(R)-1-phenylpropyl butyrate | 10031-86-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (R)-1-phenylpropyl butyrate
• 英文别名: (+)(R)-1-butyryloxy-1-phenyl-propane；(+)(R)-1-Butyryloxy-1-phenyl-propan；[(1R)-1-phenylpropyl] butanoate
• CAS: 10031-86-4；140390-61-0
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: SNUDRKNHOSAKGS-GFCCVEGCSA-N

物化性质

• 沸点：
  267.4±9.0 °C(Predicted)
• 密度：
  0.986±0.06 g/cm3(Predicted)
• LogP：
  3.87

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

制备方法与用途

毒性：GRAS (FEMA)。

使用限量：根据FDA §172.515 (2001)，各食品类别中的限量如下： - 饮料：0.13～1.0 mg/kg - 焙烤制品：0.14 mg/kg - 糖果：1.0 mg/kg - 冷饮：0.12～0.20 mg/kg

适量为限。

反应信息

• 作为产物：
  描述：

  正丁酸乙烯酯 、 1-苯丙醇 以 甲苯 为溶剂， 反应 20.0h， 以40%的产率得到(R)-1-phenylpropyl butyrate
  参考文献：
  名称：

  Biocatalysis in Organic Synthesis. 9. Highly Enantioselective Kinetic Resolution of Secondary Alcohols Catalyzed by Acylase.¹

  摘要：

  发现了来自阿斯pergillus物种的酶酰化酶 I (AA-I) 的一种新催化活性。尽管该酶之前仅用于水解 N-酰基氨基酸，但我们发现它是使用乙烯基酯作为酰基供体进行转酯化反应的高效催化剂。该方法已应用于多种次级醇的动力学分辨。

  DOI：

  10.1055/s-1997-796

文献信息

• Removal of the acyl donor residue allows the use of simple alkyl esters as acyl donors for the dynamic kinetic resolution of secondary alcohols
  作者：Gerard K.M. Verzijl、Johannes G. de Vries、Quirinus B. Broxterman

  DOI：10.1016/j.tetasy.2005.02.028

  日期：2005.5

  dynamic kinetic resolution of secondary alcohols using a lipase and a ruthenium catalyst as developed by Bäckvall required some improvements to make it suitable for its use in an industrial process. The use of p-chlorophenyl acetate as acyl donor is not desirable in view of the toxicity of the side product. We herein report that simple alkyl esters can be used as acyl donors if the alcohol or ketone residue

  Bäckvall开发的使用脂肪酶和钌催化剂的仲醇动态动力学拆分方法需要进行一些改进，以使其适合工业过程使用。p的使用考虑到副产物的毒性，不希望使用乙酸-氯苯酯作为酰基供体。我们在本文中报道，如果在反应过程中连续除去在酶促酰化过程中形成的醇或酮残基，则可以将简单的烷基酯用作酰基供体。酮的添加加快了外消旋过程，使我们减少了酶和钌催化剂的用量。探索了该方法的范围，并找到了合适范围的酰基供体。使用丁酸异丙酯或苯乙酸甲酯作为酰基供体，使各种苄醇和脂肪醇反应，在大多数情况下，酯的收率> 95％，ee分离为99％。此外，
• Shell Cross‐Linked Micelles as Nanoreactors for Enantioselective Three‐Step Tandem Catalysis
  作者：Michael Kuepfert、Aaron E. Cohen、Olivia Cullen、Marcus Weck

  DOI：10.1002/chem.201804956

  日期：2018.12.12

  enantio‐enriched alcohols in the cross‐linked shell, and nucleophilic base‐catalyzed acylation in the hydrophobic core. The catalysts are positioned in close proximity on a single micelle support to take advantage of the intramicellar substrate diffusion, yet they are sufficiently spaced apart from each other in physically distinct microenvironments. These compartmentalized micelles are substrate selective

  描述了组装成壳交联胶束（SCM）的功能化两亲性聚（2-恶唑啉）基三嵌段共聚物。这些胶束可通过分隔将三种不相容的催化剂进行位点分离，从而在一锅中实现三步非正交串联工艺。尤其是，在亲水性电晕中酸催化的缩酮水解为前手性酮，然后在交联壳中进行Rh催化的不对称转移氢化为对映体富集的醇，并在疏水核中进行了亲核碱催化的酰化反应。将催化剂紧密地放置在单个胶束载体上，以利用胶束内底物扩散的优势，但它们在物理上不同的微环境中彼此充分隔开。
• 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