(S)-1-phenylpentyl acetate | 87190-42-9

• 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-phenylpentyl acetate
• 英文别名: (-)(S)-1-acetoxy-1-phenyl-pentane；(-)(S)-1-Acetoxy-1-phenyl-pentan；(R,S)-Acetic acid 1-phenyl-pentyl ester；[(1S)-1-phenylpentyl] acetate
• CAS: 87190-42-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: UNBGLXOZZKYZEN-ZDUSSCGKSA-N

物化性质

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

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：

  苯戊酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氧化碳 为溶剂， 20.0 ℃ 、7.0 MPa 条件下， 反应 139.0h， 生成 (S)-1-phenylpentyl acetate
  参考文献：
  名称：

  Expanding substrate scope of lipase-catalyzed transesterification by the utilization of liquid carbon dioxide

  摘要：

  Secondary alcohols having bulky substituents on both sides of the chiral center are often poor substrates for most lipases. Here we reported that substrate scopes of two of the most used lipases, Candida antarctica lipase B and Burkholderia cepacia lipase, were found to be expanded toward more bulky secondary alcohols such as 1-phenyl-1-dodecanol and 2-methyl-1-phenyl-1-propanol by simply using them in liquid carbon dioxide as a solvent. The effects of solvents, reaction pressure, and pre-treatment of the enzyme with liquid CO2 on this acceleration phenomenon were also studied. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.11.052

文献信息

• Highly Focused Library‐Based Engineering of <i>Candida antarctica</i> Lipase B with ( <i>S</i> )‐Selectivity Towards <i>sec</i> ‐Alcohols
  作者：Yixin Cen、Danyang Li、Jian Xu、Qiongsi Wu、Qi Wu、Xianfu Lin

  DOI：10.1002/adsc.201800711

  日期：2019.1.11

  reversed (S)‐selectivity towards a series of sec‐alcohol with E values up to 115 (conv. 50%, ee 94%). Compared with the previously reported (S)‐selective CALB variant, W104A, a single mutation provided less selectivity, while the synergistic effects of three mutations in the best variant endow better (S)‐selectivity and a broader substrate scope than the W104A variant. Structural analysis and molecular

  南极假丝酵母脂肪酶B（CALB）是学术界和工业界使用最广泛的生物催化剂之一，对各种手性仲醇表现出显着的（R）-对映选择性。考虑到量身定制的立体选择性在有机合成中的重要性，发现具有高（R）和（S的对映体互补脂肪酶突变体）选择性是有价值的并且是非常需要的。在本文中，我们报告了一种高效的定向进化策略，在每个突变位点仅使用4个代表性氨基酸，即丙氨酸（A），亮氨酸（L），赖氨酸（K），色氨酸（W），创建了一个非常小的CALB变体需要更少的筛选。获得的具有三个突变W104V / A281L / A282K的最佳突变体显示出对一系列秒酒精的高度反向（S）选择性，E值高达115（转化率50％，ee 94％）。与先前报道的（S）选择性CALB变体W104A相比，单个突变提供的选择性较低，而最佳变体中的三个突变的协同作用赋予了更好的效果（S）选择性和比W104A型号更大的基材范围。结构分析和分子动力学模拟揭示了反向对映选择性的来源。
• Mutant Lipase-Catalyzed Kinetic Resolution of Bulky Phenyl Alkyl<i>sec</i>-Alcohols: A Thermodynamic Analysis of Enantioselectivity
  作者：Michaela Vallin、Per-Olof Syrén、Karl Hult

  DOI：10.1002/cbic.200900635

  日期：2010.2.15

  Open to persuasion: The rationally designed, single point mutated variant, Candida antarctica lipase B W104A, is a S‐selective catalyst for kinetic resolution of bulky phenyl alkyl alcohols. The catalyst's enantioselectivity differs within a homologous series of alcohols, depending on the different contributions from enthalpy and entropy.

  开放的说服力：合理设计的单点突变变体南极假丝酵母脂肪酶B W104A是一种S选择性催化剂，用于动力学分离大体积的苯基烷基醇。在同系列的醇中，催化剂的对映选择性不同，这取决于焓和熵的不同贡献。
• Mutated variant of Candida antarcticalipase B in (S)-selective dynamic kinetic resolution of secondary alcohols
  作者：Karin Engström、Michaela Vallin、Per-Olof Syrén、Karl Hult、Jan-E. Bäckvall

  DOI：10.1039/c0ob00748j

  日期：——

  An (S)-selective dynamic kinetic resolution of secondary alcohols, employing a mutated variant of Candida antarcticalipase B (CalB) gave products in 84–88% yield and in 90–97% ee.

  通过使用南极假丝酵母脂肪酶B（CalB）的突变变体，对仲醇进行（S）选择性动态动力学拆分，得到的产品收率为84-88％，ee为90-97％。
• LipG9-mediated enzymatic kinetic resolution of racemates: Expanding the substrate-scope for a metagenomic lipase
  作者：Juliana Christina Thomas、Robson Carlos Alnoch、Allen Carolina dos Santos Costa、Pamela Taisline Bandeira、Martha Daniela Burich、Suelem Kluconski Campos、Alfredo Ricardo Marques de Oliveira、Emanuel Maltempi de Souza、Fabio de Oliveira Pedrosa、Nadia Krieger、Leandro Piovan

  DOI：10.1016/j.mcat.2019.110402

  日期：2019.8

  from 4 to 63). In an opposite way, Im-LipG9 did not present activity for tertiary alcohols, amines and lactones. When compared to commercial lipases, Im-LipG9 enantioselectivity was superior to Candida rugosa lipase and equivalent to Candida antarctica lipase B. Thus, the chemo and enantioselectivity of LipG9 in EKR reactions were identified and its potential for asymmetric synthetic approaches was

  酶是生物系统的主要生物催化剂，如今它们在不对称有机合成中起着重要作用。微生物是酶的主要来源，但是，只有极小部分的微生物可以在实验室条件下进行培养，并且作为替代方案，宏基因组学方法允许从所谓的“不可培养的”微生物中获取新的酶。文献中已经描述了几类宏基因组酶。然而，关于其潜在的不对称生物转化的研究尚未得到充分利用。因此，我们介绍了我们最近在建立手性物质的酶促动力学拆分（EKR）中LipG9（宏基因组脂肪酶）的底物范围方面的工作。LipG9先前已被分离，固定并成功应用于脂肪醇的EKR中。在这项研究中，用LipG9分析了一系列可拆分的手性物质，仲苄醇/酯优先以比脂族醇描述的对映体选择性（E> 200）更好的对映选择性（E> 200）进行分离。相反，Im-LipG9对叔醇，胺和内酯没有活性。与商业脂肪酶相比，Im-LipG9对映选择性优于皱纹假丝酵母脂肪酶与南极假丝酵母脂肪酶B等效。因此，鉴定了Li
• Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine
  作者：Tadashi Ema、Norichika Ura、Masataka Yoshii、Toshinobu Korenaga、Takashi Sakai

  DOI：10.1016/j.tet.2009.09.058

  日期：2009.11

  We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure. and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products Could be predicted correctly in most cases (28 out of 30) (C) 2009 Elsevier Ltd All rights reserved