(4-fluorophenyl)(p-tolyl)methanol

• 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: (4-fluorophenyl)(p-tolyl)methanol
• 英文别名: (S)-(4-fluorophenyl)-(4-methylphenyl)methanol
• 化学式: C₁₄H₁₃FO
• 分子量: 216.255
• InChiKey: RUPDLRIDZKCKHV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氟苯硼酸 、 对甲基苯甲醛 在 diethylzinc 、 (1R,2R)-N-diphenylphosphinothioyl-1,2-diphenyl-N'-propan-2-ylethane-1,2-diamine 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 36.5h， 以91%的产率得到(4-fluorophenyl)(p-tolyl)methanol
  参考文献：
  名称：

  Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols

  摘要：

  In this investigation, chiral thiophosphoramide 3d was easily prepared from chiral (1R,2R)-1,2-diphenylethylenediamine and then applied as an efficient chiral ligand in the catalytic asymmetric arylation reactions of various aromatic aldehydes. The corresponding diarylmethanol products were produced with good to excellent yields (up to 98%) and enantioselectivities (up to 94%). The recovery of chiral ligand 3d could be as high as 96%. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.011

文献信息

• Electronic Effect‐Guided Rational Design of <i>Candida antarctica</i> Lipase B for Kinetic Resolution Towards Diarylmethanols
  作者：Dan‐Yang Li、Yu‐Jiao Lou、Jian Xu、Xiao‐Yang Chen、Xian‐Fu Lin、Qi Wu

  DOI：10.1002/adsc.202001367

  日期：2021.3.29

  design strategy to enhance the enantioselectivity of Candida antarctica lipase B (CALB) mutants towards bulky pyridyl(phenyl)methanols. Compared to W104A mutant previously reported with reversed S‐stereoselectivity toward sec‐alcohols, three mutants (W104C, W104S and W104T) displayed significant improvement of S‐enantioselectivity in the kinetic resolution (KR) of various phenyl pyridyl methyl acetates due

  本文中，我们开发了一种以电子效应为指导的合理设计策略，以增强南极假丝酵母脂肪酶B（CALB）突变体对大体积吡啶基（苯基）甲醇的对映选择性。相比W104A突变先前具有相反报道小号朝向-stereoselectivity秒-醇，三个突变体（W104C，W104S和W104T）显示的显著改善小号由于吡啶基和极性残基之间电子效应的增强，各种苯基吡啶基乙酸甲酯的动力学拆分（KR）的对映选择性。当突变CALB的立体特异性口袋周围的其他残基（例如T42A，S47A，A281S或A281C）时，也观察到了电子效应，可用于操纵立体选择性。以良好的收率和ee值获得了一系列大体积的吡啶基（苯基）甲醇，包括S-（4-氯苯基）（吡啶-2-基）甲醇（S- CPMA）（贝托斯汀的中间体）。
• Chiral thiophosphoramide catalyzed asymmetric aryl transfer reactions for the synthesis of functional diarylmethanols
  作者：Yabai Wang、Hua Zong、Huayin Huang、Ling Song

  DOI：10.1016/j.tetasy.2016.11.011

  日期：2017.1

  In this investigation, chiral thiophosphoramide 3d was easily prepared from chiral (1R,2R)-1,2-diphenylethylenediamine and then applied as an efficient chiral ligand in the catalytic asymmetric arylation reactions of various aromatic aldehydes. The corresponding diarylmethanol products were produced with good to excellent yields (up to 98%) and enantioselectivities (up to 94%). The recovery of chiral ligand 3d could be as high as 96%. (C) 2016 Elsevier Ltd. All rights reserved.