(R)-1-phenoxy-2-butanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1-phenoxy-2-butanol
• 英文别名: (2R)-1-phenoxybutan-2-ol
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ADCQEPDJMQFARS-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-苯氧基-2-丁酮 在 sodium tetrahydroborate 、 乙酸乙烯酯 、 pseudomonas fluorescens lipase 作用下， 以 甲醇 、 正己烷 为溶剂， 生成 (R)-1-phenoxy-2-butanol
  参考文献：
  名称：

  Correlation between distance of the perturbing groups and enantioselectivity of the lipase catalyzed acetylation of acyclic sec alcohols

  摘要：

  Study of kinetic resolutions of racemic sec alcohols 1-4, by acetylation to 5-8 with a series of microbial lipases in n-hexane, revealed the broadest selectivity of Geotrichum candidum (GCL) and Candida cylindracea (CCL(S), from Sigma) lipase in accepting these conformationaly flexible substrates. Surprisingly, for both lipases non-monotonous correlation between E-value and the distance (n) of perturbing groups in 1-4 is observed. GCL preferred small and large substrates, whereas CCL preferred medium-size substrates. For GCL lipase a remarkable turnover of enantioselectivity was observed on going from 1-3 to 4, revealing that relative steric requirements of the larger phenoxy group vs. smaller methyl group does not control the enantioselective bias in the latter. For Candida cylindracea (CCL(A), from Amano) lipase the conversion and E vary in a monotonous fashion from smaller to larger substrates. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00484-3

文献信息

• Continuous Enantioselective Kinetic Resolution of Terminal Epoxides Using Immobilized Chiral Cobalt-Salen Complexes
  作者：Andreas Kirschning、Wladimir Solodenko、Gerhard Jas、Ulrich Kunz

  DOI：10.1055/s-2007-965877

  日期：2007.2

  Jacobsen’s cobalt-salen complex was covalently immobilized on polymer carriers that are part of different technical setups (polymer powder, composite Raschig rings, PASSflow microreactors) and employed for the enantioselective ring opening of terminal epoxides with water and phenols. The polymer-supported catalysts showed good activity and stereoselectivity and could be used repeatedly after a simple reactivation protocol in both batch as well as continuous-flow modes.

  Jacobsen 的钴-沙伦复合物被共价固定在不同技术装置的聚合物载体上（聚合物粉末、复合拉希环、PASSflow 微反应器），并用于端基环氧化物与水和酚类的手性选择性开环反应。聚合物支持的催化剂表现出良好的活性和立体选择性，并且在批量和连续流动模式下，经过简单的再活化程序后可以重复使用。
• Immobilization does not influence the enantioselectivity of CAL-B catalyzed kinetic resolution of secondary alcohols
  作者：Elisabeth Egholm Jacobsen、Liv Siri Andresen、Thorleif Anthonsen

  DOI：10.1016/j.tetasy.2004.11.081

  日期：2005.2

  Decreasing enantioselectivity (E-value) by increasing conversion has been observed in transesterification reactions of secondary alcohols catalyzed by a pure protein formulation of lipase B from Candida antarctica (Novozym 525 F). Addition of a range of enantiopure alcohols caused a temporary increase in selectivity of the transesterification reaction of 3-chloro-1-phenoxy-2-propanol with vinyl butanoate. The corresponding immobilized lipase B, (Novozym 435) showed a similar relationship between the E-value and degree of conversion. (C) 2004 Elsevier Ltd. All rights reserved.
• Correlation between distance of the perturbing groups and enantioselectivity of the lipase catalyzed acetylation of acyclic sec alcohols
  作者：Edina Ljubović、Vitomir Šunjić

  DOI：10.1016/s0957-4166(96)00484-3

  日期：1997.1

  Study of kinetic resolutions of racemic sec alcohols 1-4, by acetylation to 5-8 with a series of microbial lipases in n-hexane, revealed the broadest selectivity of Geotrichum candidum (GCL) and Candida cylindracea (CCL(S), from Sigma) lipase in accepting these conformationaly flexible substrates. Surprisingly, for both lipases non-monotonous correlation between E-value and the distance (n) of perturbing groups in 1-4 is observed. GCL preferred small and large substrates, whereas CCL preferred medium-size substrates. For GCL lipase a remarkable turnover of enantioselectivity was observed on going from 1-3 to 4, revealing that relative steric requirements of the larger phenoxy group vs. smaller methyl group does not control the enantioselective bias in the latter. For Candida cylindracea (CCL(A), from Amano) lipase the conversion and E vary in a monotonous fashion from smaller to larger substrates. (C) 1997, Elsevier Science Ltd.