(R)-3-phenyl-3-(phenylsulfanyl)propan-1-ol | 335383-41-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-3-phenyl-3-(phenylsulfanyl)propan-1-ol
• 英文别名: (R)-3-phenyl-3-(phenylthio)propan-1-ol；(3R)-3-phenyl-3-phenylsulfanylpropan-1-ol
• CAS: 335383-41-0
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: WRZJSJGFVMKXRP-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (3R)-3-phenyl-3-phenylsulfanylpropanal 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (R)-3-phenyl-3-(phenylsulfanyl)propan-1-ol
  参考文献：
  名称：

  The study of biocatalyzed thio-Michael reaction: a greener and multi-gram protocol

  摘要：

  This Letter introduces a new, cheap and green protocol for the thio-Michael reaction. Here we applied three free enzymes such as lipase from pancreas porcine, chymosin and papain and an immobilized one: the Liposyme (R). The reactions were executed at room temperature and resulted in the thio-Michael adduct in good or excellent yields. The protocol describes the use of EtOH as solvent and a less percentage of enzymes, which is in concordance with the green chemistry topics, so we can mention that chymosin and papain were used as biocatalyst in an organic reaction for the first time in this Letter. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.11.047

文献信息

• Rh-Catalyzed Asymmetric Hydrogenation of β-Substituted-β-thio-α,β-unsaturated Esters: Expeditious Access to Chiral Organic Sulfides
  作者：Gang Liu、Zhengyu Han、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/acs.orglett.8b02339

  日期：2018.9.21

  Rh/bifunctional bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydorgenation of both (Z)- and (E)-isomers of β-substituted-β-thio-α,β-unsaturated esters was successfully developed. This new asymmetric catalytic methodology provided highly efficient access to two enantiomers of chiral organic sulfides ethyl β-substituted-β-thio-propanoates with excellent results (up to 99% yield and >99%

  成功开发了Rh /双官能双膦-硫脲配体（ZhaoPhos）催化的β-取代-β-硫代-α，β-不饱和酯的（Z）-和（E）异构体的不对称加氢反应。这种新的不对称催化方法可以高效地获得手性有机硫化物的两种对映异构体，即β-取代-β-硫代丙酸乙酯，具有优异的效果（（Z）底物的收率可达99％，ee大于99％，99％（E）底物的5 ％收率和ee的98％，TON高达5000），它们是有机合成中的重要中间体。
• The study of biocatalyzed thio-Michael reaction: a greener and multi-gram protocol
  作者：Paula V.S. Rizzo、Ligia A. Boarin、Ingridhy O.M. Freitas、Roberto S. Gomes、Adilson Beatriz、Andrelson W. Rinaldi、Nelson Luís C. Domingues

  DOI：10.1016/j.tetlet.2013.11.047

  日期：2014.1

  This Letter introduces a new, cheap and green protocol for the thio-Michael reaction. Here we applied three free enzymes such as lipase from pancreas porcine, chymosin and papain and an immobilized one: the Liposyme (R). The reactions were executed at room temperature and resulted in the thio-Michael adduct in good or excellent yields. The protocol describes the use of EtOH as solvent and a less percentage of enzymes, which is in concordance with the green chemistry topics, so we can mention that chymosin and papain were used as biocatalyst in an organic reaction for the first time in this Letter. (C) 2013 Elsevier Ltd. All rights reserved.