dimethyl 1-(methylene)thiopyrano[2,3-b]indole-2,3-dicarboxylate | 518329-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: dimethyl 1-(methylene)thiopyrano[2,3-b]indole-2,3-dicarboxylate
• 英文别名: Dimethyl 9-methyl-4-methylidenethiopyrano[2,3-b]indole-2,3-dicarboxylate
• CAS: 518329-62-9
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: SMBGRLJKOIGZTO-UHFFFAOYSA-N

物化性质

• 沸点：
  507.2±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 1-(methylene)thiopyrano[2,3-b]indole-2,3-dicarboxylate 以 甲醇 为溶剂， 生成 dimethyl (4E)-4-[(2E)-2-[2,3-bis(methoxycarbonyl)-9-methylthiopyrano[2,3-b]indol-4-ylidene]ethylidene]-9-methylthiopyrano[2,3-b]indole-2,3-dicarboxylate
  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
• 作为产物：
  描述：

  1,5-dimethyl-2,3-bis(methoxycarbonyl)indolo[2,3-b]thiopyrylium perchlorate 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以94%的产率得到dimethyl 1-(methylene)thiopyrano[2,3-b]indole-2,3-dicarboxylate
  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

文献信息

• Synthesis of New Thiopyrylocyanines Incorporated Thiopyrano[2,3-b]indole Ring as the Main Constituent
  作者：Yoshinori Tominaga、Yasuhiro Shigemitsu、Shun-ichi Hirayama

  DOI：10.3987/com-02-9612

  日期：——

  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.