ethyl 3-bromo-1-ethoxycarbonyl-2-oxocyclopent-1-ylacetate | 58308-83-1

• 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: ethyl 3-bromo-1-ethoxycarbonyl-2-oxocyclopent-1-ylacetate
• 英文别名: Ethyl 3-bromo-1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentane-1-carboxylate
• CAS: 58308-83-1
• 化学式: C₁₂H₁₇BrO₅
• 分子量: 321.168
• InChiKey: HQWXHMGWYJSNSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-bromo-1-ethoxycarbonyl-2-oxocyclopent-1-ylacetate 在 2,6-二甲基吡啶 作用下， 反应 9.0h， 以61.8%的产率得到ethyl 1-ethoxycarbonyl-2-oxocyclopent-3-en-1-ylacetate
  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：

  1-乙氧基羰基甲基-2-氧代-环戊烷羧酸乙酯 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到ethyl 3-bromo-1-ethoxycarbonyl-2-oxocyclopent-1-ylacetate
  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.