(+/-)-1-(4-benzyloxyphenyl)-2-fluoroethanol | 1073056-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-1-(4-benzyloxyphenyl)-2-fluoroethanol
• 英文别名: 1-(4-(benzyloxy)phenyl)-2-fluoroethanol
• CAS: 1073056-20-8
• 化学式: C₁₅H₁₅FO₂
• 分子量: 246.281
• InChiKey: MXIWICAXFVFKIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 (+/-)-1-(4-benzyloxyphenyl)-2-fluoroethanol 在 immobilized Novozym 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 168.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters

  摘要：

  Several secondary haloalcohols have been resolved by esterification catalyzed by lipases A and B from Candida antarctica (CALA and CALB, respectively). Immobilized CALB (Novozym 435) gave better selectivities and faster reaction rates than CALA (Novozyme 735) with all of the substrates. Vinyl butanoate was the favoured acyl donor compared to vinyl acetate due to remarkably faster reactions. The alcohols (R)-2a, (R)-2c and the butanoates (S)-3a-c have been isolated with 98-99% enantiomeric excess (ee) in good yields.

  DOI：

  10.3109/10242422.2010.501406
• 作为产物：
  描述：

  1-(4-(benzyloxy)phenyl)-2-fluoroethanone 在 sodium tetrahydroborate 作用下， 生成 (+/-)-1-(4-benzyloxyphenyl)-2-fluoroethanol
  参考文献：
  名称：

  Asymmetric reduction using (R)-MeCBS and determination of absolute configuration of para-substituted 2-fluoroarylethanols

  摘要：

  The asymmetric reduction of eight alpha-fluoroacetophenones has been investigated using (R)-MeCBS as a catalyst in various media. Based on a solvent screen, 1,2-dimethoxyethane, diethyl ether and dichloromethane were used in reductions of the alpha-fluoroacetophenones. The enantiomeric excess of the products depended oil the solvent and the electronic character of the aromatic substituents. Higher enantioselectivity and less solvent dependency were observed in the reduction of substrates bearing electron donating substituents, whereas the opposite was the case for reduction of the substrates with electron withdrawing substituents. The (R)-2-fluoro-1-arylethanols were obtained with enantiomeric excesses in the range of 91-99% using 1,2-dimethoxyethane as a solvent. Six of the alcohols produced are new chemical entities. The absolute configurations of the (R)-2-fluoro-1-arylethanols were determined by circular dichroism using the exciton chirality method of tile (S)-benzoate esters of the alcohols. The (S)-benzoate esters were obtained by lipase-catalysed resolution using Novozym 435. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.019