(S)-1-phenylethyl dodecanoate

• 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-phenylethyl dodecanoate
• 英文别名: 1-phenylethyl laurate；1‑phenylethyl dodecanoate；[(1S)-1-phenylethyl] dodecanoate
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: AOOSIBUUMZYKMN-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  月桂酰氯 在 吡啶 、 Candida cylindracea lipase 、 水 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 (S)-1-phenylethyl dodecanoate
  参考文献：
  名称：

  迁移基团结构对脂肪酶催化动力学拆分 1-苯基乙醇对映选择性的影响

  摘要：

  摘要 我们研究了酰基部分对三种脂肪酶的对映选择性的影响：南极念珠菌 B、洋葱假单胞菌和圆柱念珠菌，常用于通过酰化或水解进行动力学拆分。在 1-苯基乙醇的酯交换和相应苯乙基酯的水解过程中，使用各种烯醇酯检测酰基的大小。C. antarctica-B 脂肪酶在 1-苯基乙醇与异丙烯基和乙酸乙烯酯、癸酸乙烯酯、月桂酸乙烯酯的酯交换中显示出最高的选择性（E > 200）。1-苯基-乙基-乙酸酯、癸酸酯和月桂酸酯也可以用 CAL-B 以高选择性 (E > 150) 水解。结果可以与每种脂肪酶的三维形式相关联。

  DOI：

  10.1016/j.crci.2016.05.002

文献信息

• Two Approaches for CAL-B-Catalyzed Enantioselective Deacylation of a Set of α-Phenyl Ethyl Esters: Organic Solvent with Sodium Carbonate and Micro-aqueous Medium
  作者：Samra Razi、Saoussen Zeror、Mounia Merabet-Khelassi、Emilie Kolodziej、Martial Toffano、Louisa Aribi-Zouioueche

  DOI：10.1007/s10562-020-03525-0

  日期：2021.9

  buffer solution pH 7 in the second. The results show the high efficiency of the deacylation in the presence of the sodium carbonate for the enzymatic resolution of all the esters and that in term of reactivity (31% ≤ conv ≤ 50%) and selectivity (E > 200). While, during the hydrolysis in micro-aqueous media, the conversion is strongly affected by the length of the acyl-chain side, the conversion decreases

  在此，我们报告了通过比较两种反应方法：无水介质和碳酸钠，由来自南极念珠菌 (CAL-B) 的脂肪酶 B 催化的一组不同链长的 α-苯基乙酯的酰基部分的有效对映选择性裂解和微水介质。脱酰反应在有机溶剂中进行，第一种情况是在 Na2CO3 存在下，第二种情况是加入一滴 pH 为 7 的磷酸盐缓冲溶液。结果表明，在碳酸钠存在下，酶解所有酯的脱酰效率高，反应性 (31% ≤ conv ≤ 50%) 和选择性 (E > 200)。而在微水介质中水解时，转化率受酰基链侧长度的影响很大，转化率从 1-苯基乙酸乙酯 1a 的 conv = 50% 降低到 1-十二烷酸 1-苯基乙酯 6a 的 conv = 19%，即使选择性仍然很高（E > 89）。在这两种条件下，脂肪酶 CAL-B 都显示出高对映选择性，有利于 (R)-1-苯基乙醇对映异构体（转换率 > 45%，E > 200），但反应性受酰基的形式和大小调节。链侧。
• Low-temperature enzymatic hydrolysis resolution in mini-emulsion media
  作者：Nuno M. T. Lourenço、Sara C. Matias、Margarida C. Altas、Luis P. Fonseca

  DOI：10.1515/chempap-2015-0032

  日期：2015.1.1

  mini-emulsion size was observed. For the longer 1-phenylethyl ester, 1-phenylethyl dodecanoate, the enzymatic resolution was promoted exclusively at low temperatures. The preparative mini-emulsion enzymatic reaction of 1-phenylethyl dodecanoate at 4 °C afforded the isolation of (R)-phenylethanol with a yield of 36 % with an ee of 99 %. (S)-Phenylethanol was isolated with a 51 % yield with an ee of 79 %.

