(R)-1-phenylpropyl isobutyrate

• 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-phenylpropyl isobutyrate
• 英文别名: [(1R)-1-phenylpropyl] 2-methylpropanoate
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: CEIYOQMOCDFZQO-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 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：

  4-nitrophenyl isobutyrate 、 1-苯丙醇 在 (C5Ph5)Ru(Cl)(CO)2 、 (2S,3R)-3,4-二氢-3-异丙基-2-苯基-2H-嘧啶并[2,1-b]苯并噻唑 、 potassium tert-butylate 、 potassium carbonate 作用下， 反应 72.0h， 以84%的产率得到(R)-1-phenylpropyl isobutyrate
  参考文献：
  名称：

  仲醇的酰基动力学动力学拆分：HyperBTM和贝克勒钌络合物的串联催化

  摘要：

  据报道，使用异硫脲衍生的HyperBTM催化剂，通过对映选择性酰化作用，仲醇的非酶动力学动力学拆分（DKR），以及由Bäckvall钌络合物使缓慢反应的醇外消旋化。DKR方法具有高对映选择性（高达99：1），采用易于处理的结晶异丁酸4-硝基苯基酯作为酰化剂，可在室温和环境气氛下进行。通过DFT计算，详细阐述了以阳离子化的HyperBTM催化剂与醇芳基亚基的π电子之间的阳离子-π系统相互作用为特征的立体诱导模型。

  DOI：

  10.1021/acs.joc.1c00545

文献信息

• Fluxionally Chiral DMAP Catalysts: Kinetic Resolution of Axially Chiral Biaryl Compounds
  作者：Gaoyuan Ma、Jun Deng、Mukund P. Sibi

  DOI：10.1002/anie.201406684

  日期：2014.10.27

  incorporate fluxional groups provide enhanced selectivity in asymmetric transformations? To address this issue, we have designed chiral 4‐dimethylaminopyridine (DMAP) catalysts with fluxional chirality. These catalysts were found to be efficient in promoting the acylative kinetic resolution of secondary alcohols and axially chiral biaryl compounds with selectivity factors of up to 37 and 51, respectively.

  包含助熔基团的有机催化剂能否在不对称转化中提供更高的选择性？为了解决这个问题，我们设计了具有手性手性的手性4-二甲基氨基吡啶（DMAP）催化剂。发现这些催化剂可有效提高仲醇和轴向手性联芳基化合物的酰基动力学分离度，选择性因子分别高达37和51。
• Kinetic Resolution of Secondary Carbinols by a Chiral<i>N</i>,<i>N</i>-4-Dimethylaminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Hydrogen Bonding Affects Catalytic Activity and Enantioselectivity
  作者：Kazuki Fujii、Koichi Mitsudo、Hiroki Mandai、Seiji Suga

  DOI：10.1246/bcsj.20160135

  日期：2016.9.15

  We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or

  我们使用具有叔醇取代基的联萘基 N,N-4-二甲氨基吡啶 (DMAP) 衍生物 1d 开发了仲甲醇的酰化动力学拆分。反应在范围广泛的甲醇中进行，具有中到高的选择性 (s)（高达 s = 79.5）。动力学研究表明，催化剂 1d 比相应的双甲基醚 1d' 或 DMAP 具有更高的催化活性。催化剂的叔醇和仲甲醇之间的氢键是提高反应速率和高对映选择性的原因。
• Two-Step Kinetic Resolution of Racemic Secondary Benzylic Alcohols Using the Combination of Enantioselective Silylation and Acylation: One-Pot Procedure Catalyzed by Chiral Guanidine
  作者：Kanako Miyazaki、Kenya Nakata

  DOI：10.1021/acs.joc.2c01129

  日期：2022.8.5

  A novel two-step kinetic resolution of racemic secondary benzylic alcohols with practical enantiomeric ratios was achieved. The reactions were carried out via a one-pot operation by combining enantioselective silylation and acylation mediated by the same chiral guanidine catalyst.

  实现了具有实用对映体比率的外消旋仲苄醇的新型两步动力学拆分。该反应通过一锅操作进行，通过组合对映选择性甲硅烷基化和由相同手性胍催化剂介导的酰化。
• Axially Chiral Analogues of 4-(Dimethylamino)pyridine:  Novel Catalysts for Nonenzymatic Enantioselective Acylations
  作者：Alan C. Spivey、Tomasz Fekner、Sharon E. Spey

  DOI：10.1021/jo0000574

  日期：2000.5.1

  A concise seven-step synthesis of atropisomeric S-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (+/-)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).
• Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst
  作者：Matthew R. Crittall、Henry S. Rzepa、David R. Carbery

  DOI：10.1021/ol2001705

  日期：2011.3.4

  The design, synthesis, and study of a helical dialkylaminopyridine Lewis base catalyst is reported. Helical DMAP analogue 4 is based upon a helicenoid structure and displays good to excellent levels of selectivity (S <= 116) in the kinetic resolution of chiral secondary alcohols. Catalyst 4 displays excellent reactivity with exceptionally low loadings of 0.05 mol % effecting practical levels of selectivity in kinetic resolutions.