N-(4-Methylphenyl)pivalohydroxamsaeure | 111750-21-1

• 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: N-(4-Methylphenyl)pivalohydroxamsaeure
• 英文别名: N-(4-methylphenyl)-N-hydroxy-2,2-dimethylpropanamide；N-Hydroxy-2,2-dimethyl-N-(4-methylphenyl)propanamide
• CAS: 111750-21-1
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: DDZIUXFTMBMNEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基乙烯基亚砜 、 N-(4-Methylphenyl)pivalohydroxamsaeure 在 sodium hydride 作用下， 生成 2-Benzenesulfinyl-1-p-tolyl-aziridine
  参考文献：
  名称：

  N-hydroxy-N-pivaloylanilines: a new aziridinating agent

  摘要：

  描述了由异羟肟酸和缺电子烯烃有效合成2-官能化N-芳基氮丙啶的方法。

  DOI：

  10.1039/c39930000038
• 作为产物：
  描述：

  N-(对甲苯基)羟胺 、 三甲基乙酰氯 在 碳酸氢钠 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以88%的产率得到N-(4-Methylphenyl)pivalohydroxamsaeure
  参考文献：
  名称：

  Meier, Chris; Boche, Gernot, Chemische Berichte, 1990, vol. 123, # 8, p. 1691 - 1698

  摘要：

  DOI：

文献信息

• A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis
  作者：João Aires-de-Sousa、Ana M Lobo、Sundaresan Prabhakar

  DOI：10.1016/0040-4039(96)00490-x

  日期：1996.4

  Chiral N-arylaziridines are obtained from N-acyl-N-arylhydroxylamines using quaternary salts of Cinchona alkaloids as phase-transfer catalysts.

  使用金鸡纳生物碱的季盐作为相转移催化剂，从N-酰基-N-芳基羟胺获得手性N-芳基氮丙啶。
• Meier, Chris; Boche, Gernot, Chemische Berichte, 1990, vol. 123, # 8, p. 1691 - 1698
  作者：Meier, Chris、Boche, Gernot

  DOI：——

  日期：——
• MEIER, CHRIS;BOCHE, GERNOT, CHEM. BER., 123,(1990) N, C. 1691-1698
  作者：MEIER, CHRIS、BOCHE, GERNOT

  DOI：——

  日期：——
• Asymmetric synthesis of N-aryl aziridines
  作者：João Aires-de-Sousa、Sundaresan Prabhakar、Ana M. Lobo、Ana M. Rosa、Mário J.S. Gomes、Marta C. Corvo、David J. Williams、Andrew J.P. White

  DOI：10.1016/s0957-4166(01)00548-1

  日期：2002.1

  The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantio selection and a mechanism is proposed for the aziridination reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.
• N-hydroxy-N-pivaloylanilines: a new aziridinating agent
  作者：M. Manuela Pereira、Pedro P. O. Santos、Lucinda V. Reis、Ana M. Lobo、Sundaresan Prabhakar

  DOI：10.1039/c39930000038

  日期：——

  An efficient synthesis of 2-functionalised N-arylaziridines from hydroxamic acids and electron deficient olefins is described.

  描述了由异羟肟酸和缺电子烯烃有效合成2-官能化N-芳基氮丙啶的方法。