  首次描述了一种用于酶解1-苯基乙醇的低温微乳液介质。在小乳液介质中，在南极假丝酵母脂肪酶B存在下，具有不同链长的1-苯基乙基酯的酶促水解拆分显示受温度显着控制。在该系统中，观察到温度对微乳液尺寸的直接影响。对于更长的1-苯基乙基酯，即十二烷基1-苯基乙基酯，仅在低温下才提高了酶促分离度。1-苯基乙基十二烷酸酯在4°C的制备型微乳液酶促反应可分离出（R）-苯基乙醇，收率为36％，ee为99％。（S分离出苯基乙醇，产率为51％，ee为79％。
• Fatty and aromatic acids as acyl donors in enzymatic kinetic resolution of phenylethanol and 1-phenylpropan-2-ol
  作者：Fatma Zohra Smaine、Mounia Merabet-Khelassi、Saoussen Zeror、Emilie Kolodziej、Martial Toffano、Louisa Aribi-Zouioueche

  DOI：10.1007/s00706-023-03147-3

  日期：2024.1

  The use of fatty and aromatic acids as green acyl donors for enzymatic kinetic resolution via esterification of 1-phenylethanol and 1-phenylpropan-2-ol was described. The impact of the presence of magnesium sulfate on both reactivity and selectivity of Candida rugosa lipase (CRL) was checked. The organic solvents, the medium dilution, and the temperature revealed as determinant parameters to achieve

  描述了使用脂肪酸和芳香酸作为绿色酰基供体，通过 1-苯基乙醇和 1-苯基丙-2-醇的酯化进行酶动力学拆分。检查了硫酸镁的存在对假丝酵母脂肪酶 (CRL)的反应性和选择性的影响。有机溶剂、介质稀释度和温度是实现对映选择性酯化反应的决定性参数。在使用丁酸和月桂酸作为酰基供体拆分 1-苯基乙醇过程中，硫酸镁的使用对庚烷中 CRL 的对映选择性产生了显着影响。 图形概要
• A Lipid-Coated Lipase as an Enantioselective Ester Synthesis Catalyst in Homogeneous Organic Solvents
  作者：Yoshio Okahata、Yoshitaka Fujimoto、Kuniharu Ijiro

  DOI：10.1021/jo00112a052

  日期：1995.4

  A lipid-coated lipase was prepared, in which hydrophilic head groups of lipids interact with the hydrophilic surface of the enzyme and lipophilic alkyl chains extend away from its surface and solubilize the enzyme in hydrophobic organic solvents. Enantioselective esterification of(R)- or (S)-1-phenylethanol with aliphatic acid was studied in the presence of the lipid-coated lipase, solubilized homogeneously in organic solvents, by varying lipase origin, coating lipid molecules, reaction media, and substrate structures. The lipid-coated lipase prepared from the glycolipid (1) and lipase B from Pseudomonas fragi 22-39B showed both a high catalytic activity and enantioselectivity for the esterification of (R)-1-phenylethanol with long-chain aliphatic acid in dry isooctane, relative to other enzyme systems such as poly(ethylene glycol)-grafted lipase, lipase powder directly dispersed in organic solvents, and a water/organic emulsion system. The coating lipids are found to not affect the enzyme reactions and to act simply as lipophilic tails in organic media. The lipid-coated lipase is suitable for studying the reaction mechanism of the enzyme in organic solvents since the reaction is carried out in homogeneous media. It has been found in studying Michaelis-Menten kinetics that the lipid-coated lipase (or native lipase) has two binding sites for long-chain aliphatic acids and for enantiomorphic secondary alcohols having a small methyl and a large phenyl side chain. Aliphatic acid is bound first and then alcohol. The enantioselectivity of the esterification is determined by the nucleophilic attack of the enantiomorphic alcohol, but not in the binding process of the enantiomorphic alcohol.
• The effect of the migrating group structure on enantioselectivity in lipase-catalyzed kinetic resolution of 1-phenylethanol
  作者：Nedjma Melais、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.crci.2016.05.002

  日期：2016.8

  Abstract We have studied the effects of the acyl moiety on the enantioselectivity of three lipases: Candida antarctica B, Pseudomonas cepacia and Candida cylindracea, frequently used in kinetic resolutions by acylation or hydrolysis. The size of the acyl group was examined using various enol esters during the transesterification of 1-phenylethanol and the hydrolysis of the corresponding phenylethylesters

  摘要 我们研究了酰基部分对三种脂肪酶的对映选择性的影响：南极念珠菌 B、洋葱假单胞菌和圆柱念珠菌，常用于通过酰化或水解进行动力学拆分。在 1-苯基乙醇的酯交换和相应苯乙基酯的水解过程中，使用各种烯醇酯检测酰基的大小。C. antarctica-B 脂肪酶在 1-苯基乙醇与异丙烯基和乙酸乙烯酯、癸酸乙烯酯、月桂酸乙烯酯的酯交换中显示出最高的选择性（E > 200）。1-苯基-乙基-乙酸酯、癸酸酯和月桂酸酯也可以用 CAL-B 以高选择性 (E > 150) 水解。结果可以与每种脂肪酶的三维形式相关联。