(Z)-1,2-Dibromo-1-(4-methylphenyl)ethylene | 74346-16-0

• 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)-1,2-Dibromo-1-(4-methylphenyl)ethylene
• 英文别名: (Z)-1-(1,2-dibromovinyl)-4-methylbenzene；(Z)-1,2-dibromo-p-methylstyrene；cis-1,2-Dibrom-(4-methylphenyl)ethylen；1-[(Z)-1,2-dibromoethenyl]-4-methylbenzene
• CAS: 74346-16-0
• 化学式: C₉H₈Br₂
• 分子量: 275.971
• InChiKey: ZZXLIZVZGZRJJH-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 (Z)-1,2-Dibromo-1-(4-methylphenyl)ethylene 在 sodium fluoride 作用下， 反应 27.0h， 生成 (E)-2-(2-bromo-2-p-tolylvinyl)tetrahydrofuran 、 (Z)-2-(2-bromo-2-p-tolylvinyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides

  摘要：

  An efficient and general method for the synthesis of 2-alkynyltetrahydrofuran was developed. The regioselective functionalization of the C(sp(3))-H bond adjacent to an oxygen atom with various alkynyl bromides has been achieved under transition-metal-free reaction conditions. Sodium fluoride was found, for the first time, to promote the efficient functionalization process remarkably. Moreover, 1,2-dibromostyrenes were also found to be effective in this method forming 2-alkenyltetrahydrofurans.

  DOI：

  10.1055/s-0033-1338534
• 作为产物：
  描述：

  4-甲苯基乙炔 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (E)-1-(1,2-dibromovinyl)-4-methylbenzene 、 (Z)-1,2-Dibromo-1-(4-methylphenyl)ethylene
  参考文献：
  名称：

  Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides

  摘要：

  1,2-Dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides can be selectively realized through using different reaction conditions. alpha,beta-Dihalo alkenes were obtained exclusively using THF as solvent without using any catalyst, while alpha,alpha-dihalo ketones were synthesized using a mixed solvent of THF and H2O in the presence of FeCl3 center dot 6H(2)O. Terminal aromatic alkynes are smoothly transformed into alpha,alpha-dihalo ketones on water without a catalyst. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.047

文献信息

• Reaction of ketone hydrazones with TeCl₄: isolation and reactions of novel divinyl telluride
  作者：Kentaro Okuma、Yuxuan Qu、Aoi Suetome、Noriyoshi Nagahora

  DOI：10.1039/d0ob00782j

  日期：——

  The reaction of acetophenone hydrazones with TeCl4 in the presence of DBU gave a mixture of divinyl ditellurides and divinyl tellurides, which easily reacted with Cu powder in refluxing toluene to afford divinyl tellurides in good yields. The reaction of divinyl tellurides with bromine (1.2 eq.) gave the corresponding tellurium dibromide rather than the addition of the double bond whereas 3 molar amount

  在DBU存在下，苯乙酮hydr与TeCl 4反应，得到二乙烯基二碲化物和二乙烯基碲化物的混合物，它们很容易在回流的甲苯中与铜粉反应，从而以良好的收率得到二乙烯基碲化物。二乙烯基碲化物与溴（1.2当量）的反应生成了相应的二溴化碲，而不是添加了双键，而3摩尔的溴生成了过量的溴化和氧化产物。二乙烯基碲化物与2-（三甲基甲硅烷基）苯基三氟甲磺酸酯在CsF存在下的反应以良好的收率得到了（E）-2-烯基二芳基碲化物。
• Vinyl cation intermediates in solvolytic and electrophilic reactions. 2. Bromination of arylacetylenes
  作者：Keith Yates、George Mandrapilias

  DOI：10.1021/jo01307a033

  日期：1980.9