1-tosylpropan-2-ol

• 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: 1-tosylpropan-2-ol
• 英文别名: (2R)-1-(4-methylphenyl)sulfonylpropan-2-ol
• 化学式: C₁₀H₁₄O₃S
• 分子量: 214.285
• InChiKey: FKWONTUYTTWYST-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  p-tolyl 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1-tosylpropan-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

• 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
• Catalytic asymmetric hydroboration of heterofunctional allylic substrates: an efficient heterogenized version
  作者：Vanesa Lillo、Elena Fernández、Anna M. Segarra

  DOI：10.1016/j.tetasy.2007.03.031

  日期：2007.5

  The hydroboration of heterofunctional allylic systems with catecholborane (HBcat) using neutral and cationic rhodium complexes modified with P-P and P-N bidentate chiral ligands has been described in order to produce the secondary heteroorgano-boronate ester as a major product with moderate enantioselectivity. The immobilization of cationic chiral rhodium complexes onto clays has beneficial effects on the recyclability and reuse of the catalytic system in particular for the hydroboration of allyl aryl sulfones. (c) 2007 Elsevier Ltd. All rights reserved.
• Lipase-promoted dynamic kinetic resolution of racemic β-hydroxyalkyl sulfones
  作者：Piotr Kiełbasiński、Michał Rachwalski、Marian Mikołajczyk、Marcel A.H. Moelands、Binne Zwanenburg、Floris P.J.T. Rutjes

  DOI：10.1016/j.tetasy.2005.05.005

  日期：2005.6

  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.