trans-(±)-3-(phenylthio)butan-2-ol | 10277-53-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: trans-(±)-3-(phenylthio)butan-2-ol
• 英文别名: threo-3-(Phenylthio)-2-butanol；3-(phenylthio)-2-butanol；threo-3-Phenylmercapto-butanol-2；(2R,3R)-3-phenylsulfanylbutan-2-ol
• CAS: 10277-53-9
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: ZPNZKTJWTXMMEW-RKDXNWHRSA-N

物化性质

• 沸点：
  285.6±23.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(±)-3-(phenylthio)butan-2-ol 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 生成 threo-(R^*,R^*)-phenyl 3-hydroxy-2-butyl sulfone
  参考文献：
  名称：

  Transfer Reactions Involving Boron. VII. The Stereochemistry of Ether Cleavages of Epoxides with Phenylthioborane^1,2

  摘要：

  DOI：

  10.1021/ja00962a022
• 作为产物：
  描述：

  1,2-二甲基环氧乙烷 、 苯硫酚 在 三丁基膦 作用下， 以 水 为溶剂， 反应 12.0h， 以83%的产率得到trans-(±)-3-(phenylthio)butan-2-ol
  参考文献：
  名称：

  三丁基膦在水中促进的环氧化物和氮丙啶的高效开环反应。

  摘要：

  发现三丁基膦是各种环氧化物和氮丙啶与亲核试剂的开环反应的有效促进剂，以在水中以中等至优异的产率产生相应的抗双功能产物。

  DOI：

  10.1021/jo025983s

文献信息

• Catalytic Asymmetric Ring-Opening Reaction of<i>meso</i>-Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium-Titanium-Salen Complex
  作者：Jiangtao Sun、Minghua Yang、Fang Yuan、Xuefeng Jia、Xia Yang、Yi Pan、Chengjian Zhu

  DOI：10.1002/adsc.200800767

  日期：2009.4

  Abstractmagnified imageA chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso‐epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β‐arylseleno alcohols and β‐hydroxy sulfides were obtained in good yields and high enantioselectivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process.
• Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase
  作者：Swapandeep Singh Chimni、Kirandeep Kaur、Neeraj Bala

  DOI：10.1016/j.molcatb.2013.06.006

  日期：2013.12

  Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomers in short reaction time. (C) 2013 Elsevier B.V. All rights reserved.
• Thiol-oxygen cooxidation reactions of cyclopentene, cis- and trans-but-2-ene, norbornene, and norbornadiene
  作者：Athelstan L. J. Beckwith、Rudolf D. Wagner

  DOI：10.1021/jo00331a011

  日期：1981.8
• Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium
  作者：Peng Gao、Peng-Fei Xu、Hongbin Zhai

  DOI：10.1016/j.tetlet.2008.09.004

  日期：2008.11

  A convenient, economical, and practical protocol for borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium has been developed, which has greatly expanded the utility scope of borax in organic synthesis. (C) 2008 Elsevier Ltd. All rights reserved.
• Transfer Reactions Involving Boron. VII. The Stereochemistry of Ether Cleavages of Epoxides with Phenylthioborane^1,2
  作者：Daniel J. Pasto、Charles C. Cumbo、James Fraser

  DOI：10.1021/ja00962a022

  日期：1966.5