10,11-dihydro-10-methyl-12H-indolo[3,2-b][1,5]benzothiazepin-11-one | 1000069-77-1

• 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: 10,11-dihydro-10-methyl-12H-indolo[3,2-b][1,5]benzothiazepin-11-one
• 英文别名: 7-methyl-5H-indolo[3,2-b][1,5]benzothiazepin-6-one
• CAS: 1000069-77-1
• 化学式: C₁₆H₁₂N₂OS
• 分子量: 280.35
• InChiKey: INUHDOOPSCXTHU-UHFFFAOYSA-N

物化性质

• 熔点：
  290 °C (decomp)
• 沸点：
  529.2±42.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10,11-dihydro-10-methyl-12H-indolo[3,2-b][1,5]benzothiazepin-11-one 、 碘甲烷 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 以76%的产率得到10,11-dihydro-10,12-dimethyl-12H-indolo[3,2-b][1,5]benzothiazepin-11-one
  参考文献：
  名称：

  Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides

  摘要：

  When N-[2-(alkylsulfinyl)phenyl]-1 H-indole-2-carboxamides with varying degrees of indolic and amidic N-alkylation are heated in an inert solvent or treated with trifluoroacetic anhydride; only compounds in which the amidic nitrogen is methylated cyclize to indolo[3,2b]- 1,5-benzothiazepinones (9, 10). Successful cyclization is attributed to the ability of N-Me amides to readily adopt a conformation conducive to cyclization, which other derivatives are unable to achieve. The analogous 3-indoleanilide, N,N-dimethyl N-[2-(ethylsulfnyl)phenyl]- I H-indole-3-carboxamide (17a), undergoes SES/rearrangement to produce 10 upon heating in p-xylene. An intermediate 3H-indolinium spirocyclic species is proposed to account for this result. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.050
• 作为产物：
  描述：

  Ethyl-o-(methylamino)phenylsulfid 在 吡啶 、 三氟乙酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 10,11-dihydro-10-methyl-12H-indolo[3,2-b][1,5]benzothiazepin-11-one
  参考文献：
  名称：

  Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides

  摘要：

  When N-[2-(alkylsulfinyl)phenyl]-1 H-indole-2-carboxamides with varying degrees of indolic and amidic N-alkylation are heated in an inert solvent or treated with trifluoroacetic anhydride; only compounds in which the amidic nitrogen is methylated cyclize to indolo[3,2b]- 1,5-benzothiazepinones (9, 10). Successful cyclization is attributed to the ability of N-Me amides to readily adopt a conformation conducive to cyclization, which other derivatives are unable to achieve. The analogous 3-indoleanilide, N,N-dimethyl N-[2-(ethylsulfnyl)phenyl]- I H-indole-3-carboxamide (17a), undergoes SES/rearrangement to produce 10 upon heating in p-xylene. An intermediate 3H-indolinium spirocyclic species is proposed to account for this result. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.050