1-(4-methylphenylthio)butan-2-ol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(4-methylphenylthio)butan-2-ol
• 英文别名: 1-(4-Methylphenyl)sulfanylbutan-2-ol
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: OMTPIBBVELPTEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  1,2-环氧丁烷 、 4-甲苯硫酚 在 食用色素红色105号 、 氧气 、 lithium diisopropyl amide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以82%的产率得到1-(4-methylphenylthio)butan-2-ol
  参考文献：
  名称：

  环氧化物和硫醇的可见光诱导硫醇加成/有氧氧化级联反应合成β-羟基亚砜

  摘要：

  已经开发了光化学硫醇加成/好氧氧化级联反应。该协议使环氧化物和硫醇的有效氧化偶联能够获得结构上有价值的β-羟基亚砜。广泛的官能团可兼容以获得中等至良好的目标产物产率。机理研究揭示了一个顺序反应途径，包括碱促进硫醇将硫醇加成环氧化物和可见光诱导的硫醚有氧氧化。

  DOI：

  10.1039/d1ob01826d

文献信息

• Convenient preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium into chalcogen-chalcogen bonds. Application in the ring-opening of epoxides
  作者：Jennifer Dowsland、Fiona McKerlie、David J Procter

  DOI：10.1016/s0040-4039(00)00687-0

  日期：2000.6

  Convenient conditions are reported for the preparation of ytterbium(III) chalcogenolate complexes by insertion of ytterbium metal into the chalcogen–chalcogen bond of disulfides, diselenides, and ditellurides. The resulting complexes have been found to transfer arylsulfanyl, -selenanyl, and -telluranyl groups to epoxides in a facile ring-opening reaction. The ytterbium(III) chalcogenolate complexes

  据报道，通过将metal金属插入二硫化物，二硒化物和二碲化物的硫属元素-硫属元素键中，可以方便地制备cha（III）硫属元素化物配合物。已经发现，在容易的开环反应中，所得的络合物将芳基硫烷基，-亚硒基和-四氢呋喃基转移到环氧化物上。Lewis硫氰酸）（III）络合物由于其路易斯酸性性质，似乎在活化环氧化物中起双重作用，并向配位的底物提供亲核试剂。
• Stereo‐ and Regioselective Thiolysis of 1,2‐Epoxides in Water
  作者：Barahman Movassagh、Mohammad Soleiman‐Beigi

  DOI：10.1080/00397910701548100

  日期：2007.9.1
• Rapid, benign, and additive-free thiolysis of epoxides under ultrasonic/aqueous conditions
  作者：Mohammad M. Mojtahedi、Sajad Khalili

  DOI：10.1080/17415993.2014.909814

  日期：2014.7.4

  An environmentally friendly and efficient procedure is developed for ring opening of various epoxides with thiols under non-thermal conditions. Reactions take place by ultrasonic irradiation of the two reactants suspended in an additive-free aqueous medium. Consequently, high-yield formation of various beta-hydroxy sulfides is quickly observed.[GRAPHICS].
• Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides
  作者：Najmedin Azizi、Mahtab Edrisi

  DOI：10.1016/j.tetlet.2015.12.080

  日期：2016.2

  An environmentally benign and rapid thiolysis of epoxides using a biodegradable, choline-based task specific ionic liquid has been developed. The ring opening reaction of aryl and alkyl epoxides proceeded rapidly and afforded the corresponding beta-hydroxysulfides in high yields with excellent regioselectivity. The protocol has the advantages of easy work-up, short reaction times, high yields, and a biodegradable catalyst. (C) 2015 Elsevier Ltd. All rights reserved.
• The Generation of (Samarium) Thiolates from Aryl Thiocyanates and Their Reaction with Epoxides: A Route to β-Hydroxy Sulfides
  作者：Ian W.J. Still、L. James、L.J.P. Martyn

  DOI：10.1080/00032719808006491

  日期：1998.3.1

  This investigation describes the reduction of an aryl thiocyanate with samarium(II) iodide, followed by reaction with various epoxides, to produce beta-hydroxy sulfides. This method of ring opening of epoxides provides a substantial improvement in reaction time and convenience over existing methods while maintaining good regioselectivity and excellent yield.