(S)-1-(furan-2-yl)-2-(phenylsulfonyl)ethanol | 349487-03-2

• 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: (S)-1-(furan-2-yl)-2-(phenylsulfonyl)ethanol
• 英文别名: (1S)-2-(benzenesulfonyl)-1-(furan-2-yl)ethanol
• CAS: 349487-03-2
• 化学式: C₁₂H₁₂O₄S
• 分子量: 252.291
• InChiKey: OGLBNCNPGQGGAO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  75.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (S)-1-(furan-2-yl)-2-(phenylsulfonyl)ethanol 生成
  参考文献：
  名称：

  Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata

  摘要：

  beta -Keto sulfones bearing bulky groups are reduced with high enantioselectivities to the corresponding optically active beta -hydroxy sulfones by the fungus Curvularia lunata CECT 2130; the cells can be re-used without loss of their catalytic activity. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00048-9
• 作为产物：
  描述：

  2-(苯磺酰基)-1-(呋喃-2-基)乙酮 在 Culvularia lunata 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 反应 7.0h， 以91%的产率得到(S)-1-(furan-2-yl)-2-(phenylsulfonyl)ethanol
  参考文献：
  名称：

  Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata

  摘要：

  beta -Keto sulfones bearing bulky groups are reduced with high enantioselectivities to the corresponding optically active beta -hydroxy sulfones by the fungus Curvularia lunata CECT 2130; the cells can be re-used without loss of their catalytic activity. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00048-9

文献信息

• Efficient synthesis of chiral β-hydroxy sulfones <i>via</i> iridium-catalyzed hydrogenation
  作者：Lin Tao、Congcong Yin、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1039/c8ob02923g

  日期：——

  A highly efficient Ir/f-Amphol-catalyzed asymmetric hydrogenation of prochiral β-keto sulfones was successfully developed to prepare a series of chiral β-hydroxy sulfones with good to excellent results (62%–>99% conversions, 35%–99% yields and 86%–>99% ee). Our Ir/f-Amphol L4 catalytic system exhibited very high activity; the gram-scale asymmetric hydrogenation was performed well with just 0.005 mol%

  成功开发了一种高效的Ir / f-Amphol催化的前手性β-酮砜的不对称氢化反应，制备了一系列手性β-羟基砜，具有良好至优异的效果（62％–> 99％转化率，35％–99％收率和86％-> 99％ee）。我们的Ir / f-Amphol L4催化体系表现出很高的活性；仅用0.005 mol％的催化剂负载量（S / C = 20 000）就很好地进行了克级不对称氢化，以提供具有> 99％的转化率，99％的收率和93％的ee的所需产物2a。
• Enantioselective reduction of β-keto sulfones using the NaBH4/Me3SiCl system catalyzed by polymer-supported chiral sulfonamide
  作者：Gang Zhao、Jian-bing Hu、Zhan-shan Qian、Wei-xing Yin

  DOI：10.1016/s0957-4166(02)00546-3

  日期：2002.10

  In the presence of 25 mol% of polymer-supported chiral sulfonamide, a variety of beta-keto sulfones can be reduced into the corresponding beta-hydroxy sulfones in excellent yields and with high enantioselectivities using the reducing system of NaBH4/Me3SiCl. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric Hydrogenation of β-Keto Sulfonamides and β-Keto Sulfones with a Chiral Cationic Ruthenium Diamine Catalyst
  作者：Xiao-Fei Huang、Shao-Yun Zhang、Zhi-Cong Geng、Chun-Yuen Kwok、Peng Liu、Hai-Yan Li、Xing-Wang Wang

  DOI：10.1002/adsc.201300331

  日期：2013.10.11

  AbstractOptically active β‐hydroxy sulfonamides and β‐hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of β‐keto sulfonamides and β‐keto sulfones has been developed using the phosphine‐free chiral ruthenium complex Ru(OTf)(TsDPEN)(η6‐p‐cymene) as the catalyst, to afford the corresponding β‐hydroxy sulfonamides and β‐hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic β‐keto sulfonamides and β‐keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic β‐hydroxy sulfonamides and β‐hydroxy sulfones in good yields with excellent enantio‐ and diastereoselectivities.magnified image
• Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata
  作者：Vicente Gotor、Francisca Rebolledo、Ramón Liz

  DOI：10.1016/s0957-4166(01)00048-9

  日期：2001.3

  beta -Keto sulfones bearing bulky groups are reduced with high enantioselectivities to the corresponding optically active beta -hydroxy sulfones by the fungus Curvularia lunata CECT 2130; the cells can be re-used without loss of their catalytic activity. (C) 2001 Published by Elsevier Science Ltd.