3,3-Bis-ethoxycarbonyl-hexanedioic acid 1-ethyl ester 6-methyl ester | 136547-09-6

• 英文名称: 3,3-Bis-ethoxycarbonyl-hexanedioic acid 1-ethyl ester 6-methyl ester
• CAS: 136547-09-6
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: GIUFNWSLKIVYSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,3-Bis-ethoxycarbonyl-hexanedioic acid 1-ethyl ester 6-methyl ester 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以83%的产率得到1,2,4-丁三羧酸,1,2-二乙基4-甲基酯
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357
• 作为产物：
  描述：

  丙二酸二乙酯 在 苄基三乙基氯化铵 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,3-Bis-ethoxycarbonyl-hexanedioic acid 1-ethyl ester 6-methyl ester
  参考文献：
  名称：

  Synthesis of polyfunctional aliphatic carbonyl compounds under phase-transfer conditions

  摘要：

  We have studied mono- and dialkylation of malonic, acetoacetic, and cyanoacetic esters with esters of haloacetic and beta-halopropionic acids and addition of the CH acids mentioned and their analogs to methyl and ethyl acrylate under phase-transfer catalysis conditions, and also deethoxycarbonylation of the obtained products. We have demonstrated for the first time the possibility of Dieckmann cyclization under phase-transfer catalysis conditions and have developed a simple method for the synthesis of 2,3-di(ethoxycarbonyl)cyclopentanone, a key intermediate in the syntheis of deoxyprostaglandins, by cyclization of triethyl 1,2,4-butanetricarboxylate.

  DOI：

  10.1007/bf00961357