dimethyl 4a,5-dimethyl-1-(methylthio)thiopyrano[4,3-b]indole-3,4-dicarboxylate | 51544-30-0

• 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 4a,5-dimethyl-1-(methylthio)thiopyrano[4,3-b]indole-3,4-dicarboxylate
• 英文别名: 4a,5-dimethyl-1-methylsulfanyl-4a,5-dihydro-thiopyrano[4,3-b]indole-3,4-dicarboxylic acid dimethyl ester；Dimethyl 4a,5-dimethyl-1-methylsulfanylthiopyrano[4,3-b]indole-3,4-dicarboxylate
• CAS: 51544-30-0
• 化学式: C₁₈H₁₉NO₄S₂
• 分子量: 377.485
• InChiKey: UFVJIKKLXILZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 4a,5-dimethyl-1-(methylthio)thiopyrano[4,3-b]indole-3,4-dicarboxylate 在 盐酸 作用下， 以 甲醇 为溶剂， 以66%的产率得到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：

  methyl 1,2-dimethylindole-3-dithiocarboxylate 、 丁炔二酸二甲酯 以 1,4-二氧六环 为溶剂， 生成 dimethyl 4a,5-dimethyl-1-(methylthio)thiopyrano[4,3-b]indole-3,4-dicarboxylate
  参考文献：
  名称：

  Studies on Indole Derivatives. XXIII. Diels-Alder Reaction of 3-Indoledithiocarboxylic Acid Derivatives and Dimethyl Acetylenedicarboxylate and Reactions of Their Products

  摘要：

  DOI：

  10.1248/cpb.21.2770

文献信息

• Studies on Indole Derivatives. XXIII. Diels-Alder Reaction of 3-Indoledithiocarboxylic Acid Derivatives and Dimethyl Acetylenedicarboxylate and Reactions of Their Products
  作者：YOSHINORI TOMINAGA、REIKO NATSUKI、YOSHIRO MATSUDA、GORO KOBAYASHI

  DOI：10.1248/cpb.21.2770

  日期：——
• 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.