1-(3-氟苯基)-5-氧吡咯烷-3-羧酸 | 566154-63-0

• 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-(3-氟苯基)-5-氧吡咯烷-3-羧酸
• 中文别名: 1-(3-氟苯基)-5-氧代吡咯烷-3-甲酸
• 英文名称: 1-(3-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid
• CAS: 566154-63-0
• 化学式: C₁₁H₁₀FNO₃
• mdl: MFCD01569310
• 分子量: 223.204
• InChiKey: MIRPNVFOUKDBEF-UHFFFAOYSA-N

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-(3-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic 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: 1-(3-Fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid
CAS number: 566154-63-0

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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-(3-氟苯基)-5-氧吡咯烷-3-羧酸 在 sodium tetrahydroborate 、 氯化亚砜 、 lithium hydroxide monohydrate 、 偶氮二甲酸二异丙酯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 68.5h， 生成 8-{4-[1-(3-fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]phenyl}-1,3-dipropyl-3,7-dihydropurine-2,6-dione
  参考文献：
  名称：

  A 2B腺苷受体拮抗剂：新型黄嘌呤衍生物的设计，合成和生物学评估

  摘要：

  甲2BA Dor是低亲和力腺苷受体，通过GS功能介导的cAMP的升高和随后的下游信号传导。该受体与肺炎性疾病如COPD和哮喘有关。在文献中已经报道了几种有效的和选择性的A 2B AdoR拮抗剂，但是大多数化合物的药代动力学特性较差。因此，为了鉴定具有改善的药代动力学特性的新颖，有效和选择性的A 2B AdoR拮抗剂，我们首先探索了更受约束的MRS-1754形式（4）。为了改善代谢稳定性，尝试了几种接头修饰，以取代黄嘌呤头基的C8位和末端苯环之间的酰胺接头以及不同的苯基或其他杂芳基。SAR优化导致鉴定了两种新型A 2B AdoR拮抗剂，即8- {1- [5-Oxo-1-（4-三氟甲基-苯基）-吡咯烷-3-基甲基] -1H-吡唑-4-基} -1 ，3-二丙基-黄嘌呤（31）和8-（1- {2-氧代-2- [4-（3-三氟甲基-苯基）-哌嗪-1-基]-乙基} -1H-吡唑-4-基）-1,3-二丙

  DOI：

  10.1016/j.ejmech.2016.11.007
• 作为产物：
  描述：

  3-氟苯胺 、 衣康酸 在 sodium hydroxide 作用下， 反应 2.83h， 生成 1-(3-氟苯基)-5-氧吡咯烷-3-羧酸
  参考文献：
  名称：

  A 2B腺苷受体拮抗剂：新型黄嘌呤衍生物的设计，合成和生物学评估

  摘要：

  甲2BA Dor是低亲和力腺苷受体，通过GS功能介导的cAMP的升高和随后的下游信号传导。该受体与肺炎性疾病如COPD和哮喘有关。在文献中已经报道了几种有效的和选择性的A 2B AdoR拮抗剂，但是大多数化合物的药代动力学特性较差。因此，为了鉴定具有改善的药代动力学特性的新颖，有效和选择性的A 2B AdoR拮抗剂，我们首先探索了更受约束的MRS-1754形式（4）。为了改善代谢稳定性，尝试了几种接头修饰，以取代黄嘌呤头基的C8位和末端苯环之间的酰胺接头以及不同的苯基或其他杂芳基。SAR优化导致鉴定了两种新型A 2B AdoR拮抗剂，即8- {1- [5-Oxo-1-（4-三氟甲基-苯基）-吡咯烷-3-基甲基] -1H-吡唑-4-基} -1 ，3-二丙基-黄嘌呤（31）和8-（1- {2-氧代-2- [4-（3-三氟甲基-苯基）-哌嗪-1-基]-乙基} -1H-吡唑-4-基）-1,3-二丙

  DOI：

  10.1016/j.ejmech.2016.11.007

文献信息

• Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives
  作者：Vytautas Mickevičius、Rita Vaickelionienė、Ilona Jonuškienė、Gema Mikulskienė、Kristina Kantminienė

  DOI：10.1007/s00706-009-0201-z

  日期：2009.12

  AbstractCondensation of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carbohydrazides with aromatic aldehydes and acetone gave the corresponding hydrazones. Most of the reaction products are able to form isomers, because of the amide and azomethine structural units. The reactions of 1-aryl-4-hydrazinocarbonyl-2-pyrrolidinones with 2,4-pentanedione gave 3,5-dimethylpyrazole compounds

