methyl 2-bromo-3-(4-nitrophenyl)acrylate | 51738-11-5

• 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
• 英文名称: methyl 2-bromo-3-(4-nitrophenyl)acrylate
• 英文别名: 2-Brom-3-p-nitrophenyl-2-propensaeuremethylester；methyl 2-bromo-3-(4-nitrophenyl)prop-2-enoate
• CAS: 51738-11-5
• 化学式: C₁₀H₈BrNO₄
• 分子量: 286.082
• InChiKey: LMKMEBWSDLEAGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±27.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 甲氧羰基亚甲基三苯基正膦 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到methyl 2-bromo-3-(4-nitrophenyl)acrylate
  参考文献：
  名称：

  A Novel and Convenient Protocol for Synthesis of α-Haloacrylates

  摘要：

  A.novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide-ylide species might be involved as an intermediate.

  DOI：

  10.1021/ol702859y

文献信息

• Bis(2,2,2-trifluoroethyl)bromophosphonoacetate, a Novel HWE Reagent for the Preparation of (<i>E</i>)-α-Bromoacrylates:  A General and Stereoselective Method for the Synthesis of Trisubstituted Alkenes
  作者：Keiko Tago、Hiroshi Kogen

  DOI：10.1021/ol006074x

  日期：2000.6.1

  A novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (3a), was designed and prepared in order to efficiently synthesize (E)-alpha-bromoacrylates, which are useful precursors for various C-C bond formations. Honer-Wadsworth-Emmons (HWE) reaction of various aldehydes with 3a in the presence of t-BuOK and 18-C-6 gave the corresponding (E)-alpha-bromoacrylate derivatives with high stereoselectivity

  设计并制备了一种新颖的试剂，双（2,2,2-三氟乙氧基）溴代膦酰基乙酸甲酯（3a），以便有效地合成（E）-α-溴代丙烯酸酯，它们是形成各种CC键的有用前体。在t-BuOK和18-C-6存在下，各种醛与3a的Honer-Wadsworth-Emmons（HWE）反应产生具有高立体选择性的相应（E）-α-溴丙烯酸酯衍生物。使用（E）-α-溴丙烯酸酯作为关键中间体，开发了通过Pd催化的交叉偶联合成三取代烯烃的一般立体选择性合成方法。
• Stereoselective Synthesis of (2Z)-α-Bromo-α,β-Unsaturated esters via arsonium ylide
  作者：Zhi-Zhen Huang、Lu-Ling Wu、Liu-Shen Zhu、Xian Huang

  DOI：10.1080/00397919608086740

  日期：1996.2

  Abstract (2Z)-α-Bromo-α,β-unsaturated esters 6 can be synthesized stereoselective via arsonium ylides in good yields.

  摘要 (2Z)-α-溴-α,β-不饱和酯 6 可以立体选择性地通过砷叶立德合成，收率良好。
• A Novel and Convenient Protocol for Synthesis of α-Haloacrylates
  作者：Biao Jiang、Ying Dou、Xiangya Xu、Min Xu

  DOI：10.1021/ol702859y

  日期：2008.2.1

  A.novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide-ylide species might be involved as an intermediate.