(S)-1-phenyl-1-propyl butyrate | 264885-61-2

• 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: (S)-1-phenyl-1-propyl butyrate
• 英文别名: (S)-1-phenylpropyl butyrate；[(1S)-1-phenylpropyl] butanoate
• CAS: 264885-61-2
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: SNUDRKNHOSAKGS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正丁酸2,2,2-三氟乙酯 、 1-苯丙醇 在 C₄₃H₃₅ClO₉Ru 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以86%的产率得到(S)-1-phenyl-1-propyl butyrate
  参考文献：
  名称：

  离子表面活性剂包衣的枯草杆菌蛋白酶：活性，对映体选择性，及其在仲醇的动态动力学拆分中的应用

  摘要：

  在这项工作中，我们探索了涂覆离子表面活性剂的地衣芽孢杆菌枯草杆菌蛋白酶（ISCBLS）作为仲醇动态动力学拆分催化剂的用途。通过将地衣芽孢杆菌枯草杆菌蛋白酶与离子表面活性剂1和糊精一起冻干来制备ISCBLS 。ISCBCL在N的酯交换反应中显示出比其天然对应物高9300倍的活性-乙酰基苯丙氨酸乙酯与1-丙醇在己烷中的反应，在丁酸三氟乙基酯与1-苯乙醇在THF中的酯交换反应中具有12800倍的增强活性。在丁酸三氟乙酯存在下，以50种仲醇为动力学拆分底物，对ISCBLS的对映选择性进行了研究。ISCBLS对大多数测试的仲醇显示出合成有用的对映选择性。ISCBLS的对映选择率为特别是良好的高为米-或p -取代1-苯基乙醇。通过ISCBLS和钌基外消旋催化剂的组合，这些仲醇的DKR提供了（S）-配置，效果良好（80-94％的收率，90-99％的ee）。结论是，ISCBLS作为（R）-选择性脂肪酶的对

  DOI：

  10.1039/c7ob02181j

文献信息

• Improved Enantioselectivity of Subtilisin Carlsberg towards Secondary Alcohols by Protein Engineering
  作者：Robin Dorau、Tamás Görbe、Maria Svedendahl Humble

  DOI：10.1002/cbic.201700408

  日期：2018.2.16

  An acyl in the hole: The performance of the serine protease subtilisin Carlsberg (SC) is improved towards transacylation reactions by using secondary alcohols in THF. By enzyme immobilization, the enantioselectivity of SC is increased tenfold. By further protein engineering, an enzyme variant (G165L/M221F) shows increased conversion, enantioselectivity (E>100), substrate scope, and stability in THF

  孔中的酰基：通过在THF中使用仲醇，丝氨酸蛋白酶枯草杆菌蛋白酶Carlsberg（SC）的性能可提高转酰基反应的效率。通过酶固定，SC的对映选择性增加了十倍。通过进一步的蛋白质工程，酶变体（G165L / M221F）显示出增加的转化率，对映选择性（E > 100），底物范围和在THF中的稳定性。
• Combinatorial Library Based Engineering of<i>Candida antarctica</i>Lipase A for Enantioselective Transacylation of<i>sec</i>-Alcohols in Organic Solvent
  作者：Ylva Wikmark、Maria Svedendahl Humble、Jan-E. Bäckvall

  DOI：10.1002/anie.201410675

  日期：2015.3.27

  A method for determining lipase enantioselectivity in the transacylation of sec‐alcohols in organic solvent was developed. The method was applied to a model library of Candida antarctica lipase A (CalA) variants for improved enantioselectivity (E values) in the kinetic resolution of 1‐phenylethanol in isooctane. A focused combinatorial gene library simultaneously targeting seven positions in the enzyme

  开发了一种测定有机溶剂中仲醇转酰基反应中脂肪酶对映选择性的方法。该方法应用于南极假丝酵母脂肪酶 A (CalA) 变体模型库，以提高 异辛烷中 1-苯基乙醇的动力学拆分的对映选择性（ E值）。设计了同时靶向酶活性位点七个位置的集中组合基因库。通过组氨酸标签（His 6标签）将酶变体固定在镍包被的 96 孔微量滴定板上，筛选异辛烷中 1-苯基乙醇的转酰基作用，并通过 GC 进行分析。双突变体 Y93L/L367I 显示出最高的对映选择性。该酶变体的E 值为 100 ( R )，比野生型 CalA ( E = 3) 有了显着改进。该变体还对测试的其他仲醇表现出高至优异的对映选择性。
• Enzyme reactions in apolar solvent. 5. The effect of adjacent unsaturation on the porcine pancreatic lipase catalyzed kinetic resolution of secondary alcohols
  作者：Brian Morgan、Allan C. Oehlschlager、Thomas M. Stokes

  DOI：10.1021/jo00037a049

  日期：1992.5

  The effect of adjacent unsaturation on the enzyme-catalyzed kinetic resolution of secondary alcohols is studied for a series of allylic, homoallylic, propargylic, homopropargylic, and phenyl-substituted 2-alkanols, using porcine pancreatic lipase (PPL) in anhydrous Et2O. Excellent enantioselectivity (high E value) was observed for alpha-phenethyl alcohol (3), propargylic alcohols (8 and 11), and (E)-allylic alcohols (9 and 12), but (Z)-allylic alcohols (10 and 13) showed poor selectivity. Enantioselectivity was also low for both (E)- and (Z)-homoallylic alcohols (15 and 16), homopropargylic alcohol (14), I-phenyl-2-propanol (6), and 4-phenyl-2-butanol (7). The enhanced enantioselectivity observed for (E)-allylic alcohols was exploited in the synthesis of the enantiomers of both components of the aggregation pheromone of the lesser grain borer, Rhyzopertha dominica (F.). The magnitude of the enantiomeric ratio (E value) can be dramatically affected by the accuracy of the values of ee(s) and ee(p) used in the calculation, especially when E is large. Variation in the value of E with the optical purity of the chiral derivatizing agent used to determine ee(s) and ee(p) is illustrated.
• AnS-Selective Lipase Was Created by Rational Redesign and the Enantioselectivity Increased with Temperature
  作者：Anders O. Magnusson、Mohamad Takwa、Anders Hamberg、Karl Hult

  DOI：10.1002/anie.200500971

  日期：2005.7.18
• Enantioselective transesterification catalysis by nanosized serine protease subtilisin Carlsberg particles in tetrahydrofuran
  作者：Betzaida Castillo、Yamixa Delgado、Gabriel Barletta、Kai Griebenow

  DOI：10.1016/j.tet.2010.01.053

  日期：2010.3

  Enzyme catalysis in organic solvents is a powerful tool for stereo-selective synthesis but the enantioselectivity is still hard to pi edict To overcome this obstacle. we employed a nanoparticulate formulation of subtilisin Carlsberg (SC) and designed a series of 14 structurally related racemic alcohols They were employed in the model transesterification reaction with vinyl butyrate and the enantioselectivities were determined. In general. short alcohol side chains led to low enantioselectivties, while larger and bulky side chains caused better discrimination of the enantiomers by the enzyme With several bulky substrates high enantioselectivities with E>100 were obtained Computational modeling highlighted that key to high enantioselectivity is the discrimination of the R and S substrates by the sole hydrophobic binding pocket based on their size and bulkiness While bulky S enantiomer side chains could be accommodated within the binding pocket, bulky R enantiomer side chains could not However, when also the S enantiomer side chain becomes too large and does not fit into the binding pocket anymore. enantioselectivity accordingly drops (C) 2010 Elsevier Ltd All rights reserved