dimethyl 3-(3-coumarinylcarbonyl)-6,8-dimethylindolizine-1,2-dicarboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: dimethyl 3-(3-coumarinylcarbonyl)-6,8-dimethylindolizine-1,2-dicarboxylate
• 英文别名: Dimethyl 6,8-dimethyl-3-(2-oxochromene-3-carbonyl)indolizine-1,2-dicarboxylate
• 化学式: C₂₄H₁₉NO₇
• 分子量: 433.417
• InChiKey: ONSXXMZNSIKQFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,5-二甲基吡啶 在 哌啶 、 四氯苯醌 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 39.33h， 生成 dimethyl 3-(3-coumarinylcarbonyl)-6,8-dimethylindolizine-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.