(E)-1-(phenylselenenyl)-2-(4-methylphenyl)ethene | 60466-41-3

• 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)-1-(phenylselenenyl)-2-(4-methylphenyl)ethene
• 英文别名: (E)-1-methyl-4-(2-phenylselanylvinyl)-benzene；(E)-2-(4-methylphenyl)vinyl phenyl selenide；(E)-(4-methylstyryl)(phenyl)selenide；(E)-(4-methylstyryl)(phenyl)selane；1-methyl-4-[(E)-2-phenylselanylethenyl]benzene
• CAS: 60466-41-3
• 化学式: C₁₅H₁₄Se
• 分子量: 273.236
• InChiKey: UXLGNDAOQQBVBD-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：

  (E)-1-(phenylselenenyl)-2-(4-methylphenyl)ethene 在 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以67%的产率得到(E)-2-(4-methylphenyl)vinyl phenyl selenone
  参考文献：
  名称：

  Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(−)-bornyl malonate

  摘要：

  The reaction of vinyl selenones with di-(-)-bornyl malonate and sodium hydride occurred with low diastereoselectivity and afforded a mixture of two diastereomeric cyclopropane derivatives in comparable yields. These, however, could be easily separated by chromatography. Removal of the bornyl group afforded highly enantiomerically enriched cyclopropanes. An example of the simple conversions of these cyclopropanes into useful cyclopropane alpha-amino acids is also illustrated. The syntheses of several vinyl selenides and selenones are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.05.019
• 作为产物：
  描述：

  对甲基肉桂酸 在 N,N-二甲基丙烯基脲 、 lithium acetate 作用下， 以 水 、 乙腈 为溶剂， 反应 12.08h， 生成 (E)-1-(phenylselenenyl)-2-(4-methylphenyl)ethene
  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

• Lanthanum-catalyzed stereoselective synthesis of vinyl sulfides and selenides
  作者：V. Prakash Reddy、K. Swapna、A. Vijay Kumar、K. Rama Rao

  DOI：10.1016/j.tetlet.2009.11.004

  日期：2010.1

  oxide/TMEDA-catalyzed cross-coupling of vinyl halides with thiols/diphenyl diselenide in anhydrous DMSO and KOH is reported. Utilizing this protocol various vinyl sulfides and selenides were synthesized in excellent yields with retention of the stereochemistry. The catalyst was recyclable.

  据报道，在无水DMSO和KOH中，氧化镧/ TMEDA催化卤代乙烯与硫醇/二苯基二硒化物的交叉偶联。利用该方案，以优异的产率合成了各种乙烯基硫化物和硒化物，并保留了立体化学。该催化剂是可回收的。
• Copper nano-catalyst: sustainable phenyl-selenylation of aryl iodides and vinyl bromides in water under ligand free conditions
  作者：Amit Saha、Debasree Saha、Brindaban C. Ranu

  DOI：10.1039/b819137a

  日期：——

  A simple and efficient procedure for the synthesis of aryl- and vinyl-selenides has been developed by a copper nanoparticle catalysed reaction of aryl iodide/vinyl bromide with diphenyl diselenide in the presence of zinc in water. (E)-Vinyl bromides produce (E)-vinyl selenides stereoselectively, whereas (Z)-vinyl bromides provide mixtures of (E) and (Z) isomers. The catalyst was recycled.

  通过铜纳米粒子催化的反应，在水中的锌存在下，已开发出一种合成芳基和乙烯基硒化物的简单高效过程。这一过程利用芳基碘化物/乙烯基溴化物与二苯基二硒化物的反应。(E)-乙烯基溴化物有选择性地生成(E)-乙烯基硒化物，而(Z)-乙烯基溴化物则生成(E)和(Z)异构体的混合物。催化剂可以回收利用。
• 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。
• Copper-catalyzed Stereoselective Synthesis of Vinyl Selenides under Ligand-free Conditions
  作者：Vutukuri Prakash Reddy、Akkilagunta Vijay Kumar、Kakulapati Rama Rao

  DOI：10.1246/cl.2010.212

  日期：2010.3.5

  A mild and efficient protocol for the stereoselective synthesis of vinyl selenides catalyzed by CuO nanoparticles as recyclable catalyst under ligand-free conditions is reported. This methodology results in the synthesis of a variety of vinyl selenides in excellent yields with retention of stereochemistry.

  报道了一种在无配体条件下由 CuO 纳米粒子作为可回收催化剂催化立体选择性合成乙烯基硒化物的温和有效的方案。这种方法导致以极好的收率合成各种乙烯基硒化物，同时保留了立体化学。
• Stereoselective Synthesis of Vinyl Selenides by Coupling of Vinyl Bromides with Diorgano Diselenides Catalyzed by Copper(I) in [Bmim]BF₄
  作者：Weiliang Bao、Dezhi Chang

  DOI：10.1055/s-2006-947320

  日期：2006.7

  The CuI/L-proline-catalyzed zinc-promoted coupling reaction of vinyl bromides with diaryl diselenides or dialkyl diselenides readily occurred at 110 °C in [Bmim]BF 4 to give the corresponding vinyl selenides in good to excellent yields. The recyclable catalyst system offered a convenient, stereoselective and versatile method for the synthesis of vinyl selenides.

  CuI/L-脯氨酸催化的锌促进乙烯基溴化物与二芳基二硒化物或二烷基二硒化物的偶联反应在 110°C 下在 [Bmim]BF 4 中很容易发生，以良好到极好的产率得到相应的乙烯基硒化物。可回收的催化剂体系为合成乙烯基硒化物提供了一种方便、立体选择性和通用的方法。