2,5-dihydro-4-(4-chlorophenyl)-1,3-thiazino[5,6-b]indole | 1060654-30-9

• 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: 2,5-dihydro-4-(4-chlorophenyl)-1,3-thiazino[5,6-b]indole
• 英文别名: 4-(4-Chlorophenyl)-2,5-dihydro-[1,3]thiazino[5,6-b]indole
• CAS: 1060654-30-9
• 化学式: C₁₆H₁₁ClN₂S
• 分子量: 298.796
• InChiKey: FZLOBLYSYSXLBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-chlorothiobenzoylamino)methylthio-1H-indole 在 4-二甲氨基吡啶 、 碘甲烷 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以48%的产率得到2,5-dihydro-4-(4-chlorophenyl)-1,3-thiazino[5,6-b]indole
  参考文献：
  名称：

  Synthesis of 4-thiaharmalan analogue 4-aryl-1,3-thiazino[5,6-b]indole derivatives by prevention of rearrangements to position two of the indole moiety

  摘要：

  An efficient and selective non-acidic protocol has been developed for the synthesis of derivatives of a new ring system: 4-aryl-1,3-thiazino[5,6-b]indole, a 4-thiaharmalan analogue. The convenient amidomethylation of indole-3-thiol (5) afforded 3-beilzoylaminomethyithio-1H-indole (7a). with orthoamidomethylated 2-benzoylamino-methyl-3-benzoylaminomethylthio-1H-indole (8) as side product. Following the Bischler-Napieralski reaction of 7a the rearranged 2-benzoylaminomethylthio-1H-indole 11 could be isolated. In order to prevent such rearrangements the target thiazinoindoles were prepared via 3-thiobenzoylanlinomethylthioindole (13) via a modified Bischler-Napieralski reaction. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.014