1-(3-chlorophenyl)ethyl acetate | 19759-26-3

• 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: 1-(3-chlorophenyl)ethyl acetate
• CAS: 19759-26-3
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: MHPGGMAHRYXWQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(3-chlorophenyl)ethyl acetate 在 甲醇 、 potassium permanganate 作用下， 以99%的产率得到1-(3-氯苯基)乙醇
  参考文献：
  名称：

  一锅中KMnO4催化的乙酸化学选择性脱保护和可控的脱乙酰化-氧化

  摘要：

  利用催化的KMnO 4，开发了一种在环境条件下进行化学选择性脱乙酰反应的新型有效方案。KMnO 4的化学计量使用突显了一种异质氧化剂的双重作用，该异质氧化剂可在一锅顺序进行的脱乙酰基氧化反应中直接进入芳族醛。该反应采用另一种溶剂体系，并允许乙酸苄基酯在一个步骤中从干净转化为敏感的醛，同时防止过度氧化成酸。使用廉价且易于获得的KMnO 4作为环境友好的试剂以及反应操作的简便性特别吸引人，并且使得在先前步骤中乙酸盐的受控氧化和易裂解成为可能。

  DOI：

  10.1039/d0nj04321d
• 作为产物：
  描述：

  醋酸叔丁酯 、 1-(3-氯苯基)乙醇 在 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到1-(3-chlorophenyl)ethyl acetate
  参考文献：
  名称：

  碱催化的醇与未活化酯的选择性酯化

  摘要：

  已经开发了一种实用且有效的碱催化的酯化反应，用于从简单的醇与未活化的叔丁酯容易地合成多种酯。该方案可以在温和的条件下进行，以高至优异的产率提供酯，具有良好的功能耐受性。机理研究提供了叔丁基醇盐金属与醇交换的证据，产生了新的醇盐参与酯交换反应。

  DOI：

  10.1039/c8ob02411a

文献信息

• Superacid BF₃–H₂O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
  作者：Shuting Zhang、Xiaohui Zhang、Xuege Ling、Chao He、Ruofeng Huang、Jing Pan、Jiaqiang Li、Yan Xiong

  DOI：10.1039/c4ra04059g

  日期：——

  An efficient in situ prepared superacid BF₃–H₂O promoted benzylation of arenes using benzyl alcohols and acetates achieves various diarylalkanes.

  一种高效的原位制备的超强酸BF3-H2O促进的芳烃苄基化反应，使用苄醇和醋酸酯制备各种二芳基烷烃。
• Separation of enantiopure m-substituted 1-phenylethanols in high space-time yield using Bacillus subtilis esterase
  作者：Gao-Wei Zheng、Xu-Yun Liu、Zhi-Jun Zhang、Ping Tian、Guo-Qiang Lin、Jian-He Xu

  DOI：10.1039/c3ra41999a

  日期：——

  A recombinant Bacillus subtilis esterase (BsE) expressed in E. coli was found to exhibit excellent enantioselectivity (E was always greater than 100) towards m-substituted 1-phenylethanol acetates in the enantioselective hydrolysis reaction. An explanation for the high enantioselectivity observed towards these substrates was provided by molecular modeling. Moreover, the BsE also showed strong tolerance towards a high concentration of m-substituted 1-phenylethanol acetates (up to 1 M). Based on these excellent catalytic properties of BsE, a kind of m-substituted 1-phenylethanols, (R)-1-(3-chlorophenyl)ethanol, was efficiently synthesized in space-time yield of 920 g per L per day and 97% ee, indicating that the BsE was considered as a potentially ideal and promising biocatalyst for large-scale production of optically active m-substituted 1-phenylethanols.

  研究发现，在大肠杆菌中表达的重组枯草芽孢杆菌酯酶（BsE）在对映选择性水解反应中对 m-取代的 1-苯基乙醇乙酸酯表现出极好的对映选择性（E 始终大于 100）。分子模型为观察到的对这些底物的高对映选择性提供了解释。此外，BsE 还对高浓度的间取代 1-苯基乙醇乙酸酯（高达 1 M）表现出很强的耐受性。基于 BsE 的这些优异催化特性，一种间代 1-苯基乙醇--(R)-1-(3-氯苯基)乙醇被高效合成，时空产率为 920 克/升/天，ee 为 97%，这表明 BsE 被认为是大规模生产具有光学活性的间代 1-苯基乙醇的一种潜在的理想和有前途的生物催化剂。
• Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols
  作者：Luciana L. Machado、Telma L.G. Lemos、Marcos Carlos de Mattos、Maria da Conceicão F. de Oliveira、Gonzalo de Gonzalo、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.05.018

  日期：2008.6

  The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst. (C) 2008 Elsevier Ltd. All rights reserved.
• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• Cuesta, Pedro J. Martinez de la; Martinez, Eloisa Rus; Sosa, Rafael Palomino, Anales de Quimica, 1995, vol. 91, # 1.2, p. 26 - 31
  作者：Cuesta, Pedro J. Martinez de la、Martinez, Eloisa Rus、Sosa, Rafael Palomino、Perez, Fuensanta I. Palomino

  DOI：——

  日期：——