phenylmethyl (R)-3-hydroxy-3-phenylpropanoate | 170108-73-3

• 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: phenylmethyl (R)-3-hydroxy-3-phenylpropanoate
• 英文别名: benzyl 3-hydroxy-3-phenylpropanoate；Benzyl 3-hydroxy-3-phenylpropionate；benzyl (3R)-3-hydroxy-3-phenylpropanoate
• CAS: 170108-73-3
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: BQRJXEZVPKQHMZ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  phenylmethyl (2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoate 在 aluminium amalgam 、 水 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 phenylmethyl (R)-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  A facile method for the synthesis of enantiopure α-unsubstituted β-hydroxy esters

  摘要：

  One-pot deacylation-debromination reactions involving the transesterification of the initial chiral beta-bromo-beta-hydroxy thioimide aldol adducts and subsequent Al-Hg mediated reductive cleavage of the C-Br bond allow for a facile synthesis of enantiopure beta-hydroxy esters. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00109-9

文献信息

• Dimethylzinc-Mediated, Oxidatively Promoted Reformatsky Reaction of Ethyl Iodoacetate with Aldehydes and Ketones
  作者：Pier Giorgio Cozzi、Alessandro Mignogna、Paola Vicennati

  DOI：10.1002/adsc.200700572

  日期：2008.5.5

  A practical and general Reformatsky reaction, promoted by oxidants and mediated by dimethylzinc, is described. The reaction is fast and runs at 0 °C with aldehydes and ketones, under mild reaction conditions. Preliminary results obtained for the enantioselective version show that inexpensive chiral amino alcohols could be used in the challenging formation of enantioenriched quaternary stereogenic centers

  描述了一种由氧化剂促进并由二甲基锌介导的实用且通用的Reformatsky反应。该反应快速，可在温和的反应条件下于0°C与醛和酮一起运行。对映体选择性形式获得的初步结果表明，廉价的手性氨基醇可用于富挑战性地形成对映体富集的季立体异构中心。
• An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(−)-epinephrine
  作者：Robert A. Singer、Erick M. Carreira

  DOI：10.1016/s0040-4039(96)02515-4

  日期：1997.2

  experimental procedure for the enantioselective, catalytic acetate aldol addition reaction. The addition of Me3SiCl and Et3N circumvents the azeotropic removal of the released isopropanol upon treating ligands 1 and 2 with Ti(OiPr)4. Importantly, this new procedure maintains the salient features of the catalytic process we originally described: high yields and enantioselectivities, low catalyst loads, and

  我们报道了催化剂3的原位制备，其实质上简化了对映选择性的，催化的乙酸酯羟醛加成反应的实验程序。Me 3 SiCl和Et 3 N的添加避免了用Ti（O i Pr）4处理配体1和2时共沸除去释放的异丙醇。重要的是，这种新方法保持了我们最初描述的催化过程的显着特征：高收率和对映选择性，低催化剂负载以及便捷的反应时间和温度。我们已将新程序应用于（R来自商业试剂的）-（-）-肾上腺素，总产率为45％。
• [2.2]Paracyclophane-based carbene–copper catalyst tuned by transannular electronic effects for asymmetric boration
  作者：Jianqiang Chen、Wenzeng Duan、Zhen Chen、Manyuan Ma、Chun Song、Yudao Ma

  DOI：10.1039/c6ra14404g

  日期：——

  of planar chiral carbene–copper complexes based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to asymmetric β-boration of α,β-unsaturated esters. As a result, transannular electronic effects of the substituent of the chiral catalyst have significant influence on the catalytic performance. A variety of chiral β-hydroxyl esters were obtained

  合成了一系列基于[2.2]对环环烷骨架并具有拟邻取代基的平面手性卡宾-铜配合物，并将其应用于α，β-不饱和酯的不对称β-硼酸酯化反应。结果，手性催化剂的取代基的跨环电子效应对催化性能具有显着影响。以优异的对映选择性（高达97％ee）和产率（高达99％）获得了各种手性β-羟基酯。
• Asymmetric aldol-type reaction between both achiral ketene silyl acetals of acetic acid esters and aldehydes by the use of a chiral promoter
  作者：Teruaki Mukaiyama、Shū Kobayashi、Tetsuya Sano

  DOI：10.1016/s0040-4020(01)85587-3

  日期：——

  aldol-type reaction between achiral ketene silyl acetals of acetic acid esters and achiral aldehydes is successfully carried out by the use of a chiral promoter, a combined use of chiral diamine coordinated tin(II) trifluoromethanesulfonate (tin(II) triflate) and tributyltin fluoride. The structure of this new promoter and the mechanism of the present asymmetric aldol-type reaction are discussed.

  通过使用手性促进剂，手性二胺配位的三氟甲磺酸锡（II）（三氟甲磺酸锡（II））和三丁基氟化锡。讨论了该新启动子的结构和当前不对称醛醇型反应的机理。
• Asymmetric Aldol-type Reaction between Both Achiral Ketene Silyl Acetals and Aldehydes by the Use of a Chiral Promoter
  作者：Shu Kobayashi、Tetsuya Sano、Teruaki Mukaiyama

  DOI：10.1246/cl.1989.1319

  日期：1989.8

  Highly enantioselective aldol-type reaction of achiral ketene silyl acetals with achiral aldehydes is carried out by the use of a chiral promoter, a combined use of chiral diamine coordinated tin(II) triflate and tributyltin fluoride.

  通过使用一个手性促剂，采用手性二胺配位的锡(II)三氟甲烷磺酸盐和三丁基锡氟化物的联合使用，进行非手性烯酮硅酸酯与非手性醛的高对映选择性醛醇反应。