S-phenyl (E)-4-phenylbut-3-enethioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-phenyl (E)-4-phenylbut-3-enethioate
• 化学式: C₁₆H₁₄OS
• 分子量: 254.353
• InChiKey: UJQNRVHVUPTGGD-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-phenyl (E)-4-phenylbut-3-enethioate 在 双(三-o-甲苯磷)钯(0) 作用下， 以 对二甲苯 为溶剂， 以81%的产率得到(E)-1-phenyl-3-(phenylthio)propene
  参考文献：
  名称：

  Palladium- and Nickel-Catalyzed Decarbonylative C–S Coupling to Convert Thioesters to Thioethers

  摘要：

  This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

  DOI：

  10.1021/acs.orglett.7b03305
• 作为产物：
  描述：

  苯乙醛 在 N-甲基吗啉 、 1-羟基苯并三唑 作用下， 以 乙酸乙酯 为溶剂， 反应 16.08h， 生成 S-phenyl (E)-4-phenylbut-3-enethioate
  参考文献：
  名称：

  在有机催化对映选择性迈克尔反应中控制乙烯基酮醇的α/γ反应性

  摘要：

  布朗斯台德碱/氢键双功能催化能够实现β，γ-不饱和酮与硝基烯烃的第一个区域，非对映和对映选择性直接Michael反应。方胺取代的叔胺催化广泛的β，γ-不饱和酮反应仅在α位进行，从而产生了两个连续的叔碳立体中心的非对映异构体比率最高> 20：1的加合物，并且对映选择性通常在90–98％ee范围内。

  DOI：

  10.1002/anie.201703764

文献信息

• Highly Regioselective Thiocarbonylation of Allylic Alcohols with Thiols and Carbon Monoxide Catalyzed by Palladium Complexes:  A New and Efficient Route to β,γ-Unsaturated Thioesters
  作者：Wen-Jing Xiao、Howard Alper

  DOI：10.1021/jo9812328

  日期：1998.10.1

  The reaction of allylic alcohols with thiols and carbon monoxide in the presence of catalytic quantities of Pd(OAc)(2) (3 mol %), triphenylphosphine (12 mol %), and p-TsOH (5 mol %) leads to a novel thiocarbonylation to afford beta,gamma-unsaturated thioesters in good to excellent yields. Other palladium catalyst systems such as Pd-2(dba)(3). CHCl3-PPh3-p-TsOH, Pd(PPh3)(4)-p-TsOH, and Pd(OAc)(2)-dppb-p-TsOH are also effective for this transformation. The thiocarbonylation reaction is believed to proceed via a allylpalladium intermediate. The reaction occurs highly regioselectively at the least hindered allylic terminal carbon of the substrate to give the products. This new carbonylation procedure was readily applied to a variety of allylic alcohols and both aromatic and aliphatic thiols.
• Controlling the α/γ-Reactivity of Vinylogous Ketone Enolates in Organocatalytic Enantioselective Michael Reactions
  作者：Igor Iriarte、Olatz Olaizola、Silvia Vera、Iñaki Gamboa、Mikel Oiarbide、Claudio Palomo

  DOI：10.1002/anie.201703764

  日期：2017.7.17

  The first regio-, diastereo-, and enantioselective direct Michael reaction of β,γ-unsaturated ketones with nitroolefins is enabled by Brønsted base/hydrogen-bonding bifunctional catalysis. A squaramide-substituted tertiary amine catalyzes the reaction of a broad range of β,γ-unsaturated ketones to proceed at the α-site exclusively, giving rise to adducts with two consecutive tertiary carbon stereocenters

  布朗斯台德碱/氢键双功能催化能够实现β，γ-不饱和酮与硝基烯烃的第一个区域，非对映和对映选择性直接Michael反应。方胺取代的叔胺催化广泛的β，γ-不饱和酮反应仅在α位进行，从而产生了两个连续的叔碳立体中心的非对映异构体比率最高> 20：1的加合物，并且对映选择性通常在90–98％ee范围内。
• Palladium- and Nickel-Catalyzed Decarbonylative C–S Coupling to Convert Thioesters to Thioethers
  作者：Naoko Ichiishi、Christian A. Malapit、Łukasz Woźniak、Melanie S. Sanford

  DOI：10.1021/acs.orglett.7b03305

  日期：2018.1.5

  This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.