(R)-2-氟扁桃酸 | 32222-48-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (R)-2-氟扁桃酸
• 中文别名: R-(-)-邻氟扁桃酸；D-邻氟扁桃酸；D-邻氟扁桃酸{R-(-)-邻氟扁桃酸、R-(-)-2-氟扁桃酸}；D-邻氟扁桃酸扁桃酸；R-(-)-2-氟扁桃酸
• 英文名称: (R)-2-(2-fluorophenyl)-2-hydroxyacetic acid
• 英文别名: R-ortho-fluoromandelic acid；(2R)-2-(2-fluorophenyl)-2-hydroxyacetic acid
• CAS: 32222-48-3
• 化学式: C₈H₇FO₃
• 分子量: 170.14
• InChiKey: WWSRHIZZWWDONI-SSDOTTSWSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  314.8±27.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  4

安全信息

• 海关编码：
  2918199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (R)-2-Fluoromandelic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (R)-2-Fluoromandelic acid
CAS number: 32222-48-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H7FO3
Molecular weight: 170.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-2-氟扁桃酸 生成 (2R)-2-(2-fluorophenyl)-2-hydroxy-N-[(3S)-1-(4-hydroxyphenyl)pentan-3-yl]acetamide
  参考文献：
  名称：

  MILLS, JACK;SCHMIEGEL, KLAUS K.;SHAW, WALTER N

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氟扁桃酸 在 (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB₅₀₇₄ 、 (S)-hydroxyacid dehydrogenase from Pseudomonas aeruginosa CCTCC M 2011394 、 甘油 作用下， 以 aq. phosphate buffer 为溶剂， 反应 25.0h， 以99.9%的产率得到
  参考文献：
  名称：

  通过串联生物催化氧化和还原反应对一锅一锅的2-羟基酸进行一步脱硫。

  摘要：

  通过将产生（S）-羟酸脱氢酶的微生物的静止细胞与（ R）-产生酮酸还原酶的微生物。

  DOI：

  10.1039/c3cc46240d
• 作为试剂：
  描述：

  1-(4-chlorobenzyl)-4-methyl-3-nitropyridin-1-ium bromide 、 苄叉丙酮 在 (R)-2-氟扁桃酸 、 C₂₃H₃₁N₃ 、 sodium acetate 作用下， 以 氯仿 为溶剂， 反应 60.0h， 以78%的产率得到
  参考文献：
  名称：

  N，4-二烷基吡啶鎓盐和烯酮的不对称脱芳族形式[4 + 2]环加成反应可构建阿扎比罗[5.5]十一烷骨架

  摘要：

  活化的N，4-二烷基吡啶鎓盐与无环的α，β-不饱和酮的不对称脱芳族形式[4 + 2]环加成反应是由金鸡纳胺的级联亚胺亚胺离子-烯胺催化而开发的。高效地构建了一系列有价值的氮杂螺[5.5]十一烷结构，具有很高的非对映选择性和对映选择性。

  DOI：

  10.1021/acs.orglett.8b03576

文献信息

• COFERONS AND METHODS OF MAKING AND USING THEM
  申请人：Barany Francis

  公开号：US20120295874A1

  公开（公告）日：2012-11-22

  The present invention is directed to a monomer useful in preparing therapeutic compounds. The monomer includes one or more pharmacophores which potentially binds to a target molecule with a dissociation constant of less than 300 μM and a linker element connected to the pharmacophore. The linker element has a molecular weight less than 500 daltons, is connected, directly or indirectly through a connector, to the pharmacophore.

  本发明涉及一种用于制备治疗性化合物的单体。该单体包括一个或多个可与目标分子结合的药效团，其解离常数小于300微摩尔，以及与药效团连接的连接元素。所述连接元素的分子量小于500道尔顿，通过直接连接或通过连接器间接与药效团相连。
• Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase
  作者：Ya-Ping Xue、Chuang Wang、Di-Chen Wang、Zhi-Qiang Liu、Yu-Guo Zheng

  DOI：10.1007/s12010-018-2760-0

  日期：2018.11

  coli (HADH-LlKAR-GDH) co-expressing 2-hydroxyacid dehydrogenase, LlKAR, and glucose dehydrogenase was constructed for efficient deracemization of racemic 2-HAs. Most of the racemic 2-HAs were deracemized to their (R)-isomers at high yields and enantiomeric purity. In the case of racemic 2-chloromandelic acid, as much as 300 mM of substrate was completely transformed into the optically pure (R)-2-chloromandelic

