dimethyl 1-(methyl)thiopyrano[2,3-b]indole-2,3-dicarboxylate hydrochloride | 51544-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethyl 1-(methyl)thiopyrano[2,3-b]indole-2,3-dicarboxylate hydrochloride
• 英文别名: 2,3-bis-methoxycarbonyl-4-methyl-9H-thiopyrano[2,3-b]indolium; chloride
• CAS: 51544-39-9
• 化学式: C₁₆H₁₃NO₄S*ClH
• 分子量: 351.81
• InChiKey: REVVPVFLKQWFHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.49
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl 2-methylindole-3-dithiocarboxylate 在 盐酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 dimethyl 1-(methyl)thiopyrano[2,3-b]indole-2,3-dicarboxylate hydrochloride
  参考文献：
  名称：

  Synthesis of New Thiopyrylocyanines Incorporated Thiopyrano[2,3-b]indole Ring as the Main Constituent

  摘要：

  The Diels-Alder product, dimethyl 5-methyl-4a-methyl-1-methylthiothiopyrano[4,3-b] indole-3,4-dicarboxylate (2b), which was obtained by the reaction of methyl 1,2-dimethylindole-3 -dithiocarboxylate (1b) with DMAD (dimethyl acetylenedicarboxylate), was easily converted to a 1,5-dimethyl-2,3-bis(methoxycarbonyl)indolo[2,3-b]thiopyrylium perchlorate (5) as the key intermediate for the thiopyrylocyanine and merocyanine dyes. Compounds (5 and 6) were allowed to react with aromatic aldehydes and some electrophilic reagents to yield cyanine and merocyanine dyes (8a-c, 10-12) in good yields.

  DOI：

  10.3987/com-02-9612