dimethyl 3-(ethoxycarbonylacetyl)indolizine-1,2-dicarboxylate | 333360-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: dimethyl 3-(ethoxycarbonylacetyl)indolizine-1,2-dicarboxylate
• 英文别名: Dimethyl 3-(3-ethoxy-3-oxopropanoyl)indolizine-1,2-dicarboxylate
• CAS: 333360-94-4
• 化学式: C₁₇H₁₇NO₇
• 分子量: 347.324
• InChiKey: AJBBSXDYLJEUMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  邻甲基苄醇 、 dimethyl 3-(ethoxycarbonylacetyl)indolizine-1,2-dicarboxylate 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以73%的产率得到dimethyl 3-(2H-2-oxo-chromen-3-yl)carbonylindolizine-1,2-dicarboxylate
  参考文献：
  名称：

  Preparation of New Nitrogen-bridged Heterocycles. 50.1 Syntheses of Some Heterocyclic Compounds Starting from Pyridinium 1-(Ethoxycarbonylacetyl)methylides

  摘要：

  The reactions of the title methylides with dialkyl acetylenedicarboxylates gave the corresponding 3-(ethoxycarbonylacetyl)-indolizine derivatives, whose 3-substituent was smoothly converted to a coumarin skeleton by Knoevenagel reaction with salicylaldehyde. The reactions of the methylides with carbon disulfide and alkylating agent in the presence of a base afforded pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides, and the S-alkylations of these ylides with phenacyl bromides and subsequent alkaline treatment of the resulting pyridinium salts gave ethyl 3-alkylthio-1-(arylcarbonyl)thieno[3,4-b]indolizine-9-carboxylates.

  DOI：

  10.3987/com-00-s(i)15
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 在 四氯苯醌 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 39.0h， 生成 dimethyl 3-(ethoxycarbonylacetyl)indolizine-1,2-dicarboxylate
  参考文献：
  名称：

  Preparation of New Nitrogen-bridged Heterocycles. 50.1 Syntheses of Some Heterocyclic Compounds Starting from Pyridinium 1-(Ethoxycarbonylacetyl)methylides

  摘要：

  The reactions of the title methylides with dialkyl acetylenedicarboxylates gave the corresponding 3-(ethoxycarbonylacetyl)-indolizine derivatives, whose 3-substituent was smoothly converted to a coumarin skeleton by Knoevenagel reaction with salicylaldehyde. The reactions of the methylides with carbon disulfide and alkylating agent in the presence of a base afforded pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides, and the S-alkylations of these ylides with phenacyl bromides and subsequent alkaline treatment of the resulting pyridinium salts gave ethyl 3-alkylthio-1-(arylcarbonyl)thieno[3,4-b]indolizine-9-carboxylates.

  DOI：

  10.3987/com-00-s(i)15

文献信息

• Preparation of New Nitrogen-bridged Heterocycles. 50.1 Syntheses of Some Heterocyclic Compounds Starting from Pyridinium 1-(Ethoxycarbonylacetyl)methylides
  作者：Akikazu Kakehi、Suketaka Ito、Hiroyuki Suga、Katsuaki Yasuraoka

  DOI：10.3987/com-00-s(i)15

  日期：——

  The reactions of the title methylides with dialkyl acetylenedicarboxylates gave the corresponding 3-(ethoxycarbonylacetyl)-indolizine derivatives, whose 3-substituent was smoothly converted to a coumarin skeleton by Knoevenagel reaction with salicylaldehyde. The reactions of the methylides with carbon disulfide and alkylating agent in the presence of a base afforded pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides, and the S-alkylations of these ylides with phenacyl bromides and subsequent alkaline treatment of the resulting pyridinium salts gave ethyl 3-alkylthio-1-(arylcarbonyl)thieno[3,4-b]indolizine-9-carboxylates.