  对映纯2-羟基酸（2-HAs）是合成药物和精细化学品的重要中间体。外消旋2-HA脱硫成相应的单个对映体代表了一种工业上合成手性2-HA的经济高效的方法。在这项工作中，通过基因组挖掘发现了一种来自乳酸乳球菌（LlKAR）的新的酮酸还原酶，该酶具有更高的活性和对芳香族α-酮酸的底物耐受性，然后对其酶学性质进行了表征。因此，构建了共表达2-羟酸脱氢酶，LlKAR和葡萄糖脱氢酶的工程化大肠杆菌（HADH-L1KAR-GDH），以有效地消旋外消旋2-HA。大部分外消旋2-HA均以高收率和对映体纯度脱硫为它们的（R）异构体。
• The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation
  作者：Huan Guo、Jing Li、Delong Liu、Wanbin Zhang

  DOI：10.1002/adsc.201700846

  日期：2017.10.25

  A ruthenocenyl phosphino‐oxazoline‐ruthenium complex (RuPHOX−Ru) catalyzed asymmetric hydrogenation of α‐aryl keto acids has been successfully developed, affording the corresponding chiral α‐aryl α‐hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed

  已成功开发了钌烯基膦基-恶唑啉-钌络合物（RuPHOX-Ru）催化的α-芳基酮酸不对称氢化反应，可提供高收率和ee高达97％的相应手性α-芳基α-羟基羧酸。该反应可以在相对较低的催化剂负载量（至多5000 S / C）下以克为单位进行，所得产物可以转化为几种手性结构单元，生物活性化合物和手性药物。
• Phenethanolamines, compositions containing the same, and method for
  申请人：Eli Lilly and Company

  公开号：US04391826A1

  公开（公告）日：1983-07-05

  Optically active N-3-(4-substituted phenyl)propyl-.beta.-phenethanolamines are provided as well as pharmaceutical compositions containing such compounds. A method for effecting weight control in obese animals utilizing optically active phenethanolamines is disclosed. Novel intermediates useful in the preparation of optically active .beta.-phenethanolamines are provided.

  提供了具有光学活性的N-3-(取代苯基)丙基-β-苯乙醇胺，以及含有这类化合物的药物组合物。还揭示了利用具有光学活性的苯乙醇胺来实现肥胖动物体重控制的方法。提供了在制备具有光学活性的β-苯乙醇胺中有用的新型中间体。
• Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale
  作者：Hongxia Zhang、Shaixiao Tian、Yue Yue、Min Li、Wei Tong、Guangyu Xu、Bo Chen、Ming Ma、Yanwei Li、Jian-bo Wang

  DOI：10.1021/acscatal.9b04804

  日期：2020.3.6

  performance in the reactions of these substrates, while in silico calculations shed light on the origin of these improvements. Finally, 10 α-fluorocarboxylic acids and 10 α-hydroxycarboxylic acids were prepared on a gram scale via kinetic resolution enabled by WT, W185T, or W185N. This work expands the biocatalytic toolbox and allows a deep insight into the fluoroacetate dehalogenase catalyzed C–F cleavage

  在此，通过外消旋α-氟代羧酸的动力学拆分，探索了氟乙酸盐脱卤酶RPA1163的合成用途，用于生产对映体纯的（R）-α-氟代羧酸和（R）-α-羟基代羧酸。尽管野生型（WT）RPA1163显示出高的热稳定性和相当宽的底物范围，但仍然存在许多有趣但接受程度不高或中等的底物。为了解决该问题并发展规模化生产，采用了计算机模拟和半理性诱变。残基W185被设计用于丙氨酸，丝氨酸，苏氨酸或天冬酰胺。两种最佳的突变体W185N和W185T在这些底物的反应中表现出显着改善的性能，而在计算机上计算结果揭示了这些改进的起源。最后，通过WT，W185T或W185N实现的动力学拆分，以克为单位制备了10种α-氟代羧酸和10种α-羟基羧酸。这项工作扩展了生物催化工具箱，并允许深入了解氟乙酸盐脱卤酶催化的CF裂解机理。