1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanone | 10493-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanone
• 英文别名: 4-Benzyloxy-phenacyl-toluol-4-sulfonat；[2-Oxo-2-(4-phenylmethoxyphenyl)ethyl] 4-methylbenzenesulfonate；[2-oxo-2-(4-phenylmethoxyphenyl)ethyl] 4-methylbenzenesulfonate
• CAS: 10493-52-4
• 化学式: C₂₂H₂₀O₅S
• 分子量: 396.464
• InChiKey: IASIGUJRYJGCDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanone 在 甲酸 、 C₃₁H₃₆ClN₂O₂RhS 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以85%的产率得到(R)-1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanol
  参考文献：
  名称：

  Enantioselective synthesis of 1-arylethanediols by rhodium-catalyzed transfer hydrogenation of α-tosyloxyarylketones

  摘要：

  Catalytic transfer hydrogenation of alpha-tosyloxyarylketones mediated by a chiral rhodium complex using an azeotropic mixture of formic acid/triethylamine afforded the corresponding 1-arylethanediol monotosylates in excellent yield with high enantioselectivity.

  DOI：

  10.1007/s00706-008-0009-2
• 作为产物：
  描述：

  4-苯甲氧基苯乙酮 、 羟基甲苯磺酰碘苯 以 乙腈 为溶剂， 以86%的产率得到1-(4-benzyloxyphenyl)-2-(p-tolylsulfonyloxy)ethanone
  参考文献：
  名称：

  Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine

  摘要：

  Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of (beta-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.046

文献信息

• WO2008/54155
  申请人：——

  公开号：——

  公开（公告）日：——
• Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine
  作者：Do-Min Lee、Jong-Cheol Lee、Nakcheol Jeong、Kee-In Lee

  DOI：10.1016/j.tetasy.2007.10.046

  日期：2007.11

  Catalytic transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives leads to efficient synthesis of (beta-adrenergic agonists, (R)-tembamide, (R)-aegeline, (R)-octopamine, and (R)-denopamine. (c) 2007 Elsevier Ltd. All rights reserved.
• METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE 2-SULFONYLOXY-1-PHENYLETHANOL DERIVATIVES
  申请人：Lee Kee-In

  公开号：US20100063317A1

  公开（公告）日：2010-03-11

  Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an α-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.
• US8044245B2
  申请人：——

  公开号：US8044245B2

  公开（公告）日：2011-10-25
• [EN] METHOD FOR THE PREPARATION OF OPTICALLY ACTIVE 2-SULFONYLOXY-1-PHENYLETHANOL DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS 2-SULFONYLOXY-1-PHÉNYLÉTHANOL OPTIQUEMENT ACTIFS
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2008054155A1

  公开（公告）日：2008-05-08

  [EN] Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an a-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.
  [FR] L'invention concerne un dérivé 2-sulfonyloxy-1-phényléthanol optiquement actif de formule (II) qui peut être préparé facilement et de manière sélective par le procédé de la présente invention en utilisant une réduction asymétrique d'un composé ¥á-sulfonyloxy acétophénone avec un catalyseur au rhodium ayant un groupe pentaméthylcyclopentadiényle et un donneur d'hydrogène, et le composé de formule (II) obtenu par le procédé de l'invention présente une valeur e.e. (excès énantiomérique) supérieure à celle des produits dans les procédés classiques.