(E)-(styryl)(4-chloro-phenyl)selenide | 175023-75-3

• 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: (E)-(styryl)(4-chloro-phenyl)selenide
• 英文别名: (E)-styryl(4-chlorophenyl)selenide；4-chlorophenyl (E)-styryl selenide；E-(Ph)CHCH((C6H4Cl-p)Se)；1-chloro-4-[(E)-2-phenylethenyl]selanylbenzene
• CAS: 175023-75-3
• 化学式: C₁₄H₁₁ClSe
• 分子量: 293.654
• InChiKey: MTLTUHJFXVMCMA-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  乙烯双(三苯基磷)铂 、 (E)-(styryl)(4-chloro-phenyl)selenide 以 氘代苯 为溶剂， 生成 trans-Pt[(E)-C(H)C(H)(Ph))](Se(C6H4Cl-p))(PPh3)2
  参考文献：
  名称：

  无环乙烯基硒化物氧化加成到M（0）络合物的第一个确定性例子

  摘要：

  The principle of C–S bond activation of acyclic vinlyl sulfide by platinum(0)-complex was applied to the C–Se bond fission of vinyl selenide. The substrate possessing Ph and ArSe (Ar = C6H4Cl-p) substituents at the β-carbon successfully reacted with Pt(0)-complex at 25 °C to produce the vinyl platinum in good yield and its structure was unambiguously determined by X-ray crystallographic analysis. When

  DOI：

  10.1016/j.jorganchem.2005.12.058
• 作为产物：
  描述：

  对氯碘苯 在 N,N-二甲基丙烯基脲 、 2,2'-联吡啶 、 selenium 、 copper(l) iodide 、 sodium carbonate 、 magnesium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-(styryl)(4-chloro-phenyl)selenide
  参考文献：
  名称：

  Transition-metal free synthesis of diaryl vinyl selenides: a simple synthetic approach with high selectivity

  摘要：

  A simple, highly efficient synthetic protocol is developed for the synthesis of unsymmetrical diaryl vinyl selenides from diaryldiselenide and beta-bromo styrene under transition-metal free conditions in N,N'dimethyl propylene urea and 130 degrees C to afford high yields and excellent selectivities. This method provides a new strategy to fabricate a wide variety of important substituted molecular skeletons and an alternative to conventionally used metal salts, additives, and ligands. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.011

文献信息

• Glycerol as a promoting medium for cross-coupling reactions of diaryl diselenides with vinyl bromides
  作者：Loren C. Gonçalves、Gabriela F. Fiss、Gelson Perin、Diego Alves、Raquel G. Jacob、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2010.10.107

  日期：2010.12

  herein the use of glycerol as a novel solvent in the cross-coupling reaction of diaryl diselenides with vinyl bromides catalyzed by CuI. This cross-coupling reaction was performed with diaryl diselenides and (Z)- or (E)-vinyl bromides bearing electron-withdrawing and electron-donating groups, affording the corresponding vinyl selenides in good to excellent yields. The mixture glycerol/catalyst can be

  我们在本文中描述了甘油在二芳基二硒化物与CuI催化的乙烯基溴的交叉偶联反应中作为新型溶剂的用途。该交叉偶联反应是用带有吸电子和给电子基团的二芳基二硒化物和（Z）-或（E）-乙烯基溴化物进行的，从而以良好或优异的产率提供了相应的乙烯基硒化物。甘油/催化剂的混合物可直接用于进一步的交叉偶联反应。
• A highly efficient and reusable MCM-41-immobilized bipyridine copper(<scp>i</scp>) catalyst for the C–Se coupling of organoboronic acids with diaryl diselenides
  作者：Hong Zhao、Yuanyuan Jiang、Qiurong Chen、Mingzhong Cai

  DOI：10.1039/c4nj01687d

  日期：——

  A highly efficient MCM-41-immobilized bipyridine copper(I) complex [MCM-41-bpy-CuI] was prepared from 4,4′-bis[3-(triethoxysilyl)propylaminomethyl]-2,2′-bipyridine via immobilization on the mesoporous material MCM-41, followed by reaction with CuI. In the presence of 5 mol% MCM-41-bpy-CuI, the cross-coupling reaction of organoboronic acids with diaryl diselenides proceeded smoothly in DMSO/H2O (2/1)

  A高效MCM-41固定联吡啶铜（我）络合物[MCM-41联吡啶翠]从4,4'-双[3-（三乙氧基硅基）丙基氨基] -2,2'-联吡啶制备通过固定上介孔材料MCM-41，然后与CuI反应。在5 mol％MCM-41-bpy-CuI的存在下，有机硼酸与二芳基二硒化物的交叉偶联反应在DMSO / H 2 O（2/1）中于110°C的空气中顺利进行，得到了多种二有机基硒化物，收率好至极好。可以通过简单过滤反应溶液来回收和再循环这种多相铜催化剂，并在不降低活性的情况下，至少进行了10次连续试验。
• Stereoselective synthesis of (E)-vinylic selenides via hydrozirconation of alk-1-ynes
  作者：Xian Huang、Liu-Sheng Zhu

  DOI：10.1039/p19960000767

  日期：——

  Hydrozirconation of alk-1-ynes 1 gives organozirconium(IV) complexes 2, which are trapped with arylselenenyl bromides to afford (E)-vinylic selenides 3 in high yields.

  烷-1-炔氢化锆反应生成有机锆（IV）络合物 2，与芳基硒溴化物反应生成(E)-乙烯基硒化物 3，产量很高。
• Hypervalent Iodine in Synthesis 44: Stereoselective Synthesis of Vinylic Selenides by the Reaction of Sodium Selenolates with Vinyl (Phenyl) Iodonium Salts
  作者：Jie Yan、Zhen-Chu Chen

  DOI：10.1080/00397910008087118

  日期：2000.3

  Abstract Vinylic selenides have been prepared stereoselectively by the reaction of sodium selenolates with vinyl(phenyl)iodonium salts with retention or inversion of the configurations.

  摘要 通过硒酸钠与乙烯基（苯基）碘鎓盐反应，保留或反转构型，可以立体选择性地制备乙烯基硒化物。
• Stereoselective synthesis of (E)-Vinylic selenides
  作者：Xian Huang、Liu-Sheng Zhu

  DOI：10.1080/00397919608086739

  日期：1996.2

  1-Alkynes react with Cp(2)Zr(H) Cl (Cp = eta(5)-C5H5) giving organozirconium(IV) complexes, which are trapped with diaryl diselenides to afford (E)-vinylic selenides.