(-)-(R)-O-pentafluorophenyl mandelic acid | 1196831-52-3

• 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: (-)-(R)-O-pentafluorophenyl mandelic acid
• 英文别名: (-)-(2R)-2-(pentafluorophenoxy)-2-phenylacetic acid；(2R)-2-(2,3,4,5,6-pentafluorophenoxy)-2-phenylacetic acid
• CAS: 1196831-52-3
• 化学式: C₁₄H₇F₅O₃
• 分子量: 318.2
• InChiKey: FOYPKWRFUOPTDC-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-(R)-O-pentafluorophenyl mandelic acid 、 octahydro-4,8;6,9a-dimethano-cyclooctaoxazol-2-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.0h， 以42%的产率得到
  参考文献：
  名称：

  三氟甲磺酸促进金刚烷-恶唑烷-2-one的脱羧：获得手性胺和杂环。

  摘要：

  我们已经通过金刚烷-恶唑烷-2-one的脱羧作用，对多种手性亲脂性和构象刚性的胺和杂环开发了一步式方法。三氟甲磺酸或三氟甲磺酸铝促进向恶唑烷-2-酮部分添加多种亲核试剂，同时释放出二氧化碳。然后将所得的胺或杂环通过催化剂质子化/金属化（助催化剂）。此外，使用手性助剂将外消旋原料金刚烷-恶唑烷-2-one拆分为单一对映异构体，以获取对映体富集的产物，并研究手性1,2-二取代的金刚烷衍生物的消旋途径。

  DOI：

  10.1021/acs.joc.7b00711
• 作为产物：
  描述：

  六氟苯 、 D-扁桃酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 丁腈 为溶剂， 反应 15.0h， 以9%的产率得到(-)-(R)-O-pentafluorophenyl mandelic acid
  参考文献：
  名称：

  One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents

  摘要：

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.002

文献信息

• One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents
  作者：Maria Maddalena Cavalluzzi、Claudio Bruno、Giovanni Lentini、Angelo Lovece、Alessia Catalano、Alessia Carocci、Carlo Franchini

  DOI：10.1016/j.tetasy.2009.08.002

  日期：2009.9

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.
• Triflic Acid Promoted Decarboxylation of Adamantane-oxazolidine-2-one: Access to Chiral Amines and Heterocycles
  作者：Radim Hrdina、Marta Larrosa、Christian Logemann

  DOI：10.1021/acs.joc.7b00711

  日期：2017.5.5

  one-step procedure to a variety of chiral lipophilic and conformationally rigid amines and heterocycles by decarboxylation of adamantane-oxazolidine-2-one. Triflic acid or aluminum triflate promote the addition of diverse nucleophiles to the oxazolidine-2-one moiety accompanied by the release of carbon dioxide. The resulting amine or heterocycle is then protonated/metalated by the catalyst (promotor). Additionally

  我们已经通过金刚烷-恶唑烷-2-one的脱羧作用，对多种手性亲脂性和构象刚性的胺和杂环开发了一步式方法。三氟甲磺酸或三氟甲磺酸铝促进向恶唑烷-2-酮部分添加多种亲核试剂，同时释放出二氧化碳。然后将所得的胺或杂环通过催化剂质子化/金属化（助催化剂）。此外，使用手性助剂将外消旋原料金刚烷-恶唑烷-2-one拆分为单一对映异构体，以获取对映体富集的产物，并研究手性1,2-二取代的金刚烷衍生物的消旋途径。