1,5-二氢-2-吡咯酮 | 4031-15-6

• 物质功能分类: 医药中间体
• 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: 1,5-二氢-2-吡咯酮
• 中文别名: 3-吡咯啉-2-酮；1H-吡咯-2(5H)-酮
• 英文名称: 3-pyrrolin-2-one
• 英文别名: Δ³-Pyrrolin-2-on；1H-pyrrol-2(5H)-one；1,5-Dihydro-2H-pyrrol-2-on；Δ³-pyrrolin-2-one；1,5-dihydro-2H-pyrrol-2-one；3-Pyrrolin-2-on；1,5-Dihydro-pyrrol-2-one；1,2-dihydropyrrol-5-one
• CAS: 4031-15-6
• 化学式: C₄H₅NO
• mdl: MFCD06658513
• 分子量: 83.0898
• InChiKey: CDCHBOQVXIGZHA-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  292.2±23.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)
• 溶解度：
  易溶于可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H227,H315,H319,H335
• 储存条件：
  -20°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1H-pyrrol-2(5H)-one
Synonyms: 1,5-Dihydro-pyrrol-2-one;

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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: 1H-pyrrol-2(5H)-one
CAS number: 4031-15-6

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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: C4H5NO
Molecular weight: 83.1

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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：

  1,5-二氢-2-吡咯酮 生成 cyclopyrrolone
  参考文献：
  名称：

  GAVINA, FRANCISCO;COSTERO, ANA M.;ANDREU, M. ROSARIO;LUIS, SANTIAGO V., J. ORG. CHEM., 53,(1988) N6, C. 6112-6113

  摘要：

  DOI：
• 作为产物：
  描述：

  马来酰亚胺 在 三氟甲磺酸 、 环己烷 、 五氟化锑 作用下， 反应 0.17h， 以100%的产率得到1,5-二氢-2-吡咯酮
  参考文献：
  名称：

  马来酰亚胺和邻苯二甲酰亚胺的超酸活化及其与环己烷和芳烃的反应

  摘要：

  当在 CF3SO3H/SbF5 酸体系中活化时，马来酰亚胺 (1) 和邻苯二甲酰亚胺 (2) 与环己烷进行选择性离子氢化，分别得到 1,5-二氢吡咯-2-酮 (3) 和邻苯二甲酰亚胺 (11)。当用卤化铝处理时，N-苯基马来酰亚胺 (4) 与环己烷反应生成 N-苯基琥珀酰亚胺 (5)，而 2 仍然生成 11。酰亚胺 1 也在三氟甲磺酸 (CF3SO3H) 中与苯缩合生成 1,5-二氢- 5,5-diphenylpyrrol-2-one (7) 作为主要产品。然而，在卤化铝存在下，1 与苯、甲苯和邻二氯苯反应，分别生成 3-芳基琥珀酰亚胺 8-10。在三氟甲磺酸和卤化铝的作用下，酰亚胺 2 与苯反应生成 3,3-二苯基邻苯二甲酰亚胺 (12)。这些反应的机理，讨论了超亲电双阳离子中间体的潜在参与。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  DOI：

  10.1002/ejoc.200600486

文献信息

• Synthetic Strategies for the Synthesis and Transformation of Substituted Pyrrolinones as Advanced Intermediates for Rhazinilam Analogues
  作者：Inga Kholod、Olivier Vallat、Ana-Maria Buciumas、Antonia Neels、Reinhard Neier

  DOI：10.1002/ejoc.201402903

  日期：2014.12

  The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction

  具有固定二面角的 rhazinilam 的联芳核心结构是其独特的体外细胞毒活性的关键因素。大多数相关的天然产物是氧化形式的 rhazinilam。用吡咯啉酮环代替敏感的吡咯环是我们对罗嗪类似物的初步策略的基础。为了这个目标，研究了与向山羟醛反应和施陶丁格反应交叉的序列变体。将适当取代的苯乙酮与 O-甲基 O-三甲基甲硅烷基乙烯酮缩醛反应以良好至极好的产率得到吡咯啉酮 8a 和 8b。这些中间体可以通过四个高产率步骤转化为吡咯前体 7a-c，其中包含构建 rhazinilam 环 A、B 和 C 所需的所有原子。我们的研究表明这些中间体缺乏稳定性。描述了针对该中心联芳基核结构的替代合成方法。
• Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H ₂ O ₂ in Polar Solvents
  作者：Natalia Llopis、Patricia Gisbert、Alejandro Baeza

