(R)-1-(4-methylphenyl)thiopropan-2-ol | 404898-26-6

• 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-(4-methylphenyl)thiopropan-2-ol
• 英文别名: 1-(p-tolylthio)propan-2-ol；(2R)-1-(4-methylphenyl)sulfanylpropan-2-ol
• CAS: 404898-26-6
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: FANVFKWSVAZDQV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：

  (R)-1-(4-methylphenyl)thiopropan-2-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以38%的产率得到(R,S_S)-1-(4-methylphenyl)sulfinyl-2-propanol
  参考文献：
  名称：

  Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides

  摘要：

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00434-7
• 作为产物：
  描述：

  (R)-1-(4-methylphenyl)thiopropan-2-yl acetate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 (R)-1-(4-methylphenyl)thiopropan-2-ol
  参考文献：
  名称：

  Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides

  摘要：

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00434-7

文献信息

• Chemoenzymatic Cascades for the Enantioselective Synthesis of β‐Hydroxysulfides Bearing a Stereocentre at the C−O or C−S Bond by Ketoreductases
  作者：Fei Zhao、Kate Lauder、Siyu Liu、James D. Finnigan、Simon B. R. Charnock、Simon J. Charnock、Daniele Castagnolo

  DOI：10.1002/anie.202202363

  日期：2022.8

  Four ketoreductases (KREDs) were identified for the enantioselective synthesis of β-hydroxysulfides. KRED311 and KRED349 catalyse the synthesis of β-hydroxysulfides bearing a stereocentre at the C−O bond with opposite absolute configurations via chemoenzymatic cascades from thiophenols/thiols and α-haloketones/alcohols. KRED253 and KRED384 catalyse the synthesis of β-hydroxysulfides bearing a stereocentre

  鉴定了四种酮还原酶 (KRED) 用于 β-羟基硫化物的对映选择性合成。KRED311 和 KRED349 通过苯硫酚/硫醇和 α-卤代酮/醇的化学酶级联催化合成在 C-O 键处具有立体中心且绝对构型相反的 β-羟基硫化物。KRED253 和 KRED384 通过外消旋 α-硫代醛的动态动力学拆分 (DKR) 催化合成在 C-S 键处具有立体中心并具有相反对映选择性的 β-羟基硫化物。
• Humicola lanuginosa lipase-catalyzed enantioselective resolution of β-hydroxy sulfides: versatile synthons for enantiopure β-hydroxy sulfoxides
  作者：Satwinder Singh、Subodh Kumar、Swapandeep Singh Chimni

  DOI：10.1016/s0957-4166(01)00434-7

  日期：2001.9

  Humicola lanuginosa lipase-catalyzed acylation of beta -hydroxy sulfides provides both the (R)- and (S)-enantiomers in high enantiomeric purity. In two cases the resolved hydroxy sulfides were oxidized to give beta -hydroxy sulfoxides in > 99% e.e. The effect of substituents on enantioselectivity is discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.