1-甲基-2-氧代吡咯烷-4-甲酸 | 42346-68-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 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-甲基-2-氧代吡咯烷-4-甲酸
• 中文别名: N-甲基吡啶-5-酮-3-甲酸；1-甲基-5-氧代-3-吡咯烷羧酸
• 英文名称: 1-methyl-5-oxopyrrolidine-3-carboxylic acid
• 英文别名: N-methyl-2-pyrrolidone-4-carboxylic acid
• CAS: 42346-68-9
• 化学式: C₆H₉NO₃
• mdl: MFCD00014102
• 分子量: 143.142
• InChiKey: YHDZDIPQCVCIJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933790090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-Methyl-5-oxo-pyrrolidine-3-carboxylic acid
Synonyms: 1-Methyl-2-pyrrolidinone-4-carboxylic acid

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-Methyl-5-oxo-pyrrolidine-3-carboxylic acid
CAS number: 42346-68-9

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C6H9NO3
Molecular weight: 143.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-甲基-2-氧代吡咯烷-4-甲酸 在 sodium hydroxide 、 sodium hydride 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 2-{[(1-methyl-5-oxopyrrolidin-3-yl)carbonyl]-anilino}acetic acid
  参考文献：
  名称：

  CCR5 Antagonists as Anti-HIV-1 Agents. 1. Synthesis and Biological Evaluation of 5-Oxopyrrolidine-3-carboxamide Derivatives

  摘要：

  一种新型的铅化合物N-{3-[4-(4-氟苯甲酰)piperidin-1-基]丙基}-1-甲基-5-氧代-N-苯基吡咯烷-3-羧酰胺（1）通过高通量筛选与[125I]RANTES和CCR5表达的CHO细胞被鉴定为CCR5拮抗剂。化合物1的IC50值为1.9 μM。为了提高化合物1的结合亲和力，合成了一系列5-氧代吡咯烷-3-羧酰胺。向中心苯环引入3,4-二氯取代基（10i，IC50=0.057 μM；11b，IC50=0.050 μM）或用1-苄基取代5-氧代吡咯烷部分的1-甲基基团（12e，IC50=0.038 μM）被发现有效提高了对CCR5的亲和力。化合物10i、11b和12e也分别以0.44、0.19和0.49 μM的IC50值抑制了CCR5使用的HIV-1包膜介导的膜融合。

  DOI：

  10.1248/cpb.52.63
• 作为产物：
  描述：

  1-甲基-5-氧代吡咯烷-3-羧酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以91%的产率得到1-甲基-2-氧代吡咯烷-4-甲酸
  参考文献：
  名称：

  Synthetic approaches to 10-azaprostaglandins

  摘要：

  DOI：

  10.1021/jo01293a010
• 作为试剂：
  描述：

  衣康酸 、 甲胺 、 1-甲基-2-氧代吡咯烷-4-甲酸 在 1-甲基-2-氧代吡咯烷-4-甲酸 、 乙酸乙酯 作用下， 以 水 为溶剂， 反应 1.0h， 以was obtained in the form of colorless crystals (yield: 59 g, 67%)的产率得到Itaconic Acid Methylamine
  参考文献：
  名称：

  MIXTURES OF ITACONIC ACID OR ITACONIC ACID DERIVATIVES AND PRIMARY AMINES FOR PRODUCING 1,3- AND 1,4-ALKYL METHYL PYRROLIDONES

  摘要：

  本发明涉及一种混合物，包括顺丁烯二酸或顺丁烯二酸衍生物和式（I）的一种一级胺，其中一级胺与顺丁烯二酸或顺丁烯二酸衍生物的摩尔比在0.5:1到20:1范围内，其中混合物中包含50摩尔百分比或更少的式（II）的4-羧基吡咯酮，式（II）的衍生物和式（III）的4-氨基甲酰基吡咯酮，基于所使用的顺丁烯二酸或顺丁烯二酸衍生物，其中R是具有1到24个碳原子的线性或支链饱和脂肪基或具有3到24个碳原子的饱和环脂肪基。本发明进一步提供了使用本发明混合物制备1,3-烷基甲基吡咯烷酮和/或1,4-烷基甲基吡咯烷酮的用途，以及制备1,3-烷基甲基吡咯烷酮和/或1,4-烷基甲基吡咯烷酮的方法。此外，本发明涉及包含1,3-烷基甲基吡咯烷酮和/或1,4-烷基甲基吡咯烷酮和1,3-烷基甲基吡咯烷的混合物，其中1,3-烷基甲基吡咯烷的比例在10到10,000 ppm范围内，并且涉及包含1,3-烷基甲基吡咯烷酮和1,4-烷基甲基吡咯烷酮的混合物，其中1,3-烷基甲基吡咯烷酮与1,4-烷基甲基吡咯烷酮的摩尔比在1:1到10:1范围内。

