(Z)-1-<(4-Methoxybenzyl)thio>-2-phenylethylene | 155784-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-1-<(4-Methoxybenzyl)thio>-2-phenylethylene
• 英文别名: (Z)-(4-methoxybenzyl)(styryl)sulfane
• CAS: 155784-76-2
• 化学式: C₁₆H₁₆OS
• 分子量: 256.368
• InChiKey: SFVBEYSYJKNULD-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-<(4-Methoxybenzyl)thio>-2-phenylethylene 在 磺酰氯 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 生成 (Z)-2-Phenyl-ethenesulfinic acid 3-phenyl-propyl ester
  参考文献：
  名称：

  Oxidative fragmentations of selected 1-alkenyl sulfoxides. Chemical and spectroscopic evidence for 1-alkenesulfinyl chlorides

  摘要：

  A collection of 1-alkenyl sulfoxides possessing diphenylmethyl, p-methoxybenzyl or 2-(trimethylsilyl)ethyl groups can be converted to 1-alkenesulfinyl chlorides using SO2Cl2. The 1-alkenesulfinyl chlorides were spectroscopically characterized by IR and were chemically captured as their cyclohexyl or 3-phenylpropyl 1-alkenesulfinate esters. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00281-x
• 作为产物：
  描述：

  4-甲氧基苄硫醇 、 苯乙炔 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-1-<(4-Methoxybenzyl)thio>-2-phenylethylene
  参考文献：
  名称：

  Oxidative fragmentations of selected 1-alkenyl sulfoxides. Chemical and spectroscopic evidence for 1-alkenesulfinyl chlorides

  摘要：

  A collection of 1-alkenyl sulfoxides possessing diphenylmethyl, p-methoxybenzyl or 2-(trimethylsilyl)ethyl groups can be converted to 1-alkenesulfinyl chlorides using SO2Cl2. The 1-alkenesulfinyl chlorides were spectroscopically characterized by IR and were chemically captured as their cyclohexyl or 3-phenylpropyl 1-alkenesulfinate esters. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00281-x

文献信息

• CuI-catalyzed regioselective hydrothiolation of alkynes: a thiol-free route to (<i>Z</i>)-β-alkenyl sulfides
  作者：Najmeh Nowrouzi、Mohammad Abbasi、Ensieh Safari、Amin Arman

  DOI：10.1039/d3ob01230a

  日期：——

  A thiol-free procedure for regioselective preparation of (Z)-β-alkenyl sulfides via a three-component reaction of aryl/alkyl halides, phenylacetylene, and potassium isopropylxanthate in the presence of copper iodide as a catalyst in polyethylene glycol is reported. In this study, a xanthate salt is used as an odorless source of sulfur. The reactions proceed in a one-pot and single-step pathway with

  报道了在碘化铜作为催化剂的聚乙二醇存在下，通过芳基/烷基卤化物、苯乙炔和异丙基黄原酸钾的三组分反应，无硫醇区域选择性制备( Z )-β-烯基硫醚的方法。在这项研究中，黄原酸盐被用作无味的硫源。该反应以一锅单步途径进行，形成使用 NMR 数据鉴定的碳酸氢盐中间体，并专门形成Z异构体。
• Synthesis of Vinyl Sulfides by Copper-Catalyzed Decarboxylative C−S Cross-Coupling
  作者：Sadananda Ranjit、Zhongyu Duan、Pengfei Zhang、Xiaogang Liu

  DOI：10.1021/ol101729k

  日期：2010.9.17

  A novel method for the synthesis of vinyl sulfides by the decarboxylative cross-coupling of arylpropiolic acids with thiols using copper(I) salts as catalysts has been developed. In the presence of Cul and Cs2CO3, a variety of thiols reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in good to excellent yields with high stereoselectivity for Z-isomers.
• Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00089a030

  日期：1994.5

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.