1-苯基-2-吡咯烷酮 | 4641-57-0

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-苯基-2-吡咯烷酮
• 中文别名: N-苯基吡咯烷酮
• 英文名称: 1-phenylpyrrolidin-2-one
• 英文别名: N-phenyl-2-pyrrolidone；N-phenyl pyrrolidone；1-phenyl-2-pyrrolidinone
• CAS: 4641-57-0
• 化学式: C₁₀H₁₁NO
• mdl: MFCD00003192
• 分子量: 161.203
• InChiKey: JMVIVASFFKKFQK-UHFFFAOYSA-N

物化性质

• 熔点：
  67-69 °C (lit.)
• 沸点：
  123 °C/0.2 mmHg (lit.)
• 密度：
  1.0840 (rough estimate)
• 闪点：
  123°C/0.2mm
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯、甲醇（少许）
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S37/39
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  3
• 海关编码：
  2933790090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

1-Phenyl-2-pyrrolidone Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1-Phenyl-2-pyrrolidone

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1-Phenyl-2-pyrrolidone
Percent: >99.0%(GC)
CAS Number: 4641-57-0
Chemical Formula: C10H11NO

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1-Phenyl-2-pyrrolidone

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
1-Phenyl-2-pyrrolidone

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Colour: White - Very pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:68°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx)
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
1-Phenyl-2-pyrrolidone

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

1-苯基-2-吡咯烷酮是一种吡咯烷酮化合物，属于重要的含氮杂环骨架。在天然产物中广泛存在，许多含有吡咯烷酮结构单元的天然产物和人工合成化合物都具有强大的生物活性和优异的发光性能，在新药和光电材料研发中发挥了重要作用。

制备

向10 mL史莱克管中依次加入N-苯基环己基胺（0.5 mmol，81 mg）、乙腈（5 mL）、无水醋酸铜（1 mmol，181 mg）、碘化钾（1 mmol，166 mg）和过硫酸氢钾复合盐（Oxone，615 mg，1 mmol），抽真空充氧气（1 atm）。之后将其置于80℃油浴中搅拌反应12小时。然后，加入10 mL饱和食盐水淬灭反应，用乙酸乙酯萃取三次（每次10 mL），合并有机相，用无水硫酸钠干燥。过滤后旋干，并通过硅胶柱分离（石油醚/乙酸乙酯＝3/1）得到白色固体产物1-苯基-2-吡咯烷酮（47 mg，58％）。

反应信息

• 作为反应物：
  描述：

  1-苯基-2-吡咯烷酮 在 dimethyl(phenyl)silyl lithium 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以25%的产率得到1-phenyl-3-(4-phenylaminobut-1-enyl)-pyrrolidin-2-one
  参考文献：
  名称：

  The reaction of phenyldimethylsilyllithium with N-phenylpyrrolidone

  摘要：

  苯基二甲基甲硅烷基锂与N-苯基吡咯烷酮5反应，生成已知的四环胺[2,3,3a,3b,4,5,6,11b-八氢-3aα,3bα,11bα-1-苯基-1H-二吡咯并(1,2a∶3′,2′c)喹啉及其3bβ异构体]6和7。

  DOI：

  10.1039/b210445h
• 作为产物：
  描述：

  N-苯基哌啶 在 亚硝酸特丁酯 、 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 、 氯化铵 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 15.0h， 生成 1-苯基-2-吡咯烷酮
  参考文献：
  名称：

  由t BuONO促进的N-芳基哌啶的C–C / C–N键的选择性切割和可调功能

  摘要：

  本文提出了在无金属条件下t BuONO促进的N-芳基哌啶中惰性CC -C / C-N键的选择性裂解和可调功能。具体而言，当反应在分子筛存在下在乙腈中进行时，形成了合成上有用的无环N-甲酰基腈。另一方面，当使用醇作为反应介质时，相应的反应通过机理上不同的途径提供了N-亚硝基链酯作为主要产物。

  DOI：

  10.1021/acs.orglett.9b00226
• 作为试剂：
  描述：

  4-叔丁基苯乙烯 、 重氮乙酸乙酯 在 1-苯基-2-吡咯烷酮 、 zinc trifluoromethanesulfonate 、 对甲苯磺酰胺 作用下， 以 环己烷 为溶剂， 反应 12.0h， 生成 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  磺酰胺酰胺酰胺的截获：Zn（OTf）2催化合成（E）-N-磺酰基am

  摘要：

  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。

  DOI：

  10.1039/c7cc07364j

文献信息

• Metal‐Free Synthesis of <i>N</i> ‐Aryl Amides using Organocatalytic Ring‐Opening Aminolysis of Lactones
  作者：Wusheng Guo、José Enrique Gómez、Luis Martínez‐Rodríguez、Nuno A. G. Bandeira、Carles Bo、Arjan W. Kleij

  DOI：10.1002/cssc.201700415

  日期：2017.5.9

  Catalytic ring‐opening of bio‐sourced non‐strained lactones with aromatic amines can offer a straightforward, 100 % atom‐economical, and sustainable pathway towards relevant N‐aryl amide scaffolds. Herein, the first general, metal‐free, and highly efficient N‐aryl amide formation is reported from poorly reactive aromatic amines and non‐strained lactones under mild operating conditions using an organic

