1-benzyl-3-(2,2-dimethylpropyl)-5-methyl-1H-indole

• 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-benzyl-3-(2,2-dimethylpropyl)-5-methyl-1H-indole
• 英文别名: 1-Benzyl-3-(2,2-dimethylpropyl)-5-methylindole
• 化学式: C₂₁H₂₅N
• 分子量: 291.436
• InChiKey: IVHLTERBKLQQJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 四(三苯基膦)钯 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙二醇二甲醚 、 乙醚 、 环己烷 、 水 为溶剂， 反应 30.17h， 生成 1-benzyl-3-(2,2-dimethylpropyl)-5-methyl-1H-indole
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e

文献信息

• Indole Synthesis by Controlled Carbolithiation of <i>o</i>-Aminostyrenes
  作者：Albane Kessler、Claire M. Coleman、Patchanee Charoenying、Donal F. O'Shea

  DOI：10.1021/jo048723e

  日期：2004.11.1

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.