(1S)-1-(4-benzyloxyphenyl)ethan-1-ol | 119776-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S)-1-(4-benzyloxyphenyl)ethan-1-ol
• 英文别名: (S)-1-(4-(benzyloxy)phenyl)ethanol；(1S)-1-[4-(benzyloxy)phenyl]ethanol；(1S)-1-(4-phenylmethoxyphenyl)ethanol
• CAS: 119776-17-9
• 化学式: C₁₅H₁₆O₂
• mdl: MFCD09863701
• 分子量: 228.291
• InChiKey: NWTDSFYWJCAKFF-LBPRGKRZSA-N

物化性质

• 熔点：
  66.1-66.5 °C
• 沸点：
  376.5±30.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(4-(benzyloxy)phenyl)-2-fluoroethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 (S)-1-(4-(benzyloxy)phenyl)ethyl butanoate 、 (1S)-1-(4-benzyloxyphenyl)ethan-1-ol
  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

文献信息

• DMSO-triggered enhancement of enantioselectivity in Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols
  作者：Amrit Goswami、Jonali Goswami

  DOI：10.1016/j.tetlet.2005.03.147

  日期：2005.6

  Dimethyl sulfoxide as cosolvent enhances the enantioselectivity of resolved products up to 100% in the Novozyme[435]-catalyzed transesterification of chiral 1-phenylethanols but not 1-phenyl-2-haloethanols in THF. The reaction does not proceed in lipophilic and water-miscible polar solvents.

  二甲基亚砜作为助溶剂，在Novozyme [435]催化的手性1-苯基乙醇（而非1-苯基-2-卤代乙醇）在THF中的酯交换反应中，可将拆分产物的对映选择性提高至100％。该反应不会在亲脂性和水混溶性极性溶剂中进行。
• One-pot lipase-catalyzed synthesis of enantiopure secondary alcohols from carbonyl compounds: a new protocol for lipase-mediated resolution
  作者：Ahmed Kamal、Mahendra Sandbhor、K.Venkata Ramana

  DOI：10.1016/s0957-4166(02)00170-2

  日期：2002.5

  Reduction of acetophenones with sodium borohydride in the presence of neutral alumina in hexane followed by enantioselective acylation catalyzed by Pseudomonas cepacia lipase has been achieved in one-pot. Further, immobilized lipase offered a high degree of selectivity with spontaneity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic synthesis of enantiopure 1-phenyl-2-haloethanols and their esters
  作者：Sina Maria Lystvet、Bård Helge Hoff、Thorleif Anthonsen、Elisabeth Egholm Jacobsen

  DOI：10.3109/10242422.2010.501406

  日期：2010.7

  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.