(E)-(styryl)(4-methyl-phenyl)selenide | 183056-31-7

• 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-methyl-phenyl)selenide
• 英文别名: 1(E)-(styryl)(4-methylphenyl)selenide；4-methylphenyl (E)-styryl selenide；1-methyl-4-[(E)-2-phenylethenyl]selanylbenzene
• CAS: 183056-31-7
• 化学式: C₁₅H₁₄Se
• 分子量: 273.236
• InChiKey: DOWRGGQNSSHFES-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  苯基溴化镁 、 (E)-(styryl)(4-methyl-phenyl)selenide 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以83%的产率得到反式-1,2-二苯乙烯
  参考文献：
  名称：

  通过顺序交叉偶联反应立体选择性合成 (E)-1,2-二取代乙烯

  摘要：

  摘要 在 NiCl2(PPh3)2 催化剂存在下，格氏试剂与 (E)-1-卤代-2-芳基硒代乙烯反应形成两个 CC 键，提供了立体选择性合成 (E)-1,2-二取代乙烯高产。

  DOI：

  10.1080/00397919708004803
• 作为产物：
  描述：

  肉桂酸 在 N,N-二甲基丙烯基脲 、 lithium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 6.08h， 生成 (E)-(styryl)(4-methyl-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。
• 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。
• A Stereoselective Synthesis of (E)-Arylvinyl Selenides via Coupling of (E)-Vinylseleno Zirconocenes and Diaryliodonium Salts
  作者：Jun-Hua Wang、Qing Xu、Xian Huang

  DOI：10.1039/a905291g

  日期：——

  (E)-Arylvinyl selenides are prepared by coupling of (E)-vinylseleno zirconocenes and diaryliodonium salts.

  (E)-Arylvinyl selenides 是通过 (E)-vinylseleno 锆烯和二月桂碘鎓盐偶联制备的。
• Stereoselective synthesis of (E)-vinylic selenides by palladium catalyzed cross-coupling reactions
  作者：Xian Huang、Liu-Sheng Zhu

  DOI：10.1016/0022-328x(96)06373-5

  日期：1996.10

  Hydrozirconation of arylselenoethynes gives zirconium (IV) complexes 3, which are cross-coupled with aryl halides in the presence of tetrakis (triphenylphosphine) palladium catalyst to afford (E)-vinylic selenides 5 in high yield.

  芳基硒乙炔的加氢锆化得到锆（IV）配合物3，其在四（三苯基膦）钯催化剂存在下与芳基卤化物交联，从而以高收率提供（E）-乙烯基硒化物5。