ethyl 2-(benzylthio)-3-phenylpropanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(benzylthio)-3-phenylpropanoate
• 英文别名: ethyl 3-phenyl-2-(benzylthio)propionate；Ethyl 2-benzylsulfanyl-3-phenylpropanoate
• 化学式: C₁₈H₂₀O₂S
• 分子量: 300.422
• InChiKey: AGTWGTVCIZNTCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-(benzylthio)-3-phenylacrylate 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate JosiPhos 、 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、2.5 MPa 条件下， 反应 48.0h， 生成 ethyl 2-(benzylthio)-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric hydrogenation of alkyl(vinyl)thioethers: a promising approach to α-chiral thioethers

  摘要：

  This paper describes the enantio selective hydrogenation of vinylthioethers. We show that thioether derivatives of maleic esters can be hydrogenated with full conversion and up to 60% ee, and that alpha-thioether cinnamic acids can be hydrogenated in 51% ee with modest conversion. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.020

文献信息

• Transition Metal Photoredox Catalysis of Radical Thiol-Ene Reactions
  作者：Elizabeth L. Tyson、Michael S. Ament、Tehshik P. Yoon

  DOI：10.1021/jo3020825

  日期：2013.3.1

  We describe the anti-Markovnikov hydrothiolation of olefins using visible-light-absorbing transition metal photocatalysts. The key thiyl radical intermediates are generated upon quenching of photoexcited Ru*(bpz)32 with a variety of thiols. The adducts of a wide variety of olefins and thiols are formed in excellent yield (73–99%).

  我们描述了使用可见光吸收过渡金属光催化剂对烯烃进行反马尔科夫尼科夫氢硫醇化反应。关键的硫基自由基中间体是在用各种硫醇淬灭光激发的 Ru*(bpz) 3 2后产生的。多种烯烃和硫醇的加合物以优异的产率 (73–99%) 形成。
• 1,2-Thio Group Migration in Rh(II) Carbene Reactions
  作者：Feng Xu、Weifeng Shi、Jianbo Wang

  DOI：10.1021/jo050109v

  日期：2005.5.1

  A series of β-thio group substituted α-diazo carbonyl compounds have been prepared by nucleophilic substitution reactions of thiophenol, thionaphthol, or benzyl mercaptan with β-acetoxy-α-diazo carbonyl compounds. The diazo decomposition of these diazo carbonyl compounds with various transition metal catalysts, including Rh(II) carboxylates and Cu(I) and Cu(II) complexes, has been investigated. It

  通过硫代苯酚，亚硫醇或苄基硫醇与β-乙酰氧基-α-重氮羰基化合物的亲核取代反应已经制备了一系列β-硫基取代的α-重氮羰基化合物。研究了这些重氮羰基化合物在各种过渡金属催化剂（包括羧酸Rh（II）和Cu（I）和Cu（II）配合物）上的重氮分解作用。发现这些化合物的重氮分解产生1，2-硫基迁移产物。在所有情况下均未观察到1,2-氢化物或1,2-芳基迁移产物。
• Asymmetric hydrogenation of alkyl(vinyl)thioethers: a promising approach to α-chiral thioethers
  作者：Alex F. Meindertsma、Michael M. Pollard、Ben L. Feringa、Johannes G. de Vries、Adriaan J. Minnaard

  DOI：10.1016/j.tetasy.2007.11.020

  日期：2007.12

  This paper describes the enantio selective hydrogenation of vinylthioethers. We show that thioether derivatives of maleic esters can be hydrogenated with full conversion and up to 60% ee, and that alpha-thioether cinnamic acids can be hydrogenated in 51% ee with modest conversion. (c) 2007 Elsevier Ltd. All rights reserved.