(R)-1-phenylethyl hexanoate

• 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-phenylethyl hexanoate
• 英文别名: [(1R)-1-phenylethyl] hexanoate
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XDNXTDFSRYCZFT-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  己酸 在 N-甲基吗啉 、 Novozym SP₄₃₅ 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.5h， 生成 (R)-1-phenylethyl hexanoate
  参考文献：
  名称：

  脂肪酶催化混合羧酸碳酸酐的手性酸或醇的拆分

  摘要：

  混合羧酸碳酸酐是有机介质中脂肪酶催化酯化反应的有效不可逆酰基转移试剂，可用于拆分手性羧酸或醇类。

  DOI：

  10.1016/0040-4020(96)00083-x

文献信息

• New air-stable iron catalyst for efficient dynamic kinetic resolution of secondary benzylic and aliphatic alcohols
  作者：Qiong Yang、Na Zhang、Mingke Liu、Shaolin Zhou

  DOI：10.1016/j.tetlet.2017.05.038

  日期：2017.6

  catalyst system for the dynamic kinetic resolution of secondary alcohols by combining the enzymatic resolution with an iron-catalyzed racemization. A new air-stable tricarbonyl (cyclopentadienone)iron complex is identified as the active racemization catalyst for this transformation without any additive. Various substrates including benzylic, heteroaromatic, aliphatic alcohols can be used and afford the

  我们在此报道了通过将酶促拆分与铁催化的外消旋相结合来实现仲醇的动态动力学拆分的催化剂体系。一种新型的空气稳定的三羰基（环戊二烯酮）铁络合物被确定为该外消旋的活性外消旋催化剂，无任何添加剂。可以使用各种底物，包括苄基，杂芳族，脂族醇，并以良好的收率和优异的对映选择性提供相应的酯。
• 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％。
• Easy and Simple SiO2 Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases
  作者：Mateus Mittersteiner、Tayani Machado、Paulo Cesar de Jesus、Patrícia Brondani、Dilamara Scharf、Renato Wendhausen Jr.

  DOI：10.21577/0103-5053.20160277

  日期：——

  In this study, lipase from Candida antarctica B (Lipozyme CaLB-L) was successfully immobilized on SiO2 through adsorption and used to obtain (R)-(+)-esters derived from (R, S)-1-phenylethanol. The new immobilized enzyme was compared with commercially immobilized lipases (Novozyme 435, Lipozyme 435 and Pseudomonas cepacia (PSC-II and PSD-I)). Lipozyme CaLB-L adsorbed onto SiO2 was found to be a good catalyst and, under optimal conditions, esters could be obtained with conversion 44%, enantiomeric excess of product (ee(p)) > 99%, enantiomeric excess of substract (ee(s)) 77% and enantiomeric ratio (E) > 200. The lipase maintained enantioselectivity under adverse conditions, such as in organic solvents, with an excess of substrate and at different temperatures. The immobilized lipase could be reused five times with no significant loss of the activity.
• Highly enantioselective aminoacylase-catalyzed transesterification of secondary alcohols
  作者：M Bakker、A.S Spruijt、F van Rantwijk、R.A Sheldon

  DOI：10.1016/s0957-4166(00)00118-x

  日期：2000.5

  The aminoacylase (N-acyl-L-amino acid amidohydrolase; E.C. 3.5.1.14) from Aspergillus melleus, a readily available inexpensive enzyme, catalyzes the transesterification of a wide range of chiral secondary arylalkanols with essentially absolute stereoselectivity (E > 500). Moreover, the productivities obtained with 1-phenylethanol, 1-phenylpropanol, 1-(1-naphthyl)ethanol and 1-(2-naphthyl)ethanol were substantially higher than those in the corresponding lipase-catalyzed transesterifications. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Lipase catalyzed resolution of chiral acids or alcohols using mixed carboxylic-carbonic anhydrides
  作者：Eryka Guibé-Jampel、Zbigniew Chalecki、Mohamed Bassir、Mirjana Gelo-Pujic

  DOI：10.1016/0040-4020(96)00083-x

  日期：1996.3

  Mixed carboxylic-carbonic anhydrides are efficient irreversible acyl transfer reagents for lipase catalyzed esterification in organic media, and can be used for the resolution of chiral carboxylic acids or alcohols.

  混合羧酸碳酸酐是有机介质中脂肪酶催化酯化反应的有效不可逆酰基转移试剂，可用于拆分手性羧酸或醇类。