(Z)-ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate | 888704-22-1

• 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: (Z)-ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate
• 英文别名: ethyl N-[(Z)-3-(butylamino)-2-cyanoprop-2-enoyl]carbamate
• CAS: 888704-22-1
• 化学式: C₁₁H₁₇N₃O₃
• 分子量: 239.274
• InChiKey: QVTVISMEVJEQTO-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 生成 1-butyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile
  参考文献：
  名称：

  NEt 3催化氨基甲酸酯分子内氨解的动力学和机理研究

  摘要：

  建议在乙腈或乙腈水溶液中NEt 3催化Z - 1的分子内氨解的机理包括通过同时进行H吸收和E2的乙醇排出来确定T ±的速率。证据包括乙腈中k H / k D = 1.66的主要同位素效应，缓冲水溶液中的普通碱催化作用，盐效应以及拟议中的水稳定速率决定性过渡态（TS1和TS2）。水滴定实验。

  DOI：

  10.1021/jo800306r
• 作为产物：
  描述：

  N-氰基乙酰尿烷 以 氘代氯仿 、 乙腈 为溶剂， 反应 4.08h， 生成 (Z)-ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate
  参考文献：
  名称：

  A multi-component reaction to 5-cyanouracils: Synthesis and mechanistic study

  摘要：

  Acetonitrile as a solvent, excess of primary amines as general bases, and a reflux condition make the multi-component reactions of (2-cyanoacetyl) carbamate 1, ethyl orthoformate, and primary amines form 5-cyanouracils 4a-c feasibly. Mechanistic studies of the multi-component reaction were carried out by proton NMR spectrometer. Acetonitrile as a solvent makes the reaction of 1 with ethyl orthoformate produce E-ethyl (2-cyano-3-ethoxyacryloyl) carbamate E-2 without a catalyst of acetic anhydride. The reactions of E-2 with primary amines produce the corresponding Z-3a-c as the only stable isomers eventually in CDCl3 or CD3CN. General-base-catalyzed intramolecular cyclizations of Z-3a-c at a reflux condition in CD3CN generated the corresponding 5-cyanouracils 4a-c. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.059

文献信息

• A multi-component reaction to 5-cyanouracils: Synthesis and mechanistic study
  作者：Bo-Ren Zhuang、Gien-Jow Hsu、Kuangsen Sung

  DOI：10.1016/j.bmc.2005.12.059

  日期：2006.5

  Acetonitrile as a solvent, excess of primary amines as general bases, and a reflux condition make the multi-component reactions of (2-cyanoacetyl) carbamate 1, ethyl orthoformate, and primary amines form 5-cyanouracils 4a-c feasibly. Mechanistic studies of the multi-component reaction were carried out by proton NMR spectrometer. Acetonitrile as a solvent makes the reaction of 1 with ethyl orthoformate produce E-ethyl (2-cyano-3-ethoxyacryloyl) carbamate E-2 without a catalyst of acetic anhydride. The reactions of E-2 with primary amines produce the corresponding Z-3a-c as the only stable isomers eventually in CDCl3 or CD3CN. General-base-catalyzed intramolecular cyclizations of Z-3a-c at a reflux condition in CD3CN generated the corresponding 5-cyanouracils 4a-c. (c) 2006 Elsevier Ltd. All rights reserved.
• Kinetic and Mechanistic Studies of NEt₃-Catalyzed Intramolecular Aminolysis of Carbamate
  作者：Kuangsen Sung、Bo-Ren Zhuang、Pin-Mei Huang、Sheng-Wei Jhong

  DOI：10.1021/jo800306r

  日期：2008.6.1

  The mechanism of the NEt3-catalyzed intramolecular aminolysis of Z-1 in acetonitrile or aqueous acetonitrile solutions is suggested to involve rate-determining collapse of T ± through simultaneous H-abstraction and ethoxide expulsion of E2 process. The evidence for that includes the primary isotope effect of kH/kD = 1.66 in acetonitrile, general-base catalysis in aqueous buffer solutions, salt effect

  建议在乙腈或乙腈水溶液中NEt 3催化Z - 1的分子内氨解的机理包括通过同时进行H吸收和E2的乙醇排出来确定T ±的速率。证据包括乙腈中k H / k D = 1.66的主要同位素效应，缓冲水溶液中的普通碱催化作用，盐效应以及拟议中的水稳定速率决定性过渡态（TS1和TS2）。水滴定实验。