1,2-双(溴乙炔基)苯 | 256439-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-双(溴乙炔基)苯
• 英文名称: 1,2-bis(bromoethynyl)benzene
• 英文别名: 1,2-Bis(2-bromoethynyl)benzene
• CAS: 256439-90-4
• 化学式: C₁₀H₄Br₂
• 分子量: 283.95
• InChiKey: QGCYQEHLSHXPKG-UHFFFAOYSA-N

物化性质

• 沸点：
  332.4±52.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2-双(溴乙炔基)苯 以 邻二氯苯 为溶剂， 以85%的产率得到2,3-二溴萘
  参考文献：
  名称：

  伯格曼反应作为一种综合工具：优点和局限性

  摘要：

  Bergman环芳烃化反应可有效地将易于制备的无环烯二炔转化为芳环。为了使用该反应制备更大的官能化稠合芳族体系，必须全面了解官能化如何影响环芳构化。在这里，我们介绍了三个不同功能化位点上取代基对环芳构化的影响以及如何对这些官能团进行定制以制备更复杂的系统的研究。

  DOI：

  10.1016/s0040-4020(01)00247-2
• 作为产物：
  描述：

  1,2-二碘苯 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 silver fluoride 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 23.0h， 生成 1,2-双(溴乙炔基)苯
  参考文献：
  名称：

  Fusing Triazoles: Toward Extending Aromaticity

  摘要：

  A novel method to extend aromaticity by one benzene and two triazole rings was developed and optimized. This two-step route employs the copper-catalyzed azide-haloalkyne cycloaddition reaction of an ortho-bis(iodoacetylene) system and the subsequent intramolecular homocoupling fusion of the neighboring iodotriazoles, a process in which an additional benzene ring is formed. This versatile methodology allows one to extend the core size of chromophores and, consequently, to tune the material's properties.

  DOI：

  10.1021/ol201290q

文献信息

• A Reiterative Approach to 2,3-Disubstituted Naphthalenes and Anthracenes
  作者：Daniel M. Bowles、John E. Anthony

  DOI：10.1021/ol991254w

  日期：2000.1.1

  trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene

  [反应：见正文]简单的双（溴乙炔基）亚芳基二炔很容易通过相应三甲基甲硅烷基衍生物的脱甲硅烷基卤化反应制得。这些卤代二炔的芳环芳香化导致否则难以以高收率制备2，3-二溴芳烃。所得卤代芳族化合物的炔基化可再生可溶的二炔体系，该体系被一个芳香环所同源。该迭代方法可以通过未取代的二炔的环芳构化来终止，从而提供简单的并苯烃。
• DBU‐Mediated Synthesis of Aryl Acetylenes or 1‐Bromoethynylarenes from Aldehydes
  作者：Yadagiri Thummala、Galla V. Karunakar、Venkata Ramana Doddi

  DOI：10.1002/adsc.201801334

  日期：2019.2

  sequential manner for the synthesis of arylacetylenes and 1,3‐enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1‐bromoalkynes intermediate

  两种众所周知的合成有机反应Ramirez烯化反应和Corey-fuchs反应以单锅顺序方式进行整合，以直接从市售醛开始合成芳基乙炔和1,3-烯炔。双环am1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）与添加剂NaOH不仅专门从醛中直接提供末端炔烃，而且还提高了反应速率。DBU的动态性质也促进了1-溴代炔烃中间产物的分离。从NaOH和H 2 O中选择添加剂可分别用作合成末端炔烃和1-溴代炔烃的开关。
• 3<i>H</i>-Benzophosphepine Complexes:  Versatile Phosphinidene Precursors
  作者：Mark L. G. Borst、Rosa E. Bulo、Danièle J. Gibney、Yonathan Alem、Frans J. J. de Kanter、Andreas W. Ehlers、Marius Schakel、Martin Lutz、Anthony L. Spek、Koop Lammertsma

  DOI：10.1021/ja054885w

  日期：2005.12.1

  The synthesis of a variety of benzophosphepine complexes [R = Ph, t-Bu, Me; MLn = W(CO)(5), Mo(CO)(5), Cr(CO)(5), Mn(CO)(2)Cp] by two successive hydrophosphinations of 1,2-diethynylbenzene is discussed in detail. The first hydrophosphination step proceeds at ambient temperature without additional promoters, and subsequent addition of base allows full conversion to benzophosphepines. Novel benzeno-1,4-diphosphinanes were isolated as side products. The benzophosphepine complexes themselves serve as convenient phosphinidene precursors at elevated, substituent-dependent temperatures (> 55 degrees C). Kinetic and computational analyses support the proposal that the phosphepine-phosphanorcaradiene isomerization is the rate-determining step. In the absence of substrate, addition of the transient phosphinidene to another benzophosphepine molecule is observed, and addition to 1,2-diethynylbenzene furnishes a delicate bidentate diphosphirene complex.
• The Bergman reaction as a synthetic tool: advantages and restrictions
  作者：Daniel M Bowles、Grant J Palmer、Chad A Landis、John L Scott、John E Anthony

  DOI：10.1016/s0040-4020(01)00247-2

  日期：2001.4

  The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on

  Bergman环芳烃化反应可有效地将易于制备的无环烯二炔转化为芳环。为了使用该反应制备更大的官能化稠合芳族体系，必须全面了解官能化如何影响环芳构化。在这里，我们介绍了三个不同功能化位点上取代基对环芳构化的影响以及如何对这些官能团进行定制以制备更复杂的系统的研究。
• Fusing Triazoles: Toward Extending Aromaticity
  作者：Michal Juríček、Kathleen Stout、Paul H. J. Kouwer、Alan E. Rowan

  DOI：10.1021/ol201290q

  日期：2011.7.1

  A novel method to extend aromaticity by one benzene and two triazole rings was developed and optimized. This two-step route employs the copper-catalyzed azide-haloalkyne cycloaddition reaction of an ortho-bis(iodoacetylene) system and the subsequent intramolecular homocoupling fusion of the neighboring iodotriazoles, a process in which an additional benzene ring is formed. This versatile methodology allows one to extend the core size of chromophores and, consequently, to tune the material's properties.