(E)-ethyl 3-(N-hydroxy-N-phenylcarbamoyl)acrylate | 1030842-61-5

• 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: (E)-ethyl 3-(N-hydroxy-N-phenylcarbamoyl)acrylate
• 英文别名: ethyl (E)-3-(N-hydroxy-N-phenyl-carbamoyl)-acrylate；ethyl (E)-4-(N-hydroxyanilino)-4-oxobut-2-enoate
• CAS: 1030842-61-5
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: WELCHPNYZBFRKC-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式-4-氧基-2-丁烯酸乙酯 、 亚硝基苯 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以99%的产率得到(E)-ethyl 3-(N-hydroxy-N-phenylcarbamoyl)acrylate
  参考文献：
  名称：

  N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds

  摘要：

  NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of a-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.

  DOI：

  10.1021/ol8004276

文献信息

• N-HETEROCYCLIC CARBENE (NHC) CATALYZED SYNTHESIS OF HYDROXAMIC ACIDS
  申请人：Zhang Yugen

  公开号：US20100105921A1

  公开（公告）日：2010-04-29

  A process for preparing hydroxamic acids is provided. The process comprises reacting an aldehyde with a nitroso compound in the presence of a N-heterocyclic carbene (NHC) catalyst.

  提供了一种制备羟肟酸的过程。该过程包括在N-杂环卡宾（NHC）催化剂的存在下将醛与亚硝基化合物反应。
• N-heterocyclic carbene (NHC) catalyzed synthesis of hydroxamic acids
  申请人：Agency for Science, Technology and Research

  公开号：US08143423B2

  公开（公告）日：2012-03-27

  A process for preparing hydroxamic acids is provided. The process comprises reacting an aldehyde with a nitroso compound in the presence of a N-heterocyclic carbene (NHC) catalyst.

  提供了一种制备羟肟酸的方法。该方法包括在N-杂环卡宾（NHC）催化剂的存在下，将醛与亚硝基化合物反应。
• WO2008/115153
  申请人：——

  公开号：——

  公开（公告）日：——
• US8143423B2
  申请人：——

  公开号：US8143423B2

  公开（公告）日：2012-03-27
• N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
  作者：Fong Tian Wong、Pranab K. Patra、Jayasree Seayad、Yugen Zhang、Jackie Y. Ying

  DOI：10.1021/ol8004276

  日期：2008.6.1

  NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of a-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.