  生物来源的非应变内酯与芳族胺的催化开环可以提供一种直接的，100％原子经济且可持续的通往相关N芳基酰胺支架的途径。在此，据报道，在温和的操作条件下，使用有机双环胍催化剂，由反应性较差的芳族胺和非应变的内酯首次形成了无金属且高效的N-芳基酰胺。该协议具有很高的应用潜力，例如与药物相关的分子的形式合成。
• Dye–polyoxometalate coordination polymer as a photo-driven electron pump for photocatalytic radical coupling reactions
  作者：Zheng Ming、Tiexin Zhang、Wenming Tian、Jianing Li、Zhenhui Liu、Renhai Liu、Zhongmin Liu、Chunying Duan

  DOI：10.1039/d1cc04209b

  日期：——

  To alleviate diffusion-limited photoinduced electron transfer (PET) in solution, a triphenylamine-derived dye and a Keggin polyoxometalate-type electron relay were coupled into a coordination polymer to photoinduce long-lived charge-separation pairs with enough reductive/oxidative potential to pump multiple electrons unidirectionally from external electron donors to acceptors, thus furnishing photocatalytic

  为了减轻溶液中扩散受限的光致电子转移 (PET)，将三苯胺衍生的染料和 Keggin 多金属氧酸盐型电子继电器耦合到配位聚合物中，以光诱导长寿命的电荷分离对，并具有足够的还原/氧化电位来泵浦多个电子单向从外部电子供体到受体，从而提供光催化自由基偶联，以提供增值的 α-氨基 C-H 芳基化产物。
• Phenyl 4-(2-oxopyrrolidin-1-yl)benzenesulfonates and phenyl 4-(2-oxopyrrolidin-1-yl)benzenesulfonamides as new antimicrotubule agents targeting the colchicine-binding site
  作者：Mathieu Gagné-Boulet、Chahrazed Bouzriba、Atziri Corin Chavez Alvarez、Sébastien Fortin

  DOI：10.1016/j.ejmech.2020.113136

  日期：2021.3

  agents designated as N-phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates (PIB–SOs) and phenyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonamides (PIB–SAs). Our previous structure-activity relationship studies (SAR) focused on the aromatic ring B of PIB-SOs and PIB-SAs leaving the impact of the phenylimidazolidin-2-one moiety (ring A) on the binding to the colchicine-binding site (C-BS) poorly studied. Therefore

  我们最近设计并制备了新的有效抗微管剂家族，命名为N4-（2-氧代咪唑啉-1-基）苯磺酸苯酯（PIB-SOs）和4-（2-氧代咪唑啉-1-基）苯磺酰胺（PIB-SAs）。我们之前的结构活性关系研究（SAR）专注于PIB-SO和PIB-SA的芳香环B，而苯基咪唑啉二-2-酮部分（环A）对秋水仙碱结合位点的结合（C -BS）学习得不好。因此，本研究的目的是评估由吡咯烷-2-酮部分取代咪唑烷-2--2-酮（IMZ）的效果。为此，设计，制备了15种新的4-（2-氧杂吡咯烷-1-基）苯磺酸苯基酯（PYB-SO）和15种苯基4-（2-氧杂吡咯烷-1-基）苯磺酸酰胺（PYB-SA）衍生物，化学表征和生物学评估。PYB-SO和PYB-SA在低纳摩尔至低微摩尔范围内显示抗增殖活性（0。在人HT-1080，HT-29，M21和MCF7癌细胞系上分别为0087–8.6μM和0.056–21μM）。而且，它们阻断了G2
• Synthesis of Lactams by Regioselective Reduction of Cyclic Dicarboximides
  作者：Maria J. Milewska、Tomasz Bytner、Tadeusz Połoński

  DOI：10.1055/s-1996-4405

  日期：1996.12

  Lactams can be obtained by the monothionation of imides with Lawesson’s reagent followed by the desulfurization of resulted monothioimides with Raney nickel.

  可以通过使用Lawesson试剂对亚酰胺进行单硫化，然后用Raney镍对生成的单硫亚酰胺进行脱硫来获得酰胺。
• Synthesis of nitrogen heterocycles <i>via</i> α-aminoalkyl radicals generated from α-silyl secondary amines under visible light irradiation
  作者：Kazunari Nakajima、Mai Kitagawa、Yuya Ashida、Yoshihiro Miyake、Yoshiaki Nishibayashi

  DOI：10.1039/c4cc03000a

  日期：——

  We have succeeded in the visible light-mediated synthetic use of α-aminoalkyl radicals derived from α-silyl secondary amines toward addition to α,β-unsaturated carbonyl compounds. The resulting γ-aminocarbonyl compounds are converted into γ-lactams and pyrroles in a one-pot process.

  我们已成功地利用可见光介导合成了从α-硅烷二级胺衍生的α-氨基烷基自由基，用于加成到α,β-不饱和羰基化合物。所得的γ-氨基羰基化合物在一个锅过程中转化为γ-内酰胺和吡咯烷。

表征谱图