tert-butyl 4-{[(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate | 293744-27-1

• 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-{[(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate
• 英文别名: Tert-butyl 4-[(2-bromo-4-methylphenyl)carbamoyl]piperidine-1-carboxylate
• CAS: 293744-27-1
• 化学式: C₁₈H₂₅BrN₂O₃
• 分子量: 397.312
• InChiKey: UIOBTXIZKFTHOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-{[(2-bromo-4-methylphenyl)amino]carbonyl}piperidine-1-carboxylate 在 [Pd(dibenzylideneacetone)2] potassium fluoride on basic alumina 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 为溶剂， 反应 220.5h， 生成 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：

  1-Boc-4-哌啶甲酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.42h， 生成 tert-butyl 4-{[(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

• Novel Spiroindoline or Spiroisoquinoline Compounds, Methods of Use and Compositions Thereof
  申请人：Boatman Douglas P.

  公开号：US20070254903A1

  公开（公告）日：2007-11-01

  The invention provides compounds of Formula (I): and pharmaceutically acceptable salts, solvates and stereoisomers thereof, wherein A, B, E, G, W, X, Y, Z, o, and R 1 are as disclosed herein (“Compound(s) of the Invention”), which are useful as cardio-protective and/or neuro-protective agents. The invention also provides pharmaceutical compositions comprising a Compound of the Invention and methods for treating, preventing and/or managing a vascular, cardiovascular or neurological disease or disorder, comprising administering to a patient in need thereof a Compound of the Invention.

  本发明提供了公式（I）的化合物及其药学上可接受的盐、溶剂合物和立体异构体，其中A、B、E、G、W、X、Y、Z、o和R1如本文所述（“本发明的化合物”），它们可用作心血管保护和/或神经保护剂。本发明还提供了包括本发明的化合物的制药组合物以及治疗、预防和/或管理血管、心血管或神经系统疾病或紊乱的方法，包括向需要该化合物的患者施用本发明的化合物。
• NOVEL SPIROINDOLINE OR SPIROISOQUINOLINE COMPOUNDS, METHODS OF USE AND COMPOSITIONS THEREOF
  申请人：Arena Pharmaceuticals, Inc.

  公开号：EP1716148A2

  公开（公告）日：2006-11-02
• [EN] NOVEL SPIROINDOLINE OR SPIROISOQUINOLINE COMPOUNDS, METHODS OF USE AND COMPOSITIONS THEREOF<br/>[FR] NOUVEAUX COMPOSES DE SPIROINDOLINE OU DE SPIROISOQUINOLINE, METHODES D'UTILISATION ET COMPOSITIONS ASSOCIEES
  申请人：ARENA PHARM INC

  公开号：WO2005063745A9

  公开（公告）日：2007-02-01

  [EN] The invention provides compounds of Formula (I): and pharmaceutically acceptable salts, solvates and stereoisomers thereof, wherein A, B, E, G, W, X, Y, Z, o, and R₁ are as disclosed herein ("Compound(s) of the Invention"), which are useful as cardio-protective and/or neuro-protective agents. The invention also provides pharmaceutical compositions comprising a Compound of the Invention and methods for treating, preventing and/or managing a vascular, cardiovascular or neurological disease or disorder, comprising administering to a patient in need thereof a Compound of the Invention.
  [FR] L'invention concerne des composés de formule (I) et des sels acceptables pharmaceutiquement, des solvates et des stéréo-isomères associés. Dans la formule (I), A, B, E, G, W, X, Y, Z, o, et R₁ sont tels que spécifiés dans l'invention (= composés de l'invention), et sont utilisés en tant qu'agents cardioprotecteurs et/ou neuroprotecteurs. Cette invention a aussi trait à des compositions pharmaceutiques renfermant un composé de l'invention et à des méthodes de traitement, de prévention et/ou de gestion d'une maladie ou d'un trouble vasculaire, cardio-vasculaire ou neurologique, lesdites méthodes consistant à administrer à un patient le nécessitant un composé de l'invention.
• ——
  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.