1-(1-bromovinyl)-4-nitrobenzene | 64600-19-7

• 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: 1-(1-bromovinyl)-4-nitrobenzene
• 英文别名: p-Nitro-α-Bromstyrol；4-Nitro-α-brom-styrol；1-(1-Bromoethenyl)-4-nitrobenzene
• CAS: 64600-19-7
• 化学式: C₈H₆BrNO₂
• 分子量: 228.045
• InChiKey: ZFZQVVWJEJOWQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-bromovinyl)-4-nitrobenzene 、 2,3-bis(pinacolatoboryl)-1,3-butadiene 在 二(三叔丁基膦)钯 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以48%的产率得到
  参考文献：
  名称：

  基于 2,3-双(频哪醇)硼基-1,3-丁二烯的交叉偶联反应的树枝烯的简便合成

  摘要：

  钯催化的 2,3-二硼基 1,3-丁二烯与链烯基卤化物或二烯基卤化物的交叉偶联反应使我们能够直接制备各种无环交叉共轭多烯，即树枝状烯。本方法不仅适用于对称[4]-和[6]树枝烯的合成，也适用于不对称[3]-至[5]树枝烯的合成。

  DOI：

  10.1246/cl.2004.1066
• 作为产物：
  描述：

  1-乙炔基-4-硝基苯 在 二溴甲烷 作用下， 以 N,N-二甲基苯胺 为溶剂， 反应 12.0h， 以76%的产率得到1-(1-bromovinyl)-4-nitrobenzene
  参考文献：
  名称：

  Metal-free regioselective hydrobromination of alkynes through C H/C Br activation

  摘要：

  A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ 'HBr' source. This protocol also represents an elegant example of the activation of sp(2) C-H and C-Br bonds in one pot, in which 'HBr' is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.070

文献信息

• Synthesis of epoxides with electronegative substituents. Photometric substrates for epoxide hydrase
  作者：Robert P. Hanzlik、James M. Hilbert

  DOI：10.1021/jo00398a019

  日期：1978.2
• Metal-free regioselective hydrobromination of alkynes through C H/C Br activation
  作者：Xiuling Chen、Tieqiao Chen、Yuqiang Xiang、Yongbo Zhou、Daoqing Han、Li-Biao Han、Shuang-Feng Yin

  DOI：10.1016/j.tetlet.2014.06.070

  日期：2014.8

  A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ 'HBr' source. This protocol also represents an elegant example of the activation of sp(2) C-H and C-Br bonds in one pot, in which 'HBr' is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed. (C) 2014 Elsevier Ltd. All rights reserved.
• Facile Synthesis of Dendralenes Based on the Cross-coupling Reaction of 2,3-Bis(pinacolato)boryl-1,3-butadiene
  作者：Masaki Shimizu、Kei Tanaka、Takuya Kurahashi、Katsuhiro Shimono、Tamejiro Hiyama

  DOI：10.1246/cl.2004.1066

  日期：2004.8

  Palladium-catalyzed cross-coupling reaction of 2,3-diboryl1,3-butadiene with an alkenyl halide or a dienyl halide allowed us to straightforwardly prepare various kinds of acyclic cross-conjugated polyenes that are referred to as dendralenes. The present method is applicable to the synthesis of not only symmetrical [4]- and [6]dendralenes but also unsymmetrical [3]-to [5]dendralenes.

  钯催化的 2,3-二硼基 1,3-丁二烯与链烯基卤化物或二烯基卤化物的交叉偶联反应使我们能够直接制备各种无环交叉共轭多烯，即树枝状烯。本方法不仅适用于对称[4]-和[6]树枝烯的合成，也适用于不对称[3]-至[5]树枝烯的合成。