(S)-1-(4-bromophenyl)ethyl acetate | 137408-29-8

• 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-(4-bromophenyl)ethyl acetate
• 英文别名: [(1S)-1-(4-bromophenyl)ethyl] acetate
• CAS: 137408-29-8
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: LYEDQQCOJXUBOX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1-(4-bromophenyl)ethyl acetate 生成 (S)-1-(4-bromophenyl)ethyl acetate
  参考文献：
  名称：

  Synthesis of Chiral 1-Arylalkan-1-ols Using Crude Enzymes

  摘要：

  Enantioselective hydrolysis of racemic l-acetoxy-l-arylalkanes has been examined by two selected enzymes, crude pig liver acetone powder and crude goat liver acetone powder, providing l-arylalkan-l-ols in high optical purities.

  DOI：

  10.1080/00397919108021776

文献信息

• Synthesis of Chiral Aromatic Alcohols: Use of New C₂-Symmetric Rh^IIICp∗, Ru^II(cymene), or Ru^II(benzene) Complexes Containing Chiral Diaminocyclohexane Ligand as Asymmetric Transfer Hydrogenation Catalyst
  作者：Rubén Montalvo-González、Daniel Chávez、Gerardo Aguirre、Miguel Parra-Hake、Ratnasamy Somanathan

  DOI：10.1080/00397910802663451

  日期：2009.7.7

  Abstract Twelve chiral secondary alcohols were synthesized by asymmetric transfer hydrogenation (ATH) using C2-symmetric bis(sulfonamide) ligand (2) derived from (1R,2R)-cyclohexane-1,2-diamine and complexed with [RhCl2Cp*]2, [RuCl2(cymene)]2, or [RuCl2(benzene)]2 and then used in situ in the reduction of prochiral ketones. The alcohols were obtained in 85–99% yield and 90–99% enantioselectivity with

  摘要 使用衍生自 (1R,2R)-环己烷-1,2-二胺并与 [RhCl2Cp*]2 络合的 C2-对称双（磺酰胺）配体 (2)，通过不对称转移氢化 (ATH) 合成了 12 种手性仲醇， [RuCl2(cymene)]2 或 [RuCl2(苯)]2，然后原位用于还原前手性酮。以异丙醇作为氢源以 85-99% 的收率和 90-99% 的对映选择性获得醇。使用复合物 [RhCl2Cp*]2 和甲酸钠水溶液作为氢源，以 80-99% 的对映选择性实现了两倍的速率提高和更好的产率（88-99%）。
• Ionic liquids for enhancing the enantioselectivity of isolated BVMO-catalysed oxidations
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Marco W. Fraaije、Vicente Gotor

  DOI：10.1039/c0gc00560f

  日期：——

  The present study describes the first-time usage of an isolated thermostable Baeyer–Villiger monooxygenase (phenylacetone monooxygenase, PAMO) in the presence of ionic liquids. The stability, activity and selectivity of PAMO as an oxidative enzyme in the presence of different ionic liquids were studied. This revealed that the addition of some specific ionic liquids, such Ammoeng™ 102 and [bmim]MeSO4, can significantly enhance the E-value in the oxidation of racemic benzylketones. Moreover, the use of ionic liquids increases the optimal substrate concentration for performing Baeyer–Villiger oxidation, thereby extending the biocatalytic repertoire of PAMO for synthetic applications.

  本研究首次报道了在离子液体存在下使用分离的耐热贝耶尔-维利格单氧合酶（苯丙酮单氧合酶，PAMO）的情况。研究了不同离子液体存在下，PAMO作为氧化酶的稳定性、活性和选择性。结果显示，添加某些特定离子液体，如AmMOeng™ 102和[bmim]MeSO4，可以显著提高消旋苯甲酮氧化反应的E值。此外，离子液体的使用提高了进行贝耶尔-维利格氧化反应的最佳底物浓度，从而扩大了PAMO在合成应用中的生物催化范围。
• CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability
  作者：Xiu Xing、Jun-Qi Jia、Jing-Fan Zhang、Zi-Wen Zhou、Jun Li、Na Wang、Xiao-Qi Yu

  DOI：10.3390/molecules24030490

  日期：——

  immobilization of lipase and resolution of racemic 1-phenylethanol were investigated. Under optimal conditions, esters could be obtained with conversion of 50%, enantiomeric excess of product (eep) > 99%, enantiomeric excess of substrate (ees) > 99%, and enantiomeric ratio (E) > 1000. The magnetic CALB CLEAs were successfully used for enzymatic kinetic resolution of fifteen secondary alcohols. Compared with Novozym

  在这项研究中，开发并研究了南极假丝酵母脂肪酶B磁性交联酶聚集体的固定化策略。通过常规的共沉淀制备磁性颗粒。用3-氨基丙基三乙氧基硅烷（APTES）对磁性纳米粒子进行改性，以获得表面氨基官能化的磁性纳米粒子（APTES⁻Fe3 O 3）作为固定材料。戊二醛用作交联剂以使CALB与APTES⁻Fe₃O₃共价结合。研究了固定化脂肪酶和拆分外消旋1-苯基乙醇的最佳条件。在最佳条件下，可以以50％的转化率，产物的对映体过量（eep）> 99％，底物的对映体过量（ee）> 99％和对映体比率（E）> 1000获得酯。磁性CALB CLEAs已成功用于15种仲醇的酶动力学拆分。与Novozym 435相比，CALB CLEA磁性对大多数底物表现出更好的对映选择性。在48小时的反应周期中，将磁性CALB CLEA重复使用10次后，转化率仍大于49％。ee和eep都接近99％。此外，在-20℃下保存90天后，催化活性和对映选择性几乎没有降低。
• Kinetic resolution of secondary alcohols mediated by rabbit gastric lipase
  作者：Jean-Yves Legros、Martial Toffano、Sally K. Drayton、Michael Rivard、Jean-Claude Fiaud

  DOI：10.1016/s0040-4039(97)00242-6

  日期：1997.3

  Secondary benzylic alcohols were kinetically resolved by rabbit gastric lipase-mediated acylation with isopropenyl acetate. Among all the substrates tested, a high enantioselectivity was observed only for 1-[2-(6-methoxy)naphthyl]ethanol 3a (E>500). Allylic alcohols 14a and 15a were also efficiently resolved (E = 26 and 51 respectively).

  通过兔子胃脂肪酶介导的乙酸异丙烯酯基的酰化反应动力学拆分仲苄醇。在所有测试的底物中，仅对1- [2-（6-甲氧基）萘基]乙醇3a（E > 500）观察到高对映选择性。烯丙醇14a和15a也得到了有效拆分（分别为E = 26和51）。
• Enhancement of (stereo)selectivity in dynamic kinetic resolution using a core–shell nanozeolite@enzyme as a bi-functional catalyst
  作者：Wanlu Wang、Xiang Li、Zhoujun Wang、Yi Tang、Yahong Zhang

  DOI：10.1039/c4cc02112f

  日期：——

  A core-shell nanozeolite@enzyme bi-functional catalyst is constructed, which greatly improves selectivity and stereoselectivity of products in dynamic kinetic resolution of aromatic secondary alcohols compared with mixed catalysts, especially those involving small acyl donors.

  构造了一种核-壳型纳米沸石@酶双功能催化剂，与混合催化剂相比，特别是涉及小酰基给体的那些催化剂，可大大提高芳族仲醇动态动力学拆分中产物的选择性和立体选择性。