(Z)-3-氨基-3-(4-溴苯基)丙烯酸乙酯 | 65939-94-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (Z)-3-氨基-3-(4-溴苯基)丙烯酸乙酯
• 英文名称: ethyl (Z)-3-amino-3-(4-bromophenyl)acrylate
• 英文别名: ethyl (Z)-3-amino-3-(4-bromophenyl)prop-2-enoate
• CAS: 65939-94-8
• 化学式: C₁₁H₁₂BrNO₂
• 分子量: 270.126
• InChiKey: GGKNKAAFXHKJNR-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-氨基-3-(4-溴苯基)丙烯酸乙酯 在 吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 (E)-3-Amino-2-{(Z)-2-[(E)-2-amino-2-(4-bromo-phenyl)-1-ethoxycarbonyl-vinylsulfanyl]-1,2-dicyano-vinylsulfanyl}-3-(4-bromo-phenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  4-氯-5 h -1,2,3-二噻唑-5-硫酮与α，β-不饱和β-氨基酯的反应：2- [2-（1-链烯基硫烷基-1-烷氧基羰基-2-氨基]的形成）-1,2-二氰基乙烯基硫烷基] -3-氨基-2-链烯基烷基酯

  摘要：

  在吡啶（2当量）在二氯甲烷中回流下，用3-烷基（或芳基）-3-氨基-2-丙烯酸烷基酯处理4-氯-5 H -1,2,3-二噻唑-5-硫酮得到2- [2-（1- alkenylsulfanyl-1-烷氧基羰基-2-氨基）-1,2- dicyanovinylsulfanyl] - 4和-1,2- dicyanovinyldisulfanyl] -3-氨基-2-链烯酸烷基酯7在产率分别为16％至60％和8％至48％。

  DOI：

  10.1002/jhet.5570390103
• 作为产物：
  描述：

  (4-溴苯甲酰)乙酸乙酯 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (Z)-3-氨基-3-(4-溴苯基)丙烯酸乙酯
  参考文献：
  名称：

  烯胺和芳基重氮盐的电氧化偶联区域选择性合成 N2-芳基 1,2,3-三唑

  摘要：

  通过在无金属条件下的连续 C-N 键形成和电氧化 N-N 偶联，报道了一种构建N 2 -芳基 1,2,3-三唑的有效合成路线。容易获得的 2-氨基丙烯酸酯和芳基重氮盐被用作起始材料，所开发的协议显示出优异的官能团耐受性，允许广泛的底物范围，高达 91% 的分离产率。各种机理研究，以及中间加合物的分离，是指连续的离子和自由基反应序列。

  DOI：

  10.1021/acs.orglett.1c04099

文献信息

• Trifluoroethanol as a Unique Additive for the Chemoselective Electrooxidation of Enamines to Access Unsymmetrically Substituted NH‐Pyrroles
  作者：Mrinmay Baidya、Debabrata Maiti、Lisa Roy、Suman De Sarkar

  DOI：10.1002/anie.202111679

  日期：2022.1.26

  A chemoselective electrooxidative heterocoupling of two different enamines is reported for the synthesis of unsymmetrically substituted NH-pyrroles. A “magic effect” of the additive trifluoroethanol is utilized to achieve the desired chemoselectivity by tuning the oxidation potentials and controlling the activation energy of the rate-determining step.

  据报道，两种不同烯胺的化学选择性电氧化杂偶联可用于合成不对称取代的 NH-吡咯。添加剂三氟乙醇的“神奇效应”用于通过调节氧化电位和控制速率决定步骤的活化能来实现所需的化学选择性。
• Synthesis of highly substituted pyrroles via oxidative free radical reactions of β-aminocinnamates
  作者：An-I Tsai、Che-Ping Chuang

  DOI：10.1016/j.tet.2005.12.011

  日期：2006.3

  reactions of β-aminocinnamates are described. Imine radicals produced by tetra-n-butylammonium cerium(IV) nitrate (TBACN) oxidation of enamines undergo efficient addition to the C–C double bond of β-aminocinnamates. This TBACN mediated free radical reaction between β-aminocinnamates and enamines provides a novel method for the synthesis of highly substituted pyrroles. The direct TBACN oxidation of β-aminocinnamates

