(Z)-2-Acetylamino-3-(4-bromo-phenyl)-acrylic acid methyl ester | 600730-82-3

• 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)-2-Acetylamino-3-(4-bromo-phenyl)-acrylic acid methyl ester
• 英文别名: Methyl 2-acetamido-3-(4-bromophenyl)prop-2-enoate
• CAS: 600730-82-3
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: UDPFLIRRGHZTJO-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±45.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-Acetylamino-3-(4-bromo-phenyl)-acrylic acid methyl ester 在 1,1'-bis(diisopropylphosphino)ferrocene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 2-乙酰氨基-3-(4-溴苯基)丙酸甲酯
  参考文献：
  名称：

  Chiral Rh phosphine–phosphite catalysts immobilized on ionic resins for the enantioselective hydrogenation of olefins in water

  摘要：

  Rh膦-膦酯手性催化剂固定在离子交换树脂上，在水中提供高度对映选择性的烯酰胺加氢。

  DOI：

  10.1039/c5gc00485c

文献信息

• Supramolecular chiral dendritic monophosphites assembled by hydrogen bonding and their use in the Rh-catalyzed asymmetric hydrogenation
  作者：Yong Li、Yan-Mei He、Zhi-Wei Li、Feng Zhang、Qing-Hua Fan

  DOI：10.1039/b823047a

  日期：——

  A new type of supramolecular chiral dendritic monophosphite ligands has been prepared via a hydrogen-bonding assembly. The Rh complexes of these supramolecular ligands have been successfully applied in the asymmetric hydrogenation of enamides and dehydroamino acid derivatives with good enantioselectivities, which are comparable to those obtained from the free monophosphite ligands. The supramolecular catalyst could be easily recycled viasolvent precipitation.

  通过氢键组装，制备了一类新型超分子手性树枝状单膦配体。这些超分子配体的铑配合物已成功应用于烯酰胺和脱氢氨基酸衍生物的不对称氢化反应，具有良好的对映选择性，与自由单膦配体获得的结果相当。超分子催化剂可通过溶剂沉淀轻松回收。
• Modular chiral dendritic monodentate phosphoramidite ligands for Rh(ii)-catalyzed asymmetric hydrogenation: unprecedented enhancement of enantioselectivity
  作者：Feng Zhang、Yong Li、Zhi-Wei Li、Yan-Mei He、Shou-Fei Zhu、Qing-Hua Fan、Qi-Lin Zhou

  DOI：10.1039/b815380a

  日期：——

  Modular chiral dendrimers with monodentate phosphoramidite ligands located at the core were synthesized and applied in the Rh-catalyzed asymmetric hydrogenations, afforded unprecedented enhancement of enantioselectivity.

  合成了位于核心的具有单齿亚磷酰胺配体的模块化手性树状大分子，并将其应用于Rh催化的不对称氢化中，提供了前所未有的对映选择性增强。
• Design and synthesis of a novel three-hindered quadrant bisphosphine ligand and its application in asymmetric hydrogenation
  作者：Kexuan Huang、Xiaowei Zhang、Thomas J. Emge、Guohua Hou、Bonan Cao、Xumu Zhang

  DOI：10.1039/c0cc02620d

  日期：——

  A novel three hindered quadrant bisphosphine ligand has been synthesized. The ligand shows excellent enantioselectivities and reactivities for rhodium-catalyzed hydrogenations of various functionalized olefins.

  合成了一种新型三阻碍四分之一双膦配体。该配体在铑催化的各种功能化烯烃氢化反应中表现出优异的对映选择性和反应活性。
• Enantioselective Hydrogenation of α-Dehydroamino Acid Esters Catalyzed by Rhodium Complexes with Chiral Bisaminophosphine Ligands
  作者：Xianfeng Sun、Wei Li、Le Zhou、Xumu Zhang

  DOI：10.1002/adsc.201000038

  日期：——

  A highly efficient strategy for the synthesis of a series of chiral bisaminophosphine ligands was well established with several remarkable features. The synthetic utility of these ligands was explored for rhodium‐catalyzed asymmetric hydrogenations of α‐dehydroamino acid esters. Up to 98% ee values were achieved for the enantioselective synthesis of aminocarboxylic acids and their derivatives, which

  具有一系列显着特征的合成手性双氨基膦配体的高效策略已得到很好的确立。探索了这些配体的合成用途，用于铑催化的α-脱氢氨基酸酯的不对称氢化。对氨基羧酸及其衍生物的对映选择性合成可达到高达98％的ee值，这是合成多种天然产物和生物活性分子非常重要的手性结构单元。
• A supramolecularly tunable chiral diphosphine ligand: application to Rh and Ir-catalyzed enantioselective hydrogenation
  作者：Xi-Chang Zhang、Yi-Hu Hu、Chuan-Fu Chen、Qiang Fang、Li-Yao Yang、Ying-Bo Lu、Lin-Jie Xie、Jing Wu、Shijun Li、Wenjun Fang

  DOI：10.1039/c6sc00589f

  日期：——

  A supramolecularly tunable chiral bisphosphine ligand bearing two pyridyl-containing crown ethers was synthesized and applied in Rh or Ir-catalyzed asymmetric hydrogenations in high yields with excellent ee values (90-99% ee).

  合成了带有两个含吡啶基的冠醚的超分子可调性手性双膦配体，并以优异的ee值（90-99％ee）以高收率应用于Rh或Ir催化的不对称氢化中。