tert-butyl 4-{[(benzyl)(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate | 293744-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 4-{[(benzyl)(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-[benzyl-(2-bromo-4-methylphenyl)carbamoyl]piperidine-1-carboxylate
• CAS: 293744-32-8
• 化学式: C₂₅H₃₁BrN₂O₃
• 分子量: 487.437
• InChiKey: HVMVQSUZESUJFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-{[(benzyl)(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate 在 [Pd(dibenzylideneacetone)2] R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.5h， 以78.3%的产率得到tert-butyl 1-benzyl-1,2-dihydro-5-methyl-2-oxospiro[3H-indole-3,4'-piperidine]-1'-carboxylate
  参考文献：
  名称：

  摘要：

  Starling from 1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid and 2-bromoaniline, the spiro[indole-3,4'-piperidin]-2-one system was obtained in three high-yielding steps: anilide formation, N(1)-protection, and intramolecular cyclization under Pd catalysis as the key reaction. The preparation of the corresponding 2-bromoanilide was studied. In extension, the same sequence was developed with 4-methyl- and 4-nitro-2-bromoaniline. In the key step, the NO, group led to a rather diminished yield. The transformation of the protected spiro[indole3,4'-piperidin] -2-one to the corresponding unprotected dihydroindoles is discussed.

  DOI：

  10.1002/1522-2675(20000607)83:6<1247::aid-hlca1247>3.0.co;2-1
• 作为产物：
  描述：

  4-氯羰基-哌啶-1-羧酸叔丁酯 在 吡啶 、 4-二甲氨基吡啶 、 potassium fluoride on basic alumina 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 230.0h， 生成 tert-butyl 4-{[(benzyl)(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate
  参考文献：
  名称：

  摘要：

  Starling from 1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid and 2-bromoaniline, the spiro[indole-3,4'-piperidin]-2-one system was obtained in three high-yielding steps: anilide formation, N(1)-protection, and intramolecular cyclization under Pd catalysis as the key reaction. The preparation of the corresponding 2-bromoanilide was studied. In extension, the same sequence was developed with 4-methyl- and 4-nitro-2-bromoaniline. In the key step, the NO, group led to a rather diminished yield. The transformation of the protected spiro[indole3,4'-piperidin] -2-one to the corresponding unprotected dihydroindoles is discussed.

  DOI：

  10.1002/1522-2675(20000607)83:6<1247::aid-hlca1247>3.0.co;2-1

文献信息

• ——
  作者：Ralf Freund、Werner W. K. R. Mederski

  DOI：10.1002/1522-2675(20000607)83:6<1247::aid-hlca1247>3.0.co;2-1

  日期：2000.6.7

  Starling from 1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid and 2-bromoaniline, the spiro[indole-3,4'-piperidin]-2-one system was obtained in three high-yielding steps: anilide formation, N(1)-protection, and intramolecular cyclization under Pd catalysis as the key reaction. The preparation of the corresponding 2-bromoanilide was studied. In extension, the same sequence was developed with 4-methyl- and 4-nitro-2-bromoaniline. In the key step, the NO, group led to a rather diminished yield. The transformation of the protected spiro[indole3,4'-piperidin] -2-one to the corresponding unprotected dihydroindoles is discussed.