2-氧代-2,5-二氢-吡咯-1-羧酸叔丁酯 | 141293-14-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 2-氧代-2,5-二氢-吡咯-1-羧酸叔丁酯
• 中文别名: N-Boc-2,5-二氢-吡咯-2-酮；N-(叔丁氧羰基)-3-吡咯啉-2-酮
• 英文名称: N-(tert-butoxycarbonyl)pyrrol-2(5H)-one
• 英文别名: tert-butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate；N-boc-3-pyrrolin-2-one；tert-butyl 5-oxo-2H-pyrrole-1-carboxylate
• CAS: 141293-14-3
• 化学式: C₉H₁₃NO₃
• mdl: MFCD01318910
• 分子量: 183.207
• InChiKey: MFJKZXLOHPVLBS-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68℃
• 沸点：
  241.8±33.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  室温和干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
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: 2-Oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester
CAS number: 141293-14-3

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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: C9H13NO3
Molecular weight: 183.2

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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

制备方法与用途

2-氧代-2,5-二氢-吡咯-1-羧酸叔丁酯是一种杂环化合物，主要用于实验室研发和化工医药合成过程。

反应信息

• 作为反应物：
  描述：

  2-氧代-2,5-二氢-吡咯-1-羧酸叔丁酯 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以45%的产率得到tert-butyl [(5-oxopyrazolidin-3-yl)methyl]carbamate
  参考文献：
  名称：

  新型3D丰富的α-氨基酸衍生的3-吡唑烷酮的合成

  摘要：

  研究了在位置N（1）和/或C（5）上官能化的新型3-吡唑烷酮衍生物的合成方法。由N-保护的甘氨酸通过Masamune-Claisen同源化，还原，O-甲磺酰化和与肼衍生物的环化反应，在四个步骤中制备5-氨基烷基-3-吡唑烷酮。通过酸解脱保护制备游离胺。还通过用水合肼对N-Boc-吡咯啉-2（5H）-1进行“环切换”转化来制备标题化合物。对5-（N-烷基-N-Cbz-氨基甲基）吡唑烷-3-酮进行氢解脱保护，然后与1,1'-羰基二咪唑（CDI）环合，得到两个新的全氢咪唑并[1,5-b]吡唑代表，是几乎未开发的杂环系统。3-氧代吡唑烷-5-羧酸的酰胺化以中等收率得到相应的羧酰胺。由（S）-AlaOMe和（S）-ProOMe获得的非对映体非外消旋羧酰胺通过MPLC分离。

  DOI：

  10.17344/acsi.2017.3438
• 作为产物：
  描述：

  tert-butyl N-acryloyl-N-(prop-2-en-1-yl)carbamate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以83%的产率得到2-氧代-2,5-二氢-吡咯-1-羧酸叔丁酯
  参考文献：
  名称：

  闭环易位的α，β-不饱和内酰胺的简便方法

  摘要：

  在此报道了通过容易制备的二烯酰胺的闭环易位合成α，β-不饱和内酰胺的简便有效的策略。优化了反应条件以使二烯酰胺进行易位环化，以良好至极好的收率获得五元至七元的未取代和β-取代的α，β-不饱和内酰胺。

  DOI：

  10.1007/s10593-016-1858-y

文献信息

• (Indazol-4-YL) Hexahydropyrrolopyrrolones and Methods of Use
  申请人：AbbVie Inc.

  公开号：US20160264582A1

  公开（公告）日：2016-09-15

  Compounds of formula (I) and pharmaceutically acceptable salts, esters, amides, or radiolabelled forms thereof, wherein G Ar , L 1 , Z 1 and Z 2 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by voltage-gated sodium channels, e.g., Na v 1.7 and/or Na v 1.8. Methods for making the compounds are disclosed. Also disclosed are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

  式（I）的化合物及其药用可接受的盐、酯、酰胺或放射标记形式，其中G、Ar、L1、Z1和Z2如规范中所定义，可用于治疗由电压门控钠通道如Na v 1.7和/或Na v 1.8预防或改善的病症或紊乱。公开了制备这些化合物的方法。还公开了式（I）化合物的药物组合物，以及使用这些化合物和组合物的方法。
• [EN] TRIAZOLOPYRIDINE INHIBITORS OF MYELOPEROXIDASE<br/>[FR] INHIBITEURS, À BASE DE TRIAZOLOPYRIDINE, DE LA MYÉLOPEROXYDASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2017040449A1

  公开（公告）日：2017-03-09

  The present invention provides compounds of Formula (I): wherein A is as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, which may be used as medicaments.