  DOI：10.1002/adsc.202100214

  日期：2021.7

  The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans

  已经描述了涉及使用 H 2 O 2或过氧化氢尿素与极性溶剂的吲哚的氧化裂解（Witkop 氧化）。在这些溶剂中，1,1,1,3,3,3-六氟异丙醇 (HFIP) 脱颖而出，通常以更高的产率提供相应的 2-酮乙酰苯胺。所描述的协议还能够氧化不同的吡咯和呋喃衍生物。此外，该程序是大规模实施的，从反应混合物中蒸馏出 HFIP 并重复使用（最多 4 个循环），而不会显着损害反应结果，这说明了其可持续性和适用性。
• Highly Enantioselective Copper-Phosphoramidite-Catalyzed Conjugate Addition of Dialkylzinc Reagents to Acyclic α,β-Unsaturated Imides
  作者：Mauro Pineschi、Federica Del Moro、Valeria Di Bussolo、Franco Macchia

  DOI：10.1002/adsc.200505309

  日期：2006.2

  the β-position of aliphatic carboxylic acid derivatives with high enantioselectivities by the use of a commercially available chiral ligand is reported. N-Acylpyrrolidinones, as simple derivatives of an α,β-unsaturated carboxylic acid, were found to be the substrates of choice featuring good reactivity and high enantioselectivities (up to >99% ee).

  报道了通过使用可商购的手性配体以高对映选择性将烷基片段引入脂族羧酸衍生物的β-位的新的实用方法。已发现作为α，β-不饱和羧酸的简单衍生物的N-酰基吡咯烷酮是具有良好反应性和高对映选择性（高达> 99％ee）的选择底物。
• Senolytic activity of piperlongumine analogues: Synthesis and biological evaluation
  作者：Xingui Liu、Yingying Wang、Xuan Zhang、Zhengya Gao、Suping Zhang、Peizhong Shi、Xin Zhang、Lin Song、Howard Hendrickson、Daohong Zhou、Guangrong Zheng

  DOI：10.1016/j.bmc.2018.06.013

  日期：2018.8

  olefin with an exocyclic methylene at C2 render PL analogues 47–49 with increased senolytic activity. These α-methylene containing analogues are also more potent than PL in inducing ROS production in WI-38 SCs. Similar to PL, 47–49 reduce the protein levels of oxidation resistance 1 (OXR1), an important oxidative stress response protein that regulates the expression of a variety of antioxidant enzymes

  选择性清除衰老细胞（SCs）已成为治疗与年龄有关的疾病以及化学疗法和放射疗法引起的不良反应的潜在方法。通过基于细胞的表型筛选方法，我们最近确定了膳食中的天然产物哌隆定（PL）作为一种新型的抗衰老剂，是指可以选择性杀灭正常细胞或非衰老细胞的SC的小分子。为了建立PL类似物的结构-衰老活性关系，我们对PL的三甲氧基苯基和α，β-不饱和δ-戊内酰胺环进行了一系列结构修饰。我们表明三甲氧基苯基环上的修饰是很好的耐受性，而内酰胺环上的迈克尔受体对于senolytic活动至关重要。47 - 49具有增加的senolytic活性。这些含α-亚甲基的类似物在诱导WI-38 SC中产生ROS方面也比PL更有效。与PL相似，47 – 49降低了抗氧化蛋白1（OXR1）的蛋白水平，OXR1是一种重要的氧化应激反应蛋白，可调节细胞中多种抗氧化酶的表达。这项研究为发现用于治疗用途的镇静剂提供了有用的起点。
• Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization
  作者：Ming Chen、Guangbin Dong

  DOI：10.1021/jacs.7b04722

  日期：2017.6.14

  N-protected lactams to their conjugated unsaturated counterparts under mildly acidic conditions. The reaction is consistently operated at room temperature and tolerates a wide range of functional groups, showing reactivity complementary to that of prior desaturation methods. Lactams with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility of this method

  描述了一种直接催化方法，用于N的α，β-去饱和-保护的内酰胺在弱酸性条件下与其共轭的不饱和对应物。该反应在室温下持续进行，并能耐受各种官能团，显示出与现有的去饱和方法互补的反应性。具有不同环尺寸和在不同位置的取代基的内酰胺均反应顺利。该方法的合成效用已在Rolipram的简明合成中得到了证明。另外，线性酰胺也被证明是有效的底物，并且邻苯二甲酰基保护的产物用作获得各种共轭羧酸衍生物的方便前体。这种去饱和方法避免了强碱的存在，关键是将软化烯醇化与Pd催化的氧化过程相结合。

表征谱图