1-acetyl-2,3-dimethyl-2,3-dihydro-indole | 31768-04-4

• 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: 1-acetyl-2,3-dimethyl-2,3-dihydro-indole
• 英文别名: N-Acetyl-2,3-dimethyl-2,3-dihydroindol；1-Acetyl-2,3-dimethylindoline；1-(2,3-dimethyl-2,3-dihydroindol-1-yl)ethanone
• CAS: 31768-04-4
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: BOWUEFKWRRCZBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-acetyl-2,3-dimethyl-2,3-dihydro-indole 在 铂 硫酸 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 生成 1-Acetyl-2,3,6,7-tetramethyl-1,2,3,5-tetrahydropyrrolo[2,3-f]indole
  参考文献：
  名称：

  Regioselectivity in electrophilic substitution of 5-aminoindoles and 5-aminoindolines: synthesis of pyrrolo[3,2-e]indoles and isomeric pyrrolo[2,3-f]indoles

  摘要：

  An FMO Theory prediction that 5-aminoindoles, 5, should react with electrophiles preferentially at C4 rather than at C6 whereas N1-acyl-5-aminoindolines, 6, should react preferentially at C6 rather than C4 is borne out experimentally by the synthesis of a pyrrolo[3,2-e]indole from 5 and pyrrolo[2,3-f]indoles from 6.

  DOI：

  10.1016/s0040-4039(00)93421-x
• 作为产物：
  描述：

  2，3-二甲基吲哚 、 乙酸酐 在 对甲苯磺酸 作用下， 生成 1-acetyl-2,3-dimethyl-2,3-dihydro-indole
  参考文献：
  名称：

  Regioselectivity in electrophilic substitution of 5-aminoindoles and 5-aminoindolines: synthesis of pyrrolo[3,2-e]indoles and isomeric pyrrolo[2,3-f]indoles

  摘要：

  An FMO Theory prediction that 5-aminoindoles, 5, should react with electrophiles preferentially at C4 rather than at C6 whereas N1-acyl-5-aminoindolines, 6, should react preferentially at C6 rather than C4 is borne out experimentally by the synthesis of a pyrrolo[3,2-e]indole from 5 and pyrrolo[2,3-f]indoles from 6.

  DOI：

  10.1016/s0040-4039(00)93421-x

文献信息

• Rhodium-catalyzed C7-alkylation of indolines with maleimides
  作者：Changduo Pan、Yun Wang、Chao Wu、Jin-Tao Yu

  DOI：10.1039/c7ob03039h

  日期：——

  A rhodium(III)-catalyzed direct cross-coupling reaction of indolines with maleimides via C–H bond activation was developed. This protocol displays good functional group tolerance, which offers a novel approach to access C7 modified indoline derivatives including maleimide analogues.

  开发了铑（III）催化的吲哚啉与马来酰亚胺通过C–H键活化的直接交叉偶联反应。该协议显示出良好的官能团耐受性，这为获得包括马来酰亚胺类似物的C7修饰的吲哚衍生物提供了一种新颖的方法。
• KOST A. N.; YUDIN L. G.; ABDULLAEV M., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 10, 1339-1342
  作者：KOST A. N.、 YUDIN L. G.、 ABDULLAEV M.

  DOI：——

  日期：——
• Peptides containing an aliphatic-aromatic ketone side chain
  申请人：THE SALK INSTITUTE FOR BIOLOGICAL STUDIES

  公开号：EP0192492B1

  公开（公告）日：1992-01-02
• Regioselectivity in electrophilic substitution of 5-aminoindoles and 5-aminoindolines: synthesis of pyrrolo[3,2-e]indoles and isomeric pyrrolo[2,3-f]indoles
  作者：Ganesh K.B. Prasad、Andrew Burchat、Gamini Weeratunga、Ian Watts、Gary I. Dmitrienko

  DOI：10.1016/s0040-4039(00)93421-x

  日期：1991.9

  An FMO Theory prediction that 5-aminoindoles, 5, should react with electrophiles preferentially at C4 rather than at C6 whereas N1-acyl-5-aminoindolines, 6, should react preferentially at C6 rather than C4 is borne out experimentally by the synthesis of a pyrrolo[3,2-e]indole from 5 and pyrrolo[2,3-f]indoles from 6.