ethyl 7-dimethylamino-2-methylthioindolizine-3-carboxylate | 140230-93-9

• 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: ethyl 7-dimethylamino-2-methylthioindolizine-3-carboxylate
• 英文别名: Ethyl 7-(dimethylamino)-2-methylsulfanylindolizine-3-carboxylate
• CAS: 140230-93-9
• 化学式: C₁₄H₁₈N₂O₂S
• 分子量: 278.375
• InChiKey: RJNBUZNQSOOIAJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  59.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7-dimethylamino-2-methylthioindolizine-3-carboxylate 在 镍 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 7-dimethylaminoindolizine
  参考文献：
  名称：

  Synthesis of a Luminescent Compound: 8-Dimethylaminopyridazino[4,5-a][2.2.3]cyclazine-1,4(2H,3H)-diones

  摘要：

  Some pyridazino[4,5-a][2.2.3]cyclazine-1,4(2H,3H)-diones (1a-d) as a luminescent compound were synthesized via several steps from indolizine derivatives. The key intermediates, dimethyl 6-dimethylamino[2.2.3]cyclazine-1,2-dicarboxylates (5, 7) were synthesized by the [8 + 2] cycloaddition reaction of 7-dimethylaminoindolizines (4, 6) with dimethyl acetylenedicarboxylate in the presence of Pd-C in refluxing toluene.

  DOI：

  10.3987/com-98-8249
• 作为产物：
  描述：

  1,1-双(甲硫基)-2-亚硝基乙烯 、 1-carbethoxymethyl-4-dimethylaminopyridinium bromide 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 ethyl 7-dimethylamino-2-methylthioindolizine-3-carboxylate 、 ethyl 7-dimethylamino-1-nitro-2-methylthioindolizine-3-carboxylate
  参考文献：
  名称：

  Synthesis of a Luminescent Compound: 8-Dimethylaminopyridazino[4,5-a][2.2.3]cyclazine-1,4(2H,3H)-diones

  摘要：

  Some pyridazino[4,5-a][2.2.3]cyclazine-1,4(2H,3H)-diones (1a-d) as a luminescent compound were synthesized via several steps from indolizine derivatives. The key intermediates, dimethyl 6-dimethylamino[2.2.3]cyclazine-1,2-dicarboxylates (5, 7) were synthesized by the [8 + 2] cycloaddition reaction of 7-dimethylaminoindolizines (4, 6) with dimethyl acetylenedicarboxylate in the presence of Pd-C in refluxing toluene.

  DOI：

  10.3987/com-98-8249

文献信息

• Synthesis of Bis(7-dimethylamino-1-indolizinyl)methane Derivatives and Their Oxidation: As an Oxidative Chromogenic Reagent in Clinical Analysis
  作者：Yoshinori Tominaga、Sachiko Itonaga、Tetsuya Kouno、Yasuhiro Shigemitsu

  DOI：10.3987/com-01-9260

  日期：——

  Acid-catalyzed condensation of 7-dimethylaminoindolizines with aldehydes led to substituted bis(7-dimethylaminoindolizin-1-yl)methanes (3a-i) which were easily converted into substituted bis(7-dimethylaminoindolizin-1-yl)methyl cations (4a-i) by oxidation with DDQ. These triaryl cation dyes were converted to the new heterocyclic ring system, 12-dimethylamino-6,8-bis(ethoxycarbonyl)-2H-thiopyrano[3,2-a:5,6-a']diindolizine-2-N,N-dimethyliminium perchlorates (5a, b), under reflux conditions in ethanol.