morvai、G. Árvai、L. Tőke、Á. Szöllősy、G. Tóth、M. Bihari

  DOI：10.1007/bf00811764

  日期：1995.1

  Two reaction pathways were elaborated for the practical and convenient synthesis of the title compounds: The first route applies a bromination-dehydrobromination sequence to introduce the double bond into 1-alkoxycarbonyl-2-oxocycloalkylacetic and propionic esters (4a-c, 7a,b). The application of 2,6-lutidine for dehydrobromination of alpha-bromocycloalkanones diesters (5a-c, 8a, b) provides sufficient selectivity to carry out this step without affecting the sensitive ester group. Alternative pathways, involving Michael reaction of diethyl 2-acetylsuccinate or -glutarate with acrolein and subsequent intramolecular aldol condensation, are presented in the case of cyclohex-2-enone derivatives 2a, b.