  本发明提供了化合物的结构式（I）：其中A如规范中定义，并包括任何此类新化合物的组合物。这些化合物是髓过氧化物酶（MPO）抑制剂和/或嗜酸性粒细胞过氧化物酶（EPX）抑制剂，可用作药物。
• Substituted Indazoles as Na_v1.7 Blockers for the Treatment of Pain
  作者：Jennifer M. Frost、David A. DeGoey、Lei Shi、Rebecca J. Gum、Meagan M. Fricano、Greta L. Lundgaard、Odile F. El-Kouhen、Gin C. Hsieh、Torben Neelands、Mark A. Matulenko、Jerome F. Daanen、Madhavi Pai、Nayereh Ghoreishi-Haack、Cenchen Zhan、Xu-Feng Zhang、Michael E. Kort

  DOI：10.1021/acs.jmedchem.6b00063

  日期：2016.4.14

  makes it an appealing target for the potential development of new pain drugs. The utility of nonselective Nav blockers is often limited due to adverse cardiovascular and CNS side effects. We sought more selective Nav1.7 blockers with oral activity, improved selectivity, and good druglike properties. The work described herein focused on a series of 3- and 4-substituted indazoles. SAR studies of 3-substituted

  Na v 1.7电压门控离子通道在疼痛信号传导途径中的作用的遗传验证使其成为潜在的新型止痛药开发目标。由于心血管和中枢神经系统的不良反应，非选择性Na v阻滞剂的应用常常受到限制。我们寻求具有口服活性，更高的选择性和良好的药物性质的更具选择性的Na v 1.7阻滞剂。本文所述的工作集中于一系列3-和4-取代的吲唑。3取代的吲唑的SAR研究得到了类似物7，其在体外和体内的活性良好，但在大鼠体内的药代动力学却很差。对4-取代的吲唑的优化产生了两种化合物27和48，具有良好的体外和体内活性，并具有改善的大鼠药代动力学特征。27和48在急性大鼠单碘乙酸盐诱发的骨关节炎模型的疼痛中均显示出强劲的活性，而48的亚慢性给药则显示在7天内向较低的EC 50转移。
• SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES
  申请人：Kansas State University Research Foundation

  公开号：US20200306737A1

  公开（公告）日：2020-10-01

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

  手性聚乙烯吡咯烷酮（CSPVP），CSPVP与金属纳米团簇催化剂等核心物种形成的络合物，以及利用这种络合物进行对映选择氧化反应的方法被揭示。CSPVP络合物可用于不对称二醇氧化、烯烃对映选择氧化以及碳-碳键形成反应等。CSPVP还可以与蛋白质、DNA和RNA等生物分子形成络合物，并用作siRNA或dsRNA传递的纳米载体。
• Expeditious Syntheses of Sugar-Modified Nucleosides and Collections Thereof Exploiting Furan-, Pyrrole-, and Thiophene-Based Siloxy Dienes
  作者：Gloria Rassu、Franca Zanardi、Lucia Battistini、Enrico Gaetani、Giovanni Casiraghi

  DOI：10.1021/jm960400q

  日期：1997.1.1

  enriched 2',3'-dideoxynucleosides 14a-c (alpha and beta anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (alpha and beta anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (beta anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-but

  一系列单独的糖修饰的嘧啶核苷，包括对映体富集的2'，3'-二脱氧核苷14a-c（L和D系列的α和β端基异构体），2'，3'-二脱氧-4'-硫代核苷21a-合成了c（L和D系列的α和β端基异构体）和2'，3'-二脱氧-4'-氮杂核苷28a-c（L和D系列的β端基异构体）立体化学效率，利用三元组的多功能杂环甲硅烷氧基二烯，即2-（叔丁基二甲基甲硅烷氧基）呋喃（TBSOF），2-（叔丁基二甲基甲硅烷氧基）噻吩（TBSOT）和N-（叔丁氧基羰基）-2-（叔丁基二甲基甲硅烷氧基）吡咯（TBSOP）。合成方法有利地使用甘油醛丙酮化物的对映体（D-1和L-1）作为手性来源和甲酰基阳离子的合成等同物。