1-(3-溴甲基-2-甲基-吲哚-1-基)-乙酮 | 104918-07-2

• 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
• 中文名称: 1-(3-溴甲基-2-甲基-吲哚-1-基)-乙酮
• 英文名称: 1-(3-Bromomethyl-2-methyl-indol-1-yl)-ethanone
• 英文别名: 1-[3-(Bromomethyl)-2-methylindol-1-yl]ethanone
• CAS: 104918-07-2
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.137
• InChiKey: FZUBPQZAWRUUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-溴甲基-2-甲基-吲哚-1-基)-乙酮 在 柠檬酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (R)-ethyl 2-methyltryptophan
  参考文献：
  名称：

  A three-step, highly enantioselective synthesis of (R)-2-methyl tryptophane ethyl ester: Comparison with chemical resolution

  摘要：

  (R)-2-Methyltryptopban ethyl ester, (R)-2, having an enantiomeric purity >,=96% was obtained in 3 steps and using (SSS)-hydroxypinanone, 1, as the recoverable chiral auxiliary. The synthesis of the alkylating agent, 5a, was improved (to a reproduceble 55% overall yield from 2,3-dimethylindole). The resolution of racemic-2 through chromatographic separation of the corresponding iminoester derived from (RRR)-1 also proved to be easy and efficient (similar to 25% yield). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00633-9
• 作为产物：
  描述：

  1-(2,3-二甲基吲哚-1-基)乙酮 在 TEA 、 氢溴酸 、 溴 、 sodium bromide 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 1-(3-溴甲基-2-甲基-吲哚-1-基)-乙酮
  参考文献：
  名称：

  A three-step, highly enantioselective synthesis of (R)-2-methyl tryptophane ethyl ester: Comparison with chemical resolution

  摘要：

  (R)-2-Methyltryptopban ethyl ester, (R)-2, having an enantiomeric purity >,=96% was obtained in 3 steps and using (SSS)-hydroxypinanone, 1, as the recoverable chiral auxiliary. The synthesis of the alkylating agent, 5a, was improved (to a reproduceble 55% overall yield from 2,3-dimethylindole). The resolution of racemic-2 through chromatographic separation of the corresponding iminoester derived from (RRR)-1 also proved to be easy and efficient (similar to 25% yield). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00633-9

文献信息

• Selective side-chain bromination of n-acyl-2,3-dialkylindoles: synthesis and chemical modification of pyrrolo[1,2-a]indoles
  作者：Susan F. Vice、Catherine R. Copeland、Steven P. Forsey、Gary I. Dmitrienko

  DOI：10.1016/s0040-4039(00)95008-1

  日期：1985.1
• VICE, S. F.;COPELAND, C. R.;FORSEY, S. P.;DMITRIENKO, G. I., TETRAHEDRON LETT., 1985, 26, N 43, 5253-5256
  作者：VICE, S. F.、COPELAND, C. R.、FORSEY, S. P.、DMITRIENKO, G. I.

  DOI：——

  日期：——
• A three-step, highly enantioselective synthesis of (R)-2-methyl tryptophane ethyl ester: Comparison with chemical resolution
  作者：Arlette Solladié-Cavallo、Johanes Schwarz、Cyrille Mouza

  DOI：10.1016/s0040-4039(98)00633-9

  日期：1998.5

  (R)-2-Methyltryptopban ethyl ester, (R)-2, having an enantiomeric purity >,=96% was obtained in 3 steps and using (SSS)-hydroxypinanone, 1, as the recoverable chiral auxiliary. The synthesis of the alkylating agent, 5a, was improved (to a reproduceble 55% overall yield from 2,3-dimethylindole). The resolution of racemic-2 through chromatographic separation of the corresponding iminoester derived from (RRR)-1 also proved to be easy and efficient (similar to 25% yield). (C) 1998 Elsevier Science Ltd. All rights reserved.