(±)-扁桃-2,3,4,5,6-d5酸 | 70838-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (±)-扁桃-2,3,4,5,6-d5酸
• 中文别名: 苦杏仁酸-D5
• 英文名称: (RS)-2-hydroxy-2-(D₅)phenylacetic acid
• 英文别名: (RS)-mandelic acid-d₅；Mandelsaeure-；hydroxy-pentadeuteriophenyl-acetic acid；d₅-mandelic acid；(+/-)-Mandelic-2,3,4,5,6-d5 Acid；2-hydroxy-2-(2,3,4,5,6-pentadeuteriophenyl)acetic acid
• CAS: 70838-71-0
• 化学式: C₈H₈O₃
• 分子量: 157.11
• InChiKey: IWYDHOAUDWTVEP-RALIUCGRSA-N

物化性质

• 熔点：
  120-121 °C(Solv: benzene (71-43-2); ethanol (64-17-5))
• 溶解度：
  DMSO（微溶）、乙酸乙酯（微溶）、甲醇（微溶）、水（微溶、

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-扁桃-2,3,4,5,6-d5酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Preparation of (−)-(R)-2-(2,3,4,5,6-pentafluorophenoxy)-2-(phenyl-d5)acetic acid: an efficient 1H NMR chiral solvating agent for direct enantiomeric purity evaluation of quinoline-containing antimalarial drugs

  摘要：

  The title compound was prepared as a racemate from (+/-)-mandelic acid-d(5) in one step. The corresponding (-)-(R)-enantiomer (98% ee) was obtained by resolution with (-)-(R)-1-phenylethylamine and evaluated as a chiral solvating agent (CSA) for direct H-1 NMR enantiomeric excess determination of mefloquine (Lariam (R), chloroquine (Chloroquine Bayer (R)), and hydroxychloroquine (Plaquenil (R)) enantiomers. The displayed non-equivalence was high for signals in the aromatic region of all three antimalarials. Thus, the mandelic acid derivative described herein may be considered as the first efficient CSA 'invisible' in the aromatic region, useful for direct H-1 NMR ee value determination of chiral quinoline-containing antimalarial drugs. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.007
• 作为产物：
  描述：

  Ethylmandelat- 在 lithium hydroxide 作用下， 反应 0.17h， 生成 (±)-扁桃-2,3,4,5,6-d5酸
  参考文献：
  名称：

  扁桃酸衍生物的受控间位选择性 C–H 单烯烃和二烯烃

  摘要：

  扁桃酸代表了许多药物分子中存在的关键结构基序。在此，我们通过精心设计的底物和氧化剂报告了扁桃酸的受控间位选择性单烯和二烯化。此外，通过在温和的碱性条件下选择性去除模板，产生游离的间位官能化扁桃酸。证明了功能化可马托品和环兰地酯药物衍生物的合成。动力学同位素效应显示 C-H 活化是限速步骤。

  DOI：

  10.1021/acs.orglett.1c02080

文献信息

• SUBSTITUTED PHENYLCYCLOHEXYLGLYCOLATES
  申请人：Gant Thomas G.

  公开号：US20090247628A1

  公开（公告）日：2009-10-01

  Disclosed herein are substituted phenylcyclohexylglycolate-based muscarinic acetylcholine receptor modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

  本文揭示了基于取代苯基环己基甘醇酸酯的 Formula I 的肌氨酸乙酰胆碱受体调节剂，其制备方法、药物组合物及使用方法。
• BTEX METABOLITES DERIVATIZATION KIT AND COMPOSITION
  申请人：Board of Regents, The University of Texas System

  公开号：US20190346449A1

  公开（公告）日：2019-11-14

  A kit or composition for in situ simultaneously derivatization of 14 phenol and carboxylic acid metabolites of benzene, toluene, ethylbenzene, and xylene (BTEX) in a urine sample is disclosed. The derivatization imparts a positive charge to phenol and carboxylic acid for subsequent LC-MS analysis. Limit of detection reached part-per-trillion levels for o-Cresol and part-per-billion levels for the remaining BTEX metabolites. BTEX metabolites can be detected in less than 35 mins according to one embodiment of the invention. Methods, kits and compositions disclosed herein can be used for in situ simultaneous derivatization of phenol and carboxylic acid in aqueous solution in general.

  本文介绍了一种针对尿样中苯、甲苯、乙苯和二甲苯（BTEX）的14种酚和羧酸代谢物的原位同时衍生化试剂盒或组合物。衍生化使酚和羧酸带有正电荷，以便进行后续的LC-MS分析。对于o-甲酚，检测限达到了每万亿级别，对于其余的BTEX代谢物，检测限达到了每十亿级别。根据本发明的一种实施方式，BTEX代谢物可以在不到35分钟内被检测到。本文所披露的方法、试剂盒和组合物可用于一般水溶液中酚和羧酸的原位同时衍生化。
• ANDRESEN B. D.; WEITZENKORN D. E., J. LABELLED COMPOUNDS AND RADIOPHARM., 1978, 15, 469-478
  作者：ANDRESEN B. D.、 WEITZENKORN D. E.

  DOI：——

  日期：——
• [EN] BTEX METABOLITES DERIVATIZATION KIT AND COMPOSITION<br/>[FR] KIT ET COMPOSITION DE DÉRIVATISATION DE MÉTABOLITES DE BENZÈNE, TOLUÈNE, ÉTHYLBENZÈNE ET XYLÈNE
  申请人：UNIV TEXAS

  公开号：WO2017214549A1

  公开（公告）日：2017-12-14

  A kit or composition for in situ simultaneously derivatization of 14 phenol and carboxylic acid metabolites of benzene, toluene, ethylbenzene, and xylene (BTEX) in a urine sample is disclosed. The derivatization imparts a positive charge to phenol and carboxylic acid for subsequent LC-MS analysis. Limit of detection reached part-per-trillion levels for o-Cresol and part-per-billion levels for the remaining BTEX metabolites. BTEX metabolites can be detected in less than 35 mins according to one embodiment of the invention. Methods, kits and compositions disclosed herein can be used for in situ simultaneous derivatization of phenol and carboxylic acid in aqueous solution in general.
• Controlled <i>meta</i>-Selective C–H Mono- and Di-Olefination of Mandelic Acid Derivatives
  作者：Perumal Muthuraja、Rahamdil Usman、Revathy Sajeev、Purushothaman Gopinath

  DOI：10.1021/acs.orglett.1c02080

  日期：2021.8.6

  Mandelic acids represent a key structural motif present in many drug molecules. Herein, we report the controlled meta-selective mono- and diolefination of mandelic acids by the careful design of the substrate and oxidant. Furthermore, free meta-functionalized mandelic acid was generated by selectively removing the template under mild basic conditions. The synthesis of functionalized homatropine and

  扁桃酸代表了许多药物分子中存在的关键结构基序。在此，我们通过精心设计的底物和氧化剂报告了扁桃酸的受控间位选择性单烯和二烯化。此外，通过在温和的碱性条件下选择性去除模板，产生游离的间位官能化扁桃酸。证明了功能化可马托品和环兰地酯药物衍生物的合成。动力学同位素效应显示 C-H 活化是限速步骤。