4-{2-[N'-(2-Bromo-acetyl)-hydrazino]-2-oxo-1-phenyl-ethylidene}-piperidine-1-carboxylic acid tert-butyl ester | 874947-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{2-[N'-(2-Bromo-acetyl)-hydrazino]-2-oxo-1-phenyl-ethylidene}-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[2-[2-(2-bromoacetyl)hydrazinyl]-2-oxo-1-phenylethylidene]piperidine-1-carboxylate；tert-butyl 4-[2-[2-(2-bromoacetyl)hydrazinyl]-2-oxo-1-phenylethylidene]piperidine-1-carboxylate
• CAS: 874947-19-0
• 化学式: C₂₀H₂₆BrN₃O₄
• 分子量: 452.348
• InChiKey: OBHADEJANALXMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{2-[N'-(2-Bromo-acetyl)-hydrazino]-2-oxo-1-phenyl-ethylidene}-piperidine-1-carboxylic acid tert-butyl ester 在 六氯乙烷 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以53%的产率得到4-[(5-Bromomethyl-[1,3,4]oxadiazol-2-yl)-phenyl-methylene]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  General synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles

  摘要：

  Tetrasubstituted alkenyl-1,3,4-oxadiazoles were synthesized in moderate to excellent yield, under mild conditions and in the presence of sensitive functional groups, via the cyclization of diacylhydrazides using PPh3 and hexachloroethane in the presence of Hunig's base. An efficient one-pot acylation/cyclization approach for the conversion of acylhydrazides to 1,3,4-oxadiazoles is also described. The complexity of our substrate as well as the wide range of functional groups incorporated substantially broadens the scope of this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.057
• 作为产物：
  描述：

  4-(1-phenylmethylene-1-carboxylic acid)-piperidine-1-carboxylic acid tert-butyl ester 在 sodium carbonate 、 1-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 4-{2-[N'-(2-Bromo-acetyl)-hydrazino]-2-oxo-1-phenyl-ethylidene}-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  General synthesis of tetrasubstituted alkenyl-1,3,4-oxadiazoles

  摘要：

  Tetrasubstituted alkenyl-1,3,4-oxadiazoles were synthesized in moderate to excellent yield, under mild conditions and in the presence of sensitive functional groups, via the cyclization of diacylhydrazides using PPh3 and hexachloroethane in the presence of Hunig's base. An efficient one-pot acylation/cyclization approach for the conversion of acylhydrazides to 1,3,4-oxadiazoles is also described. The complexity of our substrate as well as the wide range of functional groups incorporated substantially broadens the scope of this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.057