  描述了β-氨基肉桂酸酯的氧化自由基反应。硝酸四正丁基铵铈（IV）（TBACN）氧化烯胺所产生的亚胺基要经过有效的加成反应，形成β-氨基肉桂酸酯的C-C双键。这种TBACN介导的β-氨基肉桂酸酯和烯胺之间的自由基反应为合成高度取代的吡咯提供了一种新颖的方法。β-氨基肉桂酸酯的直接TBACN氧化有效地产生了二聚产物。
• Method for producing an optically activ beta-amino acid
  申请人：——

  公开号：US20040023344A1

  公开（公告）日：2004-02-05

  The Problem to Be Solved: To provide a producing method of an optically active &bgr;-amino acid useful as intermediate for the production of medicines, agricultural chemicals and physiologically active substances, by means of a catalytic and asymmetric synthesis method of high performance and a high enantiomeric excess, without requiring additional procedures such as introduction and removal of protecting group and so on. Means to Solve the Problems: A producing method of an optically active &bgr;-amino acids which comprises subjecting an enamine to an asymmetric hydrogenation.

  需要解决的问题：提供一种光学活性的β-氨基酸生产方法，作为制药、农药和生理活性物质的中间体，通过高性能和高对映体过量的催化不对称合成方法，而不需要额外的保护基引入和去除等程序。 解决问题的方法：一种生产光学活性β-氨基酸的方法，包括将恩酰胺进行不对称氢化。
• CuI-catalyzed synthesis of multisubstituted pyrido[1,2-<i>a</i>]pyrimidin-4-ones through tandem Ullmann-type C–N cross-coupling and intramolecular amidation reaction
  作者：Baichuan Mo、Chunxia Chen、Jinsong Peng

  DOI：10.1039/d3ra04454h

  日期：——

  2-a]pyrimidin-4-ones were synthesized via a one-pot tandem CuI-catalyzed C–N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol features simple operation, broad substrate scope, good functional group tolerance and gram scale preparation, thus allowing practical and modular synthesis of pyrido[1,2-a]pyrimidin-4-ones from readily available 2-halopyridine and (Z)-3-amino-3-arylacrylate

  通过一锅串联 CuI 催化 C-N 键形成/分子内酰胺化反应在 130 °C DMF 中合成各种多取代吡啶并[1,2- a ]嘧啶-4-酮。该方案具有操作简单、底物范围广、官能团耐受性好和克级制备的特点，从而可以从容易获得的2-卤代吡啶和( Z )-吡啶并[1,2- a ]嘧啶-4-酮进行实用和模块化合成。 3-氨基-3-芳基丙烯酸酯的产率良好至优异。
• Diversity-Oriented Synthesis of Privileged Benzopyranyl Heterocycles from <i>s</i>-<i>cis</i>-Enones
  作者：Heeseon An、Sung-Jin Eum、Minseob Koh、Sung Kwang Lee、Seung Bum Park

  DOI：10.1021/jo702196f

  日期：2008.3.1

  [Graphics]A novel strategy for the construction of benzopyranyl heterocyclic series with maximized diversity in the polar surface area on rigid scaffolds has been developed through a divergent synthetic pathway with high efficiency. s-cis-Enones embedded in a benzopyran skeleton were identified as versatile key intermediates for the synthesis of four different heterocycle libraries fused with a benzopyran substructure. These four novel core skeletons were designed by a creative recombination of the privileged skeletons: benzopyran, pyridine, pyrazole, pyrazolopyrimidine, and pyrimidine. The regioselective synthesis of each core skeleton was achieved by the introduction of three s-cis enone intermediates. This paper also explores the regioselective formation of arylpyrazole through the condensation of beta-keto aldehyde with arylhydrazine under three different conditions and presents the mechanistic information that was obtained from the regioisomeric ratio of arylpyrazole based on the substituent's electronic effect and reaction temperature. It appears that the regioselective synthesis of arylpyrazole was achieved through the intriguing interplay of the nucleophilicity on arylhydrazine and the electrophilicity on dielectrophiles.