N-[2-(tert-butylthio)phenyl]-N-methyl-1H-indole-2-carboxamide | 1000069-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(tert-butylthio)phenyl]-N-methyl-1H-indole-2-carboxamide
• 英文别名: N-(2-tert-butylsulfanylphenyl)-N-methyl-1H-indole-2-carboxamide
• CAS: 1000069-64-6
• 化学式: C₂₀H₂₂N₂OS
• 分子量: 338.473
• InChiKey: GVXMBXWOAXUMBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  N-[2-(tert-butylthio)phenyl]-N-methyl-1H-indole-2-carboxamide 在 吡啶 、 间氯过氧苯甲酸 、 三氟乙酸酐 作用下， 以 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
• 作为产物：
  描述：

  2-叔丁硫基苯胺 在 盐酸 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 185.0h， 生成 N-[2-(tert-butylthio)phenyl]-N-methyl-1H-indole-2-carboxamide
  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

文献信息

• Intramolecular sulfoxide electrophilic sulfenylation in 2- and 3-indoleanilides
  作者：Mary E. Eggers、Parag V. Jog、Dallas K. Bates

  DOI：10.1016/j.tet.2007.09.050

  日期：2007.12

  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.