1-(2-氟苯基)-5-氧代吡咯烷-3-羧酸 | 1998-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(2-氟苯基)-5-氧代吡咯烷-3-羧酸
• 英文名称: 1-(2-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid
• 英文别名: 4-carboxy-1-(2-fluorophenyl)-2-pyrrolidinone
• CAS: 1998-86-3
• 化学式: C₁₁H₁₀FNO₃
• mdl: MFCD01330894
• 分子量: 223.204
• InChiKey: SPNFIZUVZRKIQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  487.2±40.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(2-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid
Synonyms: 1-(2-Fluorophenyl)-2-pyrrolidinone-4-carboxylic acid

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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: 1-(2-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid
CAS number: 1998-86-3

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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.
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: C11H10FNO3
Molecular weight: 223.2

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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, nitrogen oxides, 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：

  1-(2-氟苯基)-5-氧代吡咯烷-3-羧酸 、 邻苯二胺 以 盐酸 为溶剂， 反应 24.0h， 以21%的产率得到4-(1H-benzimidazol-2-yl)-1-(2-fluorophenyl)-2-pyrrolidinone
  参考文献：
  名称：

  Cyclization products of N-fluorophenyl-β-alanines and their properties

  摘要：

  DOI：

  10.1007/s10593-006-0157-4
• 作为产物：
  描述：

  2-氟苯胺 、 衣康酸 生成 1-(2-氟苯基)-5-氧代吡咯烷-3-羧酸
  参考文献：
  名称：

  N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators

  摘要：

  A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.094

文献信息

• Studies on structural requirements for atropisomerism in N -phenyl γ-lactams
  作者：Xiaohua Sun、Minxiong Li、Mingming Sun、Xiaobo Li、Brian J. Xi、Yanjun Wu、Jia Yao、Zeping Zhan、Xu Bai、Ning Xi

  DOI：10.1016/j.tet.2018.04.090

  日期：2018.6

  conformational data derived from crystal structures showed that conformational variations in the γ-lactam ring had negligible impacts on the rotational barriers of the N-phenyl group around the central CN bond. Atropisomerism in N-phenyl γ-lactams was depended solely on the steric interactions between bulky ortho-substituents on the N-phenyl group and the adjacent CH2 and CO groups in the γ-lactam.

  我们制备了一系列取代的N-苯基γ-内酰胺，以研究形成阻转异构体的结构要求。NMR光谱和X射线晶体学数据以及手性HPLC分析证明，邻-F，Cl-二取代的N-苯基γ-内酰胺（即RS-4和SS-4）产生可分离的阻转异构体。使用源自晶体结构的构象数据进行的计算研究表明，γ-内酰胺环中的构象变化对中心C N键周围的N-苯基基团的旋转势垒的影响可忽略不计。N中的对映异构-苯基γ-内酰胺仅取决于N-苯基上的大体积邻位取代基与γ-内酰胺中相邻的CH 2和CO基团之间的空间相互作用。
• N-Aryl pyrrolidinonyl oxadiazoles as potent mGluR5 positive allosteric modulators
  作者：Mathivanan Packiarajan、Christine G. Mazza Ferreira、Sang-Phyo Hong、Andrew D. White、Gamini Chandrasena、Xiaosui Pu、Robbin M. Brodbeck、Albert J. Robichaud

  DOI：10.1016/j.bmcl.2012.06.094

  日期：2012.9

  A novel series of N-aryl pyrrolidinonyl oxadiazoles were identified as mGluR5 positive allosteric modulators (PAMs). Optimization of the initial lead compound 6a led to the identification of the 12c (-) enantiomer as a potent compound with acceptable in vitro clearance, CYP, hERG and PK properties. Para substituted N-aryl pyrrolidinonyl oxadiazoles are mGluR5 PAMs while the meta and ortho substituted N-aryl pyrrolidinonyl oxadiazoles are negative allosteric modulators (NAMs). Para fluoro substitution on the N-aryl group and meta chloro or methyl substituents on the aryl oxadiazole moiety are optimal for mGluR5 PAM efficacy. The existence of an exquisitely sensitive 'PAM to NAM switch' within this chemotype making it challenging for simultaneous optimization of potency and drug-like properties. (C) 2012 Elsevier Ltd. All rights reserved.
• Cyclization products of N-fluorophenyl-β-alanines and their properties
  作者：R. Vaickelioniene、V. Mickevicius

  DOI：10.1007/s10593-006-0157-4

  日期：2006.6