(2-methoxy-2-phenylethyl)(phenyl)sulfane | 141341-45-9

• 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: (2-methoxy-2-phenylethyl)(phenyl)sulfane
• 英文别名: 2-methoxy-2-phenylethyl phenyl sulfide；1-methoxy-1-phenyl-2-phenylthioethane；1-Methoxy-1-phenyl-2-(phenylthio)-ethan；1-methoxy-2-phenylthio-1-phenyl-ethane；(2-Methoxy-2-phenylethyl)sulfanylbenzene
• CAS: 141341-45-9；51256-31-6
• 化学式: C₁₅H₁₆OS
• 分子量: 244.357
• InChiKey: HFRHZNOQOGRUMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methoxy-2-phenylethyl)(phenyl)sulfane 、 alkaline earth salt of/the/ methylsulfuric acid 以 硝基甲烷 为溶剂， 反应 3.0h， 以90%的产率得到methylphenyl <(α-methoxy)phenylethyl> sulfonium tetrafluoroborate
  参考文献：
  名称：

  Chiral sulfur-reagents for the preparation of optically active epoxides

  摘要：

  Acyclic chiral sulfides which could be easily synthesized in both enantiomeric forms leading to poor yields and/or to racemic epoxides, Eliel's oxathiane reagent was used and proved to provide chiral trans diarylepoxides in high yield (70-80%) and enantiomeric purities up to 70-100%, with no rearrangement problems. It was also found that phase-transfer conditions were the easiest and the most efficient for these reactions.

  DOI：

  10.1016/s0040-4020(01)88764-0
• 作为产物：
  描述：

  N-苯甲酰咪唑 在 lithium aluminium tetrahydride 、 sodium hydride 、 二异丁基氢化铝 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 (2-methoxy-2-phenylethyl)(phenyl)sulfane
  参考文献：
  名称：

  Chiral sulfur-reagents for the preparation of optically active epoxides

  摘要：

  Acyclic chiral sulfides which could be easily synthesized in both enantiomeric forms leading to poor yields and/or to racemic epoxides, Eliel's oxathiane reagent was used and proved to provide chiral trans diarylepoxides in high yield (70-80%) and enantiomeric purities up to 70-100%, with no rearrangement problems. It was also found that phase-transfer conditions were the easiest and the most efficient for these reactions.

  DOI：

  10.1016/s0040-4020(01)88764-0

文献信息

• Metal-free oxysulfenylation of alkenes with 1-(arylthio)pyrrolidine-2,5-diones and alcohols
  作者：Jipan Yu、Chang Gao、Zhixuan Song、Haijun Yang、Hua Fu

  DOI：10.1039/c5ob00252d

  日期：——

  β-Alkoxy sulfides are widely used as versatile building blocks in organic synthesis. Therefore, it is highly desirable to develop a convenient and efficient method for oxysulfenylation of alkenes. In this communication, an easy and efficient metal-free approach to β-alkoxy sulfides has been developed. The protocol uses readily available 1-(arylthio)pyrrolidine-2,5-diones and alcohols as the oxysulfenylating

  β-烷氧基硫化物被广泛用作有机合成中的通用构建基块。因此，非常需要开发一种方便且有效的烯烃的氧亚磺酰基化方法。在这种交流中，已经开发出一种简单有效的无金属方法合成β-烷氧基硫化物。该方案使用容易获得的1-（芳硫基）吡咯烷-2,5-二酮和醇作为氧亚磺酰基化剂，氯仿作为溶剂，不需要配体，添加剂和空气。因此，本方法提供了合成β-烷氧基硫化物的有用策略。
• Photochemical incorporation of protic solvents by open chain olefins
  作者：N. Miyamoto、H. Nozaki

  DOI：10.1016/0040-4020(73)80201-7

  日期：1973.1

  Irradition of methyl styryl sulphoxide dissolved in MeOH, EtOH, or AcOH induces the photochemical polar addition of the solvents to afford the product, PhCH(OR)CH2SOMe, where R is Me, Et, or Ac. By-products are the corresponding sulphides, PhCH(OR)CH2SMe, and methyl styryl sulphide. Similar adducts of protic solvents are produced upon irradiation of certain vinylic sulphides, methyl phenethynyl sulphide

  辐照溶解在MeOH，EtOH或AcOH中的甲基苯乙烯基亚砜会诱导溶剂的光化学极性加成，从而提供产物PhCH（OR）CH 2 SOMe，其中R为Me，Et或Ac。副产物是相应的硫化物，PhCH（OR）CH 2 SMe和甲基苯乙烯基硫化物。质子溶剂的类似加合物在某些乙烯基硫化物的辐照产生，甲基苯乙炔基硫化物，为包括以及适当取代propenylbenzenes ö -anethole，ø -anol和ö -propenylaniline在SOLN。
• Highly Selective Activation of Vinyl C-S Bonds Over Aryl C-S Bonds in the Pd-Catalyzed Coupling of (E)-(β-Trifluoromethyl)vinyldiphenylsulfonium Salts: Preparation of Trifluoromethylated Alkenes and Dienes
  作者：Hao Lin、Xicheng Dong、Yuxue Li、Qilong Shen、Long Lu

  DOI：10.1002/ejoc.201200758

  日期：2012.9

  We describe the Suzuki coupling reaction of (E)-(beta-trifluoromethyl)vinyldiphenylsulfonium salts with arylboronic acid. The highly efficient and selective reaction provides a useful and mild method for the synthesis of trifluoromethylated alkenes and dienes. Subsequent DFT studies showed that the oxidative addition transition state of the vinyl CS bond is much more favorable (11.7 kcal?mol1) than

  我们描述了 (E)-(β-三氟甲基) 乙烯基二苯基锍盐与芳基硼酸的 Suzuki 偶联反应。高效和选择性的反应为合成三氟甲基化烯烃和二烯烃提供了一种有用且温和的方法。随后的 DFT 研究表明，乙烯基 CS 键的氧化加成过渡态比芳基 CS 键更有利（11.7 kcal?mol1）。
• Catalytic Chalcogenylation under Greener Conditions: A Solvent-Free Sulfur- and Seleno-functionalization of Olefins via I₂/DMSO Oxidant System
  作者：André A. Vieira、Juliano B. Azeredo、Marcelo Godoi、Claudio Santi、Eufrânio N. da Silva Júnior、Antonio L. Braga

  DOI：10.1021/jo502621a

  日期：2015.2.20

  Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.