(E)-2,3-dibromo-1,4-diphenylbut-2-ene-1,4-dione | 54723-12-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (E)-2,3-dibromo-1,4-diphenylbut-2-ene-1,4-dione
• CAS: 54723-12-5
• 化学式: C₁₆H₁₀Br₂O₂
• 分子量: 394.062
• InChiKey: WYBKSZUTKGRPNK-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,3-dibromo-1,4-diphenylbut-2-ene-1,4-dione 在 1-methyl-3-pentyl-1H-imidazolium tetrafluoroborate 作用下， 反应 0.03h， 以89%的产率得到二苯甲酰基乙炔
  参考文献：
  名称：

  Catalysis by Ionic Liquid. A Green Protocol for the Stereoselective Debromination of vicinal-Dibromides by [pmIm]BF₄ under Microwave Irradiation

  摘要：

  [GRAPHIC]An easily accessible ionic liquid, 1-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, has been demonstrated to be an efficient catalyst as well as reaction medium for the stereoselective debromination of a variety of structurally diverse vicinal-dibromides to the corresponding (E)-alkenes in high yields under microwave irradiation. This reaction does not require any organic solvent and any metal or any conventional reducing agent, and the ionic liquid is recycled without any appreciable loss of its catalytic efficiency.

  DOI：

  10.1021/jo051373r
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 作用下， 生成 (E)-2,3-dibromo-1,4-diphenylbut-2-ene-1,4-dione
  参考文献：
  名称：

  THE SYNTHESIS AND CONFIGURATIONS OF UNSATURATED 1,4-DIKETONES AND KETONIC ACIDS, AND THE STEREOCHEMICAL MECHANISM OF THE ADDITION OF BROMINE. STUDIES ON UNSATURATED 1,4-DIKETONES. VI

  摘要：

  DOI：

  10.1021/ja01371a065

文献信息

• Substituent Effect in the Synthesis of α,α‐Dibromoketones, 1,2‐Dibromalkenes, and 1,2‐Diketones from the Reaction of Alkynes and Dibromoisocyanuric Acid
  作者：Eunjeong Cho、Aravindan Jayaraman、Junseong Lee、Kyoung Chul Ko、Sunwoo Lee

  DOI：10.1002/adsc.201801535

  日期：2019.4.16

  dibromoisocyanuric acid/H2O to afford α,α‐dibromoketone and 1,2‐diketone derivatives. Diarylalkynes with activating groups provided 1,2‐diketone derivatives as the major products, whereas diarylalkynes with a non‐activating group or alkylarylalkynes gave α,α‐dibromoketone derivatives as the major products. In addition, diarylalkynes with deactivating groups provided 1,2‐dibromoalkenes. The reaction was conducted at

  内部炔烃与二溴异氰尿酸/ H 2 O反应，得到α，α-二溴酮和1,2-二酮衍生物。具有活化基团的二芳基炔烃提供1,2-二酮衍生物作为主要产物，而具有非活化基团的二芳基炔烃或烷基芳基炔烃提供的α，α-二溴酮衍生物为主要产物。此外，带有失活基团的二芳基炔烃可提供1,2-二溴烯烃。该反应在室温下进行，并且在大多数情况下显示出良好的产率。已经基于实验观察和密度泛函理论（DFT）计算提出了反应途径。
• Highly stereo-selective synthesis of (Z)-2,3-diiodo-1,4-diarylbut-2-ene-1,4-diones via oxidative iodination of 1,4-diarylbuta-1,3-diynes
  作者：Raju Singha、Shubhendu Dhara、Jayanta K. Ray

  DOI：10.1039/c3ra44965c

  日期：——

  A novel and highly stereo and regioselective oxidative iodination of 1,4-diarylbuta-1,3-diynes promoted by N-iodosuccinamide results in (Z)-2,3-diiodo-1,4-diarylbut-2-ene-1,4-diones. In the case of NBS, the stereo-selectivity is moderate while NIS gives exclusively Z product. A plausible mechanism for the formation of both E and Z products is also proposed.

  一种新颖且具有高立体和区域选择性的氧化碘化反应，由N-碘代琥珀酰亚胺促进的1,4-二芳基丁a-1,3-二炔，生成(Z)-2,3-二碘-1,4-二芳基丁-2-烯-1,4-二酮。在使用NBS的情况下，立体选择性中等，而NIS则完全生成Z型产物。同时，也提出了形成E和Z产物的可能机制。
• A New Simple Synthesis of Aryl-Substituted 1,4-Diketones
  作者：Alexander V. Kel’in、Oleg G. Kulinkovich

  DOI：10.1055/s-1996-4215

  日期：1996.3

  1,4-Diketones have been prepared by aldol condensation of methyl ketones with α-bromo ketones in the presence of tert-butoxymagnesium or diethylamido magnesium bromide and subsequent rearrangement of the formed 4-bromo-3-hydroxy ketones under the action of triethylamine.

  1,4-二酮可通过在叔丁氧基镁或二乙氨基镁溴化物的存在下，将甲基酮与α-溴酮进行醇醛缩合反应制备，随后在三乙胺的作用下，对形成的4-溴-3-羟基酮进行重排反应。
• Electroluminescent devices
  申请人：——

  公开号：US20040151943A1

  公开（公告）日：2004-08-05

  A compound of formula [I]: X—R  [I] wherein X represents the group: 1 and R is either (i) represented by the formula [II] 2 wherein n is 1 or 2, and the or each R 7 group is independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups; or (ii) is selected from the group consisting of optionally substituted alkyl, hydroxyalkyl, aryl, cyclic hydrocarbon and heterocyclic groups; wherein in each case R 1 -R 6 are each independently selected from the group consisting of hydrogen and halogen atoms, cyano, nitro, mercapto, carbonyl and sulfone groups, and optionally substituted alkyl, haloalkyl, hydroxyalkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylthio, arylthio, ester, siloxy, cyclic hydrocarbon and heterocyclic groups. The compounds are useful as hole-transporting materials in electroluminescence devices.

  一种化合物的化学式为[I]:X-R，其中X代表基团：1，R要么是(i)由式[II]2表示，其中n为1或2，且每个R7基团独立地选择自羟基和卤素原子、氰基、硝基、巯基、羰基和磺酰基，以及可选择取代的烷基、卤代烷基、羟基烷基、芳基、烷氧基、芳氧基、烷基氨基、芳基氨基、烷硫基、芳硫基、酯基、硅氧烷基、环烃和杂环基；或者(ii)选择自可选择取代的烷基、羟基烷基、芳基、环烃和杂环基；在每种情况下，R1-R6各自独立地选择自羟基和卤素原子、氰基、硝基、巯基、羰基和磺酰基，以及可选择取代的烷基、卤代烷基、羟基烷基、芳基、烷氧基、芳氧基、烷基氨基、芳基氨基、烷硫基、芳硫基、酯基、硅氧烷基、环烃和杂环基。该化合物在电致发光器件中作为空穴传输材料有用。
• Lutz,R.F. et al., Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 569 - 573
  作者：Lutz,R.F. et al.

  DOI：——

  日期：——