3,3-bis-methoxycarbonyl-hex-5-enoic acid methyl ester | 887946-73-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,3-bis-methoxycarbonyl-hex-5-enoic acid methyl ester
• 英文别名: Trimethyl pent-4-ene-1,2,2-tricarboxylate；trimethyl pent-4-ene-1,2,2-tricarboxylate
• CAS: 887946-73-8
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: LWXDZDZJUGZGTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-bis-methoxycarbonyl-hex-5-enoic acid methyl ester 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1,4,9,9a-tetrahydro-1H-cyclopenta[b]quinoline-2,2,3-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines

  摘要：

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

  DOI：

  10.1021/ol0604421
• 作为产物：
  描述：

  丙二酸二甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成 3,3-bis-methoxycarbonyl-hex-5-enoic acid methyl ester
  参考文献：
  名称：

  Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines

  摘要：

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.

  DOI：

  10.1021/ol0604421

文献信息

• US4428887A
  申请人：——

  公开号：US4428887A

  公开（公告）日：1984-01-31
• Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines
  作者：Birgit Janza、Armido Studer

  DOI：10.1021/ol0604421

  日期：2006.4.1

  An efficient tandem radical process comprising a thermal alkoxyamine homolysis, an isonitrile trapping reaction, a 5-exo-trig cyclization, and a homolytic aromatic substitution leads to substituted dihydroquinolines. Depending on the substituent R-1, oxidation to dihydro-1H-cyclopenta[b]quinolines (for R-1 = aryl) or tautomerization to tetrahydro-1H-cyclopenta[b]quinolines (for R-1 = CO2Me, CN) occurs. The heterocycles are obtained in moderate to good yields. Upon using microwave-induced heating, the reaction time can be shortened from 3 days to 30 min.