(1,4-二溴-3-苯基丁-2-烯-2-基)苯 | 7781-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (1,4-二溴-3-苯基丁-2-烯-2-基)苯
• 英文名称: 1,4-dibromo-2,3-diphenyl-2-butene
• 英文别名: 1,4-dibromo-2,3-diphenyl-but-2-ene；1,4-Dibrom-2,3-diphenyl-but-2-en；(1,4-dibromo-3-phenylbut-2-en-2-yl)benzene
• CAS: 7781-70-6
• 化学式: C₁₆H₁₄Br₂
• 分子量: 366.095
• InChiKey: LHQCGRPIRYILLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  373.4±37.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (1,4-二溴-3-苯基丁-2-烯-2-基)苯 生成 2-溴苯乙酮
  参考文献：
  名称：

  Salkind; Mossunow, Zhurnal Obshchei Khimii, 1940, vol. 10, p. 517,519

  摘要：

  DOI：
• 作为产物：
  描述：

  (1-氯乙烯基)苯 生成 (1,4-二溴-3-苯基丁-2-烯-2-基)苯
  参考文献：
  名称：

  Butadiene from vinyl chloride. Platinum(II)-catalyzed coupling of vinyl halides

  摘要：

  DOI：

  10.1021/jo01280a106

文献信息

• Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans
  作者：Chen Zhong、Qi Yin、Yukun Zhao、Qinfeng Li、Lin Hu

  DOI：10.1039/d0cc05565d

  日期：——

  A general [5+1] annulation reaction, which utilized 4-bromo- or 4-mesyloxy-but-2-enyl peroxides as unique five-atom bielectrophilic synthons to participate in the C–C and the subsequent umpolung C–O bond-forming reactions with C1 nucleophiles, has been developed for the facile synthesis of 2,2-disubstituted dihydropyrans in high yields under mild basic conditions. The dihydropyrans, which are readily

  一般的[5 + 1]环化反应，利用4-溴-或4-甲氧基-丁-2-烯基过氧化物作为独特的五原子双亲电合成子，参与C-C和随后的umpolung C-O键-已经开发了与C1亲核试剂的形成反应，用于在温和的碱性条件下以高收率容易地合成2，2-二取代的二氢吡喃。通过这种新方法很容易以克为单位制备的二氢吡喃，可以1-2步灵活地转化为生物学上重要的四氢吡喃和吡喃酮。
• Some Observations on the Reactions of α,α′-Dimethylstilbene and Related Compounds
  作者：Osamu Simamura、Hiroshi Suzuki

  DOI：10.1246/bcsj.27.231

  日期：1954.4

  Cis- and trans-α,α′-Dimethylstilbene, heated with a little sulfuric acid at 210°, were isomerized to an equilibrium mixture consisting of 55% of the trans and 45% of the cis isomers. Heated with iodine at 210°, they yielded meso-2,3-diphenylbutane. The action of bromine produced 1,4-dibromo-2,3-diphenyl-2-butene; under certain experimental conditions the concurrent cis-trans isomerization was observed

  顺式和反式-α,α'-二甲基二苯乙烯与少量硫酸一起在210°加热，异构化成由55%的反式和45%的顺式异构体组成的平衡混合物。在 210° 下用碘加热，产生内消旋-2,3-二苯基丁烷。溴作用生成1,4-二溴-2,3-二苯基-2-丁烯；在某些实验条件下，观察到同时发生的顺反异构化。这一事实，连同作为副产物的少量α-溴苯乙酮的分离，支持了反应通过涉及溴原子的机制进行的观点。检查了溴对一些 α,α'-二取代二苯乙烯的作用。观察到的反应是根据烯键上的大基团所产生的空间效应来讨论的。
• Facile, high yield synthesis of 2,3-diphenyl-1,3-butadiene
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04665257A1

  公开（公告）日：1987-05-12

  A high yield, four step synthesis process is disclosed for producing the omer, 2,3-diphenyl-1,3-butadiene, wherein in step 1 acetophenone pinacol is produced from the dimerization of acetophenone in 96% yield; in step 2 acetophenone pinacol is reacted with triethoxymethane and benzoic acid to produce 2,3-diphenyl-2-butene in about 88-96% yield. The 2,3-diphenyl-2-butene and N-bromosuccinimide (NBS) are reacted together in step 3 in an ultra violet reactor and in a CCl.sub.4 reaction solvent to produce in about 92% yield, the dibromo compound, 1,4-dibromo-2,3-diphenyl-2-butene. In step 4, 1,4-dibromo-2,3-diphenyl-2-butene is converted to the desired monomer in about 86% yield by reacting with NaI under refluxing conditions for about 90 minutes in a hot acetone solution. The monomer 2,3-diphenyl-1,3-butadiene is recovered in hexane, shaken (in the order listed) with water solutions of NaHSO.sub.3, NaHCO.sub.3, and pure water, dried over CaCl.sub.2, and the hexane is spun off. The residue is then recrystallized from hot methyl alcohol by the addition of water. The crystals which are air dried should be refrigerated as soon as possible to prevent spontaneous polymerization.

  本发明揭示了一种高产量的四步合成过程，用于生产2,3-二苯基-1,3-丁二烯，其中在第一步中，通过苯乙酮的二聚反应，以96％的收率产生苯乙酮皮纳科尔；在第二步中，苯乙酮皮纳科尔与三乙氧甲烷和苯甲酸反应，以约88-96％的收率产生2,3-二苯基-2-丁烯。在第三步中，2,3-二苯基-2-丁烯和N-溴代琥珀酰亚胺（NBS）在紫外反应器和CCl.sub.4反应溶剂中反应，以约92％的收率产生二溴化合物1,4-二溴-2,3-二苯基-2-丁烯。在第四步中，通过在热丙酮溶液中回流约90分钟，与NaI反应，以约86％的收率将1,4-二溴-2,3-二苯基-2-丁烯转化为所需的单体。单体2,3-二苯基-1,3-丁二烯在己烷中回收，按照顺序与NaHSO.sub.3、NaHCO.sub.3和纯水的水溶液混合，经CaCl.sub.2干燥，然后离心去除己烷。残渣随后通过加水在热甲醇中重结晶。晶体应尽快冷藏以防止自发聚合。
• Tunable Reaction Mode of Bifunctional Peroxides with Ketones to Access α-Oxacyclic Ketones and Enals
  作者：Xiaolu Wen、Min Gao、Yiwei Chen、Yukun Zhao、Wenling Qin、Lin Hu

  DOI：10.1021/acs.orglett.2c03440

  日期：2022.11.18

  A new annulation reaction between allylic/benzylic peroxides and ketones has been developed to provide the α-oxacyclic ketones in moderate yields under the KOtBu basic conditions. Mechanistic studies reveal that these peroxides undergo the Kornblum-DeLaMare rearrangement to release the aldehyde intermediates and subsequently initiate the aldol/etherification tandem process to deliver the final products

  已经开发了一种新的烯丙基/苄基过氧化物和酮之间的环化反应，以在 KO t Bu 碱性条件下以中等产率提供 α-氧杂环酮。机理研究表明，这些过氧化物经过 Kornblum-DeLaMare 重排以释放醛中间体，随后启动醛醇/醚化串联过程以提供最终产品。因此，这些用作“掩蔽”烯醛的过氧化物也已被用于一步制备以前难以实现的α-烯醛系链酮。
• Allen; Eliot; Bell, Canadian Journal of Research, Section B: Chemical Sciences, 1939, vol. 17, p. 75,87
  作者：Allen、Eliot、Bell

  DOI：——

  日期：——