[(2R)-1-phenylpropan-2-yl] propanoate | 116809-20-2

• 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: [(2R)-1-phenylpropan-2-yl] propanoate
• CAS: 116809-20-2
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: QTYQSMTXASOWLJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2R)-1-phenylpropan-2-yl] propanoate 在 sodium hydroxide 作用下， 反应 4.0h， 生成 (R)-1-苯基-2-丙醇
  参考文献：
  名称：

  Anhydrides as acylating agents in lipase-catalyzed stereoselective esterification of racemic alcohols

  摘要：

  DOI：

  10.1021/jo00258a024
• 作为产物：
  描述：

  1-苯基-2-丙醇 、 丙酸酐 以 苯 为溶剂， 反应 10.0h， 以39%的产率得到[(2R)-1-phenylpropan-2-yl] propanoate
  参考文献：
  名称：

  Anhydrides as acylating agents in lipase-catalyzed stereoselective esterification of racemic alcohols

  摘要：

  DOI：

  10.1021/jo00258a024

文献信息

• Acylative Kinetic Resolution of Alcohols Using a Recyclable Polymer-Supported Isothiourea Catalyst in Batch and Flow
  作者：Rifahath Mon Neyyappadath、Ross Chisholm、Mark D. Greenhalgh、Carles Rodríguez-Escrich、Miquel A. Pericàs、Georg Hähner、Andrew D. Smith

  DOI：10.1021/acscatal.7b04001

  日期：2018.2.2

  prepared and used for the acylative kinetic resolution of secondary alcohols. A wide range of alcohols, including benzylic, allylic, and propargylic alcohols, cycloalkanol derivatives, and a 1,2-diol, has been resolved using either propionic or isobutyric anhydride with good to excellent selectivity factors obtained (28 examples, s values up to 600). The catalyst can be recovered and reused by a simple filtration

  已经制备了基于均相催化剂HyperBTM的聚苯乙烯负载的异硫脲催化剂，并将其用于仲醇的酰基动力学拆分。宽范围的醇，包括苄基，烯丙基，和炔丙基醇，环烷醇衍生物，和1,2-二醇的，已使用或者丙酸或异丁酸酐以良好到获得优异的选择性因子（28个实施例中，解决了小号值最大为600）。催化剂可以通过简单的过滤和洗涤程序进行回收和再利用，而无需采取特殊的预防措施。证明了该催化剂的可回收性（15个循环），活性或选择性均无明显损失。可循环使用的催化剂还用于使用不同的酸酐顺序拆分10种不同的醇，各循环之间无交叉污染。最后，在连续流工艺中的成功应用证明了用于流态醇动力学分离的固定化Lewis碱催化剂的第一个实例。
• Homobenzotetramisole:  An Effective Catalyst for Kinetic Resolution of Aryl-Cycloalkanols
  作者：Vladimir B. Birman、Ximin Li

  DOI：10.1021/ol703119n

  日期：2008.3.1

  Homobenzotetramisole (HBTM), a ring-expanded analogue of the previously reported catalyst BTM, displays higher catalytic activity and a different structure-selectivity profile. It displays good enantioselectivities in kinetic resolution of secondary benzylic alcohols but is particularly effective for 2-aryl-substituted cycloalkanols.
• Kinetic Resolution of Secondary Alcohols Using Amidine-Based Catalysts
  作者：Ximin Li、Hui Jiang、Eric W. Uffman、Lei Guo、Yuhua Zhang、Xing Yang、Vladimir B. Birman

  DOI：10.1021/jo202220x

  日期：2012.2.17

  Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.
• Horiuchi, Kenichi; Kobashi, Kazunori; Nagata, Hidetomo, Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 7, p. 1330 - 1331
  作者：Horiuchi, Kenichi、Kobashi, Kazunori、Nagata, Hidetomo、Satoh, Toshinobu、Suemitsu, Rikisaku

  DOI：——

  日期：——
• Activity enhancement of pig liver esterase in organic solvents by colyophilization with methoxypolyethylene glycol: kinetic resolution of alcohols
  作者：Stephan Ruppert、Hans-Joachim Gais

  DOI：10.1016/s0957-4166(97)00469-2

  日期：1997.11

  Colyophilization of pig liver esterase with methoxypolyethylene glycol gave a catalyst, PLE/MPEG, which showed an enhanced activity in organic solvents. The PLE/MPEG catalyzed transesterification of the alcohols rac-1a-d with vinyl propionate in toluene proceeded with good to high selectivities. The addition of up to 1% of water to the reaction mixture resulted in a significant increase in enantioselectivity. Immobilization of PLE/MPEG for the batch-wise resolution was accomplished by its spontaneous adsorption on an ultrafiltration membrane. (C) 1997 Elsevier Science Ltd.