  公开号：

  US20110251119A1

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015180612A1

  公开（公告）日：2015-12-03

  Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

  揭示了新型视黄醇相关孤儿受体γ（RORγ）调节剂及其在通过RORγ介导的疾病治疗中的应用。
• [EN] AZETIDIN-3-YLMETHANOL DERIVATIVES AS CCR6 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS D'AZÉTIDIN-3-YLMÉTHANOL EN TANT QUE MODULATEURS DU RÉCEPTEUR CCR6
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2021219849A1

  公开（公告）日：2021-11-04

  The present invention relates to compounds of Formula (I), their synthesis and use as CCR6 receptor modulators for the treatment or prevention of various diseases, conditions or disorders.

  本发明涉及式(I)化合物，其合成以及作为CCR6受体调节剂用于治疗或预防各种疾病、状况或障碍。
• 1-alkyl-5-oxopyrrolidine-3-carboxylic esters with improved biodegradability
  申请人：Clariant Finance (BVI) Limited

  公开号：US08067651B2

  公开（公告）日：2011-11-29

  The invention provides compounds of the formula 1 in which A is a C2- to C4-alkylene group x is from 1 to 100 R1 is C1-C30-alkyl, C2-C30-alkenyl, C7-C30-alkylaryl R2 is an aliphatic, cycloaliphatic or aromatic radical which contains at least one structural unit of the formula 2  and y is from 0 to 100, with the proviso that y is from 1 to 100 when R2 is of the formula 2, and their use in amounts of from 0.01 to 2% by weight for preventing the formation of gas hydrates in aqueous phases which are in contact with a gaseous, liquid or solid organic phase.

  这项发明提供了以下式1的化合物 其中 A是一个C2到C4的烷基烯基 x为1至100 R1是C1-C30烷基，C2-C30烯基，C7-C30烷基芳基 R2是含有至少一个以下式2结构单元的脂肪、环脂肪或芳香基团 并且 y为0至100， 但要求当R2为式2时，y为1至100，并且它们在与气态、液态或固态有机相接触的水相中以0.01至2%的重量使用，以防止气体水合物的形成。
• [EN] 2-CYANOISOINDOLINE DERIVATIVES FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 2-CYANOISOINDOLINE POUR LE TRAITEMENT DU CANCER
  申请人：MISSION THERAPEUTICS LTD

  公开号：WO2017158388A1

  公开（公告）日：2017-09-21

  The invention relates to novel compounds of formula I which are inhibitors of deubiquitylating enzymes (DUBs) and/or desumoylating enzymes. In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 7 or ubiquitin specific peptidase 7 (USP7). The invention further relates to methods for the preparation of these compounds and to their use in the treatment of cancer.

  这项发明涉及公式I的新化合物，这些化合物是去泛素化酶（DUBs）和/或去泛素化酶的抑制剂。具体来说，该发明涉及抑制泛素C端水解酶7或泛素特异性肽酶7（USP7）。该发明还涉及这些化合物的制备方法以及它们在癌症治疗中的应用。
• NEW COMPOUNDS
  申请人：HAUEL Norbert

  公开号：US20100240669A1

  公开（公告）日：2010-09-23

  The present invention relates to the compounds of general formula I wherein n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and X are defined as described hereinafter, the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases, which have valuable properties, the preparation thereof, the medicaments containing the pharmacologically effective compounds, the preparation thereof and the use thereof.

  本发明涉及一般式I的化合物，其中n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和X的定义如下所述，其对映体、非对映体、混合物及其盐，特别是其与有机或无机酸或碱形成的生理上可接受的盐，具有有价值的性质，其制备方法，含有药理学有效化合物的药物，其制备方法和用途。