(R)-1-(phenylsulfonyl)-propan-2-ol | 102838-84-6

• 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: (R)-1-(phenylsulfonyl)-propan-2-ol
• 英文别名: (R)-1-(phenylsulphonyl)propan-2-ol；(R)-1-(phenylsulfonyl)-2-propanol；(R)-1-(phenylsulfonyl)propan-2-ol；(2R)-1-(benzenesulfonyl)propan-2-ol
• CAS: 102838-84-6
• 化学式: C₉H₁₂O₃S
• 分子量: 200.258
• InChiKey: ADGDGIOFSAGJEX-MRVPVSSYSA-N

物化性质

• 沸点：
  388.5±34.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-(phenylsulfonyl)-propan-2-ol 在 正丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Enantioselective hydrogenation of β-keto sulfones with chiral Ru(II)-catalysts: synthesis of enantiomerically pure butenolides and γ-butyrolactones

  摘要：

  A series of beta-hydroxy sulfones were synthesized with high enantioselectivities via a new enantioselective ruthenium-catalyzed hydrogenation using MeO-BIPHEP as a ligand. Some beta-hydroxy sulfones were used in the synthesis of optically active butenolides and gamma-butyrolactones with high yields and enantioselectivities over 95%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00113-5
• 作为产物：
  描述：

  phenyl 1-(2-acetoxy)propyl sulfone 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到(R)-1-(phenylsulfonyl)-propan-2-ol
  参考文献：
  名称：

  Lipase-promoted dynamic kinetic resolution of racemic β-hydroxyalkyl sulfones

  摘要：

  A series of racemic beta aryl-hydroxyalkyl sulfones have been successfully transformed into the corresponding optically active O-acetyl derivatives in high yields (up to 80%) with enantiomeric excesses more than 99% using a dynamic kinetic resolution procedure, in which a lipase-promoted kinetic resolution is combined with a concomitant ruthenium-catalysed racemization of the substrates. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.005

文献信息

• Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
  作者：Abraham L. Moure、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1039/c1cc11949d

  日期：——

  The alpha,beta-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate beta-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B(2)(pin)(2)] catalyzed by nonracemic Cu(I)-diphosphine complexes to provide, upon subsequent oxidation, beta-hydroxy sulfones in good yields and high enantiocontrol.

  α，β-不饱和砜是催化不对称共轭β-硼酸酯化反应中合适的活化烯烃。这些底物通过非外消旋的Cu（I）-二膦配合物催化双（pinacolato）diboron [B（2）（pin）（2）]的平滑共轭加成，从而在随后的氧化反应中，以高收率和高收率提供β-羟基砜对映体控制。
• Efficient synthesis of an apremilast precursor and chiral β-hydroxy sulfones <i>via</i> ketoreductase-catalyzed asymmetric reduction
  作者：Jiyang Guo、Xiao Gao、Dong Qian、Huibin Wang、Xian Jia、Wenhe Zhang、Bin Qin、Song You

  DOI：10.1039/d1ob02485j

  日期：——

  substrate loading. Furthermore, we investigated the substrate scope of β-keto sulfones by using LfSDR1-V186A/E141I and CgKR1-F92I to produce both enantiomers of the corresponding β-hydroxy sulfones, with good-to-excellent conversion (up to >99%) and enantioselectivity (up to 99.9% ee) being obtained in most cases. Finally, the gram-scale synthesis of (R)-2a was performed by employing the crude enzyme of

  酮还原酶（KRED）催化前手性酮的不对称还原是合成手性醇的一种有吸引力的方法。在此，鉴定出具有互补立体偏好的两个 KRED LfSDR1-V186A/E141I 和 CgKR1-F92I 用于还原阿普斯特前手性酮中间体1a 。 LfSDR1-V186A/E141I表现出>99%转化率和99.2% ee，在50 g L -1底物负载量下产生阿普斯特手性醇中间体(( R ) -2a )。此外，我们通过使用 LfSDR1-V186A/E141I 和 CgKR1-F92I 来研究 β-酮基砜的底物范围，以产生相应 β-羟基砜的两种对映体，具有良好到优异的转化率（高达 >99%）和大多数情况下可获得对映选择性（高达 99.9% ee）。最后，利用LfSDR1-V186A/E141I的粗酶和BsGDH进行克级合成( R ) -2a ，得到所需的对映体，转化率>99%，分离收率85.9%，ee 99.2%。本研究提出了合成手性
• 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。
• General synthesis of chiral β-hydroxy sulfones via enantioselective ruthenium-catalyzed hydrogenation
  作者：P Bertus、P Phansavath、V Ratovelomanana-Vidal、J.-P Genêt、A.R Touati、T Homri、B.Ben Hassine

  DOI：10.1016/s0040-4039(99)00453-0

  日期：1999.4

  A new ruthenium-promoted hydrogenation of β-keto sulfones using MeO-BIPHEP as ligand is reported with complete conversions and enantiomeric excesses over 95%.

  据报道，使用MeO-BIPHEP作为配体，钌促进了β-酮砜的氢化反应，完全转化，对映体过量超过95％。