  摘要1-（3-（氟甲基和三氟甲基）苯基）-5-氧吡咯烷-3-碳酰肼与芳族醛和丙酮的缩合得到相应的。由于酰胺和偶氮甲碱的结构单元，大多数反应产物都能形成异构体。1-芳基-4-肼基羰基-2-吡咯烷酮与2，4-戊二酮的反应得到3，5-二甲基吡唑化合物，与2，5-己二酮的反应提供1-取代的2，5-二甲基吡咯。合成了几种恶二唑衍生物。基于它们的MS，IR，1 H和13 C NMR光谱以及通过分析方法来确认合成的化合物的结构。13 C APT，1 H / 13 C 2D（HETCOR）和NOE（1H）NMR技术和分子模型用于详细的结构检查。为了评估其构象，构型和取代基效应，对研究的化合物进行了完整的NMR光谱分配。 图形概要
• Pyrrolidone carboxamides
  申请人：Isler Markus

  公开号：US20050192292A1

  公开（公告）日：2005-09-01

  Pyrrolidone carboxamides of formula (I) where R 2 =a group of formula (a) or (b), R 5 =phenyl, heteroalkyl, aryloxy, alkoxy, alkanoyl or —NR 6 R 7 and R 1 , X, R 3 , R 4 , R 6 and R 7 have the meanings given in the description and the claims, pharmaceutically applicable acid addition salts with basic compounds of formula (I), pharmaceutically applicable salts of acid compounds of formula (I) with bases, pharmaceutically applicable esters of hydroxy- or carboxy-group containing compounds of formula (I) and hydrates and solvates thereof, inhibit the interaction of neuropeptide Y (NPY) with one of the neuropeptide receptor subtypes (NPY-Y5) and are particularly suitable for the prevention and treatment of arthritis, diabetes and especially eating disorders and obesity. The above can be produced by known methods and converted into a galenic dosage form.

  式 (I) 的吡咯烷酮羧酰胺，其中 R 2 =式 (a) 或 (b) 的基团，R 5 =苯基、杂烷基、芳氧基、烷氧基、烷酰基或-NR 6 R 7 和 R 1 ，X，R 3 , R 4 , R 6 和 R 7 具有在说明书和权利要求书中给出的含义；式(I)碱性化合物的药学上适用的酸加成盐；式(I)酸性化合物与碱的药学上适用的盐；含羟基或羧基的式(I)化合物的药学上适用的酯及其水合物和溶剂、抑制神经肽 Y（NPY）与一种神经肽受体亚型（NPY-Y5）的相互作用，特别适用于预防和治疗关节炎、糖尿病，尤其是进食障碍和肥胖症。上述药物可通过已知方法生产，并转化为半成品剂型。
• PYRROLIDON-CARBOXAMIDE
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1463724A1

  公开（公告）日：2004-10-06
• US7067549B2
  申请人：——

  公开号：US7067549B2

  公开（公告）日：2006-06-27
• [DE] PYRROLIDON-CARBOXAMIDE<br/>[EN] PYRROLIDONE CARBOXAMIDES<br/>[FR] CARBOXAMIDES DE PYRROLIDONE
  申请人：AXOVAN LTD

  公开号：WO2003059905A1

  公开（公告）日：2003-07-24

  Pyrrolidoncarboxamide der Formel (I) worin R2 einen Rest der Formel (a) oder (b) bedeutet, R5 Phenyl, Heteroalkyl, Aryloxy, Alkoxy, Alkanoyl oder -NR6R7 bedeutet und R?1, X, R3, R4, R6 und R7¿ die in der Beschreibung und den Ansprüchen definierte Bedeutung besitzen, pharmazeutisch verwendbare Säureadditionssalze von basischen Verbindungen der Formel (I), pharmazeutisch verwendbare Salze von sauren Verbindungen der Formel (I) mit Basen, pharmazeutisch verwendbare Ester von Hydroxy- oder Carboxygruppen enthaltenden Verbindungen der Formel (I) sowie Hydrate oder Solvate davon, hemmen die Interaktion des Neuropeptids Y (NPY) mit einem der Neuropeptid-Rezeptor-Subtypen (NPY-Y5) und eignen sich insbesondere für die Vorbeugung und Behandlung von Arthritis, Diabetes und speziell von Essstörungen und Obesitas. Sie können nach an sich bekannten Methoden hergestellt und in galenische Darreichungsformen gebracht werden.