Acetic acid (R)-1-methyl-2-phenyl-allyl ester | 129571-70-6

• 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: Acetic acid (R)-1-methyl-2-phenyl-allyl ester
• 英文别名: [(2R)-3-phenylbut-3-en-2-yl] acetate
• CAS: 129571-70-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: XUBBVGOMZDNLGT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  magnesium,ethenylbenzene,bromide 在 RuCl(CO)2(η⁵-C5Ph5) Candida antarctica lipase B 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 Acetic acid (R)-1-methyl-2-phenyl-allyl ester
  参考文献：
  名称：

  烯丙醇的化学酶动力学动力学拆分：乙酰乙酸甘油酯的高度对映选择性的途径。

  摘要：

  用南极假丝酵母脂肪酶B（CALB）和钌催化剂1进行了一系列位阻烯丙基醇的动态动力学拆分（DKR）。将得到的光学纯净的烯丙基乙酸酯进行氧化裂解，以高产率得到相应的酰化酰化酰胆碱。不会丢失手性信息。

  DOI：

  10.1021/ol071395v

文献信息

• Nonenzymatic kinetic resolution of α-aryl substituted allylic alcohols catalyzed by acyl transfer catalyst Np-PIQ
  作者：Shan-Shan Jiang、Bo-Qi Gu、Ming-Yu Zhu、Xingxin Yu、Wei-Ping Deng

  DOI：10.1016/j.tet.2015.01.018

  日期：2015.2

  Chiral alpha-aryl substituted allylic alcohols are important versatile synthetic intermediates. We report here an effective nonenzymatic kinetic resolution of racemic alpha-aryl substituted allylic alcohols by introducing different aryl groups with acyl transfer catalyst Np-PIQ and propionic anhydride, providing moderate to good selectivity factors (S=12-37). (C) 2015 Elsevier Ltd. All rights reserved.
• Kinetic resolutions of chiral unsaturated alcohols that cannot be resolved efficiently via enantioselective epoxidation
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00176a076

  日期：1990.9
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.