(S)-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: (S)-1-phenoxy-2-butanol
• 英文别名: (S)-1-phenoxybutan-2-ol；(2S)-1-phenoxybutan-2-ol
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ADCQEPDJMQFARS-VIFPVBQESA-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 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-1-phenoxy-2-butanol
  参考文献：
  名称：

  Ljubovic, Edina; Sunjic, Vitomir, Croatica Chemica Acta, 1998, vol. 71, # 1, p. 99 - 117

  摘要：

  DOI：

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。
• Enhanced selectivity in Novozym 435 catalyzed kinetic resolution of secondary alcohols and butanoates caused by the (R)-alcohols
  作者：Elisabeth Egholm Jacobsen、Erik van Hellemond、Anders Riise Moen、Lucia Camino Vazquez Prado、Thorleif Anthonsen

  DOI：10.1016/j.tetlet.2003.09.105

  日期：2003.11.10

  In esterifications of secondary alcohols catalyzed by immobilized lipase B from Candida antarctica (Novozym 435) the E-values decreased during the reaction. Hydrolysis of the corresponding butanoates showed the opposite effect. When an enantiopure (R)-alcohol, related but different, was added to the transesterification reaction, the E-value was significantly enhanced.

  在固定化来自南极假丝酵母的脂肪酶B （Novozym 435）催化的仲醇的酯化反应中，E值降低。相应的丁酸酯的水解显示相反的作用。当将相关但不同的对映体（R）-醇加入酯交换反应中时，E-值显着提高。
• Enantioselective Parallel Synthesis Using Polymer-Supported Chiral Co(salen) Complexes
  作者：Stefan Peukert、Eric N. Jacobsen

  DOI：10.1021/ol990920q

  日期：1999.10.1

  [GRAPHICS]The kinetic resolution of epoxides with phenols catalyzed by a polymer supported Co(salen) complex is applied to the first enantioselective catalytic synthesis of parallel libraries, The corresponding 1-aryloxy-2-alcohols are obtained in high yield, purity, and enantiomeric excess. Further elaboration with diversity elements provides highly efficient access to important classes of pharmacologically active compounds.
• 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.