(R)-1-phenylthiopropan-2-ol | 67253-47-8

• 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)-1-phenylthiopropan-2-ol
• 英文别名: 1-(phenylthio)-2-propanol；2-Propanol, 1-(phenylthio)-, (R)-；(2R)-1-phenylsulfanylpropan-2-ol
• CAS: 67253-47-8
• 化学式: C₉H₁₂OS
• 分子量: 168.26
• InChiKey: LMWDPYSNDDVIAD-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (R)-1-phenylthiopropan-2-ol 在 sodium periodate 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of (-)-Grayanotoxin III

  摘要：

  Total synthesis of(-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI2.

  DOI：

  10.1021/jo00098a009
• 作为产物：
  描述：

  (R)-1-phenylthiopropan-2-yl acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以96%的产率得到(R)-1-phenylthiopropan-2-ol
  参考文献：
  名称：

  Enzymatic kinetic resolution of organochalcogenides in supercritical CO2

  摘要：

  1-(Phenylthio)-, 1-(phenylseleno)- and 1-(phenyltelluro)-propan-2-ol were efficiently resolved by CAL-B in sc-CO2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.073

文献信息

• Enantioselective Cross-Coupling of <i>meso</i>-Epoxides with Aryl Halides
  作者：Yang Zhao、Daniel J. Weix

  DOI：10.1021/jacs.5b01909

  日期：2015.3.11

  The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78–95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal

  首次提出了芳基溴化物与内消旋环氧化物形成反式-β-芳基环烷醇的对映选择性交叉亲电偶联。该反应由(bpy)NiCl 2 和手性二茂钛在还原条件下的组合催化。产率范围为 57% 至 99%，对映体过量为 78-95%。这 30 个例子包括各种官能团（醚、酯、酮、腈、缩酮、三氟甲基、磺酰胺、磺酸酯）、芳基和乙烯基卤化物以及五至七元环。一氧化环辛烯向芳基[3.3.0]双环辛醇的转化强烈暗示了碳自由基的中介作用。
• Asymmetric reduction of ketones by Geotrichum candidum in the presence of AmberliteTM XAD, a solid organic solvent
  作者：Kaoru Nakamura、Mikio Fujii、Yoshiteru Ida

  DOI：10.1039/b005204n

  日期：——

  A hydrophobic polymer, Amberlite™ XAD, was used as material to control the stereochemical course of microbial reductions. In the presence of XAD, simple aliphatic and aromatic ketones were reduced to the corresponding (S)-alcohols in excellent enantiomeric excess (ee) while low enantioselectivities were observed in the absence of the polymer.

  疏水的 聚合物，Amberlite ™ XAD被用作控制微生物减少的立体化学过程的材料。在XAD存在下，简单的脂肪族和芳香族酮类在极佳的对映体过量（ee）下被还原为相应的（S）醇，而在不存在对映体的情况下观察到低对映选择性聚合物。
• A facile chemoenzymatic route to enantiomerically pure oxiranes: building blocks for biologically active compounds
  作者：Ulrich Goergens、Manfred P. Schneider

  DOI：10.1039/c39910001064

  日期：——

  The enantiomerically pure building blocks (R)-and (S)-1–4 were prepared both by enantioselective, enzymatic hydrolysis and by acyl transfer, and subsequently converted into the corresponding enantiomerically pure oxiranes (R)- and (S)-7 and 8.

  对映体纯积木（[R ）-和（小号） - 1 - 4通过对映体选择性，酶水解和通过酰基转移制备两者，并随后转化为相应的对映体纯的环氧乙烷（[R ） -和（小号） - 7和8。
• Production of (R)-1-(1,3-dithian-2-yl)propan-2-ol by microbial reduction
  作者：Rosanna Bernardi、Rosanna Cardillo、Dario Ghiringhelli、Orso Vajna de Pava

  DOI：10.1039/p19870001607

  日期：——

  The reduction of several selected carbonyl compounds with growing cultures of Streptomyces sp., Aspergillus niger, and Geotrichum candidum has been studied. The production of (R)-1-(1,3-dithian-2-yl)propan-2-ol of high enantiomeric purity has been achieved by reduction of dithianylacetone with a Streptomyces sp.

  已经研究了随着链霉菌属，黑曲霉和念珠菌的生长而减少的几种选择的羰基化合物。高对映体纯度的（R）-1-（1,3-二噻-2--2-基）丙-2-醇的生产是通过用链霉菌属的sp还原二噻吩基丙酮来实现的。
• pH DEPENDENT OXIDATION-REDUCTION OF 1-BENZENESULFENYL-2-PROPANONE AND ITS OXIDES BY A MICROORGANISM
  作者：Hiromichi Ohta、Yasuo Kato、Gen-ichi Tsuchihashi

  DOI：10.1246/cl.1986.581

  日期：1986.4.5

  Incubation of 1-benzenesulfenyl-2-propanone with Corynebacterium equi IFO 3730 in a weakly acidic medium afforded (S)-1-benzenesulfenyl-2-propanol. On the contrary, when the cultivation was carried out at pH 8 with the same bacterium, only the (S)-alcohol was transformed into the starting ketone, the (R)-alcohol being recovered intact. The similar enantioselectivities were also observed in the reaction of 1-benzenesulfinyl-2-propanone.

  在弱酸性培养基中，将 1-苯磺酰基-2-丙酮与等球孢杆菌 IFO 3730 培养，可得到 (S)-1-苯磺酰基-2-丙醇。相反，在 pH 值为 8 的条件下用同一细菌进行培养时，只有(S)-醇转化为起始酮，(R)-醇被完整地回收。在 1-苯亚磺酰基-2-丙酮的反应中也观察到了类似的对映选择性。