(6R)-4-benzyl-6-hydroxymethylpiperazin-2-one | 323592-87-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R)-4-benzyl-6-hydroxymethylpiperazin-2-one
• 英文别名: (6R)-4-benzyl-6-(hydroxymethyl)piperazin-2-one
• CAS: 323592-87-6
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: PPDBHJIKWGZCBH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6R)-4-benzyl-6-hydroxymethylpiperazin-2-one 在 palladium dihydroxide 、 palladium on activated charcoal potassium phosphate 、 copper(l) iodide 、 氢气 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 44.0h， 生成 (3R)-3-hydroxymethyl-4-(4-hydroxyphenyl)-5-oxopiperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Practical Synthesis of 1-Aryl-6-(hydroxymethyl)-2-ketopiperazines via a 6-exo Amide−Epoxide Cyclization

  摘要：

  Chiral 1-aryl-6-(hydroxymethyl)-2-ketopiperazines can be prepared via an operationally simple, 6-exo epoxide ring-opening cyclization to form the ketopiperazine C6-N1 bond in high yields and with excellent enantiomeric purity.

  DOI：

  10.1021/ol048235t
• 作为产物：
  描述：

  (S)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylic acid tert-butyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以69%的产率得到(6R)-4-benzyl-6-hydroxymethylpiperazin-2-one
  参考文献：
  名称：

  Practical Synthesis of 1-Aryl-6-(hydroxymethyl)-2-ketopiperazines via a 6-exo Amide−Epoxide Cyclization

  摘要：

  Chiral 1-aryl-6-(hydroxymethyl)-2-ketopiperazines can be prepared via an operationally simple, 6-exo epoxide ring-opening cyclization to form the ketopiperazine C6-N1 bond in high yields and with excellent enantiomeric purity.

  DOI：

  10.1021/ol048235t

文献信息

• [EN] PIPERAZINE DERIVATIVE RENIN INHIBITORS<br/>[FR] DERIVES DE PIPERAZINE AGISSANT COMME INHIBITEURS DE LA RENINE
  申请人：WARNER LAMBERT CO

  公开号：WO2004089915A1

  公开（公告）日：2004-10-21

  Disclosed are piperazine derivatives, their manufacture and use as inhibitors of renin. Formula (I):

  揭示了哌嗪衍生物，它们的制备以及作为肾素抑制剂的用途。化学式（I）：
• Piperazine derivative renin inhibitors
  申请人：——

  公开号：US20040214832A1

  公开（公告）日：2004-10-28

  Disclosed are piperazine derivatives, their manufacture and use as inhibitors of renin.

  本发明涉及哌嗪衍生物，它们的制备和用途作为肾素抑制剂。
• SUBSTITUTED OXOAZAHETEROCYCLYL COMPOUNDS
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1208097A2

  公开（公告）日：2002-05-29
• [EN] SUBSTITUTED OXOAZAHETEROCYCLYL COMPOUNDS<br/>[FR] COMPOSES D'OXOAZAHETEROCYCLYLE SUBSTITUE
  申请人：AVENTIS PHARM PROD INC

  公开号：WO2001007436A2

  公开（公告）日：2001-02-01

  This invention is directed to oxoazaheterocyclyl compounds which inhibit Factor Xa, to oxoazaheterocyclyl compounds which inhibit both Factor Xa and Factor IIa, to pharmaceutical compositions comprising these compounds, to intermediates useful for preparing these compounds, to a method of directly inhibiting Factor Xa and to a method of simultaneously directly inhibiting Factor Xa and Factor IIa.
• Practical Synthesis of 1-Aryl-6-(hydroxymethyl)-2-ketopiperazines via a 6-<i>exo</i> Amide−Epoxide Cyclization
  作者：Noel A. Powell、Fred L. Ciske、Emma C. Clay、Wayne L. Cody、Dennis M. Downing、Peter G. Blazecka、Daniel D. Holsworth、Jeremy J. Edmunds

  DOI：10.1021/ol048235t

  日期：2004.10.1

  Chiral 1-aryl-6-(hydroxymethyl)-2-ketopiperazines can be prepared via an operationally simple, 6-exo epoxide ring-opening cyclization to form the ketopiperazine C6-N1 bond in high yields and with excellent enantiomeric purity.