(Z)-2-bromovinyl benzoate | 154116-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-bromovinyl benzoate
• 英文别名: [(Z)-2-bromoethenyl] benzoate
• CAS: 154116-00-4
• 化学式: C₉H₇BrO₂
• 分子量: 227.057
• InChiKey: LYEFPHUEKMBKOX-SREVYHEPSA-N

物化性质

• 沸点：
  261.5±32.0 °C(predicted)
• 密度：
  1.507±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-bromovinyl benzoate 、 4-(benzyloxy)but-1-enylboronic acid 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以68%的产率得到Benzoic acid (1Z,3E)-6-benzyloxy-hexa-1,3-dienyl ester
  参考文献：
  名称：

  A Novel Method for the Construction of (Z,E)- or (Z,Z)-Conjugated Alkadienyl Carboxylates

  摘要：

  [GRAPHICS]The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degreesC. The first investigation on the Suzuki-type cross-coupling of (2)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.

  DOI：

  10.1021/ol026286p
• 作为产物：
  描述：

  1,2-dibromoethyl benzoate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 对苯二酚 作用下， 生成 (Z)-2-bromovinyl benzoate
  参考文献：
  名称：

  A Novel Method for the Construction of (Z,E)- or (Z,Z)-Conjugated Alkadienyl Carboxylates

  摘要：

  [GRAPHICS]The stereocontrolled dehydrobromination of 1,2-dibromoethyl carboxylates giving (Z)-2-bromovinyl carboxylates could readily be approached by using DBU and a catalytic amount of hydroquinone as a base at -78 degreesC. The first investigation on the Suzuki-type cross-coupling of (2)-2-bromovinyl carboxylates as electrophiles with stereodefined alkenylboronic acids provides a novel method for the construction of (Z,E)or (Z,Z)-conjugated alkadienyl carboxylate moieties, which are often present in a range of natural products.

  DOI：

  10.1021/ol026286p

文献信息

• Nucleophilic vinylic substitutions of (Z)-(2-aroyloxyvinyl)phenyl-λ3-iodanes with tetrabutylammonium halides: vinylic SN2 reactions and ligand coupling on iodine(III)
  作者：Masahito Ochiai、Yoshio Nishi、Masaya Hirobe

  DOI：10.1016/j.tetlet.2005.01.101

  日期：2005.3

  readily prepared from ethynyl(phenyl)(tetrafluoroborato)-λ3-iodane via stereoselective Michael-type addition of benzoic acids in methanol in the presence of sodium benzoates, with tetrabutylammonium halides in THF at 65 °C results in a vinylic SN2 reaction to give the inverted (E)-β-benzoyloxyvinyl halides in high yields.

  的治疗（ż） - （β-benzoyloxyvinyl）苯基λ 3个-iodanes，从乙炔基（苯基）容易地制备（tetrafluoroborato）-λ 3经由立体选择性迈克尔加成的苯甲酸在甲醇中的钠甲酸酯的存在-iodane与四丁基铵卤化物在THF中于65°C进行乙烯基S N 2反应，可以高产率得到反相的（E）-β-苯甲酰氧基乙烯基卤化物。
• Halo Enol Phosphates: Regioselective Synthesis of Phosphatase Inactivators via a Complex-Induced Proximity Effect
  作者：Jeffrey K. Stowell、Theodore S. Widlanski

  DOI：10.1021/ja00081a058

  日期：1994.1