4-(2-氧代吡咯烷-1-基)苯甲酸甲酯 | 221381-89-1

• 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: 4-(2-氧代吡咯烷-1-基)苯甲酸甲酯
• 中文别名: 4-(2-氧代-吡咯烷-1-基)-苯甲酸甲酯
• 英文名称: methyl 4-(2-oxopyrrolidin-1-yl)benzoate
• 英文别名: N-(4-methoxycarbonylphenyl)-2-pyrrolidinone；1-(4-methoxycarbonylphenyl)pyrrolidin-2-one
• CAS: 221381-89-1
• 化学式: C₁₂H₁₃NO₃
• mdl: MFCD00584781
• 分子量: 219.24
• InChiKey: DKZFCNDOGOKHQH-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• 沸点：
  447.6±28.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933790090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-(2-oxopyrrolidin-1-yl)benzoate
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: Methyl 4-(2-oxopyrrolidin-1-yl)benzoate
CAS number: 221381-89-1

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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: C12H13NO3
Molecular weight: 219.2

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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.

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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：

  4-(2-氧代吡咯烷-1-基)苯甲酸甲酯 在 palladium on activated charcoal nitronium tetrafluoborate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 10.0~25.0 ℃ 、206.84 kPa 条件下， 反应 7.0h， 生成 1-(4-methoxycarbonyl-2-aminophenyl)pyrrolidin-2-one
  参考文献：
  名称：

  含有2-吡咯烷酮取代基的苯甲酸能有效抑制流感病毒唾液酸酶。

  摘要：

  基于铅化合物4-（N-乙酰氨基）-3-胍基苯甲酸（BANA 113），其以2.5 microM的Ki抑制甲型流感唾液酸酶，设计了几种新型的唾液酸唾液酸酶芳香抑制剂。在这项研究中，BANA 113的N-乙酰基被2-吡咯烷酮环取代，该环的部分设计目的是为引入空间定向的侧链提供可能，该侧链可能与4-，5-和/或-相互作用唾液酸酶的6个亚位点。虽然母体结构1-（4-羧基-2-胍基苯基）吡咯烷-2--2-（8）只是适度的唾液酸酶抑制剂，但在2的C5'位置引入了羟甲基或双（羟甲基）取代基-吡咯烷酮环产生的微摩尔活性低的抑制剂（分别为9和12）。这些抑制剂与唾液酸酶复合的晶体结构表明2-吡咯烷酮环的5'-位的取代基在酶的4-和/或5-亚位相互作用。用疏水的3-戊基氨基取代12中的胍导致结合力大大增强，从而产生针对甲型流感病毒唾液酸酶的IC50约为50 nM的抑制剂（14），尽管对乙型流感病毒唾液酸酶的抑

  DOI：

  10.1021/jm980707k
• 作为产物：
  描述：

  4-(2-氧代-1-吡咯烷)-苯甲酸 在 硫酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以3.0 g (94%)的产率得到4-(2-氧代吡咯烷-1-基)苯甲酸甲酯
  参考文献：
  名称：

  Pyrrolidin-2-one compounds and their use as neuraminidase inhibitors

  摘要：

  具有以下化学式的化合物，其中所有变量均如规范中定义，用作神经氨酸酶抑制剂。

  公开号：

  US06509359B1

文献信息

• Rhodium(III)-Catalyzed C-H Vinylation of Arenes: Access to Functionalized Styrenes
  作者：Jun Zhou、Xin Li、Gang Liao、Bing-Feng Shi

  DOI：10.1002/cjoc.201800354

  日期：2018.12

  An effective method has been developed for Rh(III)‐catalyzed direct vinylation of arenes to give functionalized styrenes, using vinyltriethoxysilane as a convenient and inexpensive vinyl source. A wide variety of substrates, including 1‐aryl‐2‐pyrrolidinones, anilines, benzamides and ketones, were compatible with this reaction. Moreover, this method can be applied to the two‐step synthesis of functionalized

  已开发出一种有效的方法，可使用乙烯基三乙氧基硅烷作为方便，廉价的乙烯基来源，对Rh（III）催化的芳烃进行直接乙烯基化，以生成官能化的苯乙烯。此反应兼容多种底物，包括1-芳基-2-吡咯烷酮，苯胺，苯甲酰胺和酮。而且，该方法可以应用于功能化吲哚的两步合成。机理研究表明该反应可能通过氧化性Heck /去甲硅烷基化途径进行。
• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
  申请人：Bischoff Alexander

  公开号：US20100160323A1

  公开（公告）日：2010-06-24

  The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为硬脂酰辅酶A去饱和酶抑制剂的哌嗪衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• Interception of amide ylides with sulfonamides: synthesis of (<i>E</i>)-<i>N</i>-sulfonyl amidines catalyzed by Zn(OTf)₂
  作者：Jijun Chen、Wenhao Long、Shangwen Fang、Yonggang Yang、Xiaobing Wan

  DOI：10.1039/c7cc07364j

  日期：——

  Through the interception of amide ylides with sulfonamides, we herein report the first general example of an intermolecular condensation reaction between sulfonamides and amides. Beyond formamides, this approach was successfully applied to a variety of lactams and linear amides, giving rise to a broad array of (E)-N-sulfonyl amidines.

  通过用磺酰胺截留酰胺基化物，我们在此报道了磺酰胺和酰胺之间的分子间缩合反应的第一个一般实例。除甲酰胺外，该方法已成功应用于各种内酰胺和线性酰胺，从而产生了多种（E）-N-磺酰基am。
• Copper-Catalyzed N-Arylation of Amides Using (S)-N-Methylpyrrolidine-2-carboxylate as the Ligand
  作者：Chaoyu Wang、Lijuan Liu、Wei Wang、Dong-Sheng Ma、Hua Zhang

  DOI：10.3390/molecules15031154

  日期：——

  (S)-N-methylpyrrolidine-2-carboxylate, a derivative of natural L-proline, was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides with aryl halides under mild conditions. A variety of N-arylamides were synthesized in good to high yields.

  (S)-N-甲基吡咯烷-2-羧酸盐，一种天然L-脯氨酸的衍生物，发现它在温和条件下是铜催化的Goldberg型酰胺与芳基卤化物的N-芳基化反应的有效配体。合成了多种N-芳基酰胺，产率良好至高。