1-(3-氯苯基)-2-哌啶酮 | 132573-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(3-氯苯基)-2-哌啶酮
• 英文名称: 1-(3-chloro-phenyl)-piperidin-2-one
• 英文别名: 1-(3-chlorophenyl)-2-piperidone；1-(3-Chlorophenyl)piperidin-2-one
• CAS: 132573-12-7
• 化学式: C₁₁H₁₂ClNO
• mdl: MFCD04037085
• 分子量: 209.675
• InChiKey: QMCIOETXUFJTAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(3-Chlorophenyl)piperidin-2-one
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: 1-(3-Chlorophenyl)piperidin-2-one
CAS number: 132573-12-7

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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: C11H12ClNO
Molecular weight: 209.7

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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, hydrogen chloride.

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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-(3-氯苯基)-2-哌啶酮 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 5-(3-Chloro-phenylamino)-pentanoic acid anion
  参考文献：
  名称：

  碱性溶液中羰基化合物的反应。第14部分。碱性水解取代的N-甲基甲酰苯胺，N-甲基乙酰苯胺，1-苯基氮杂环丁烷-2-酮，1-苯基-2-吡咯烷酮和1-苯基-2-哌啶酮

  摘要：

  一系列取代的1-苯基氮杂环丁烷-2-酮，-2-吡咯烷酮和-2-哌啶酮以及N-甲基乙酰苯胺和N的碱水解速率系数已经在几个温度下测量了在二甲基亚砜水溶液和在二恶烷或水中的α-甲基甲酰苯胺。该反应在底物中是一阶的，对于内酰胺和乙酰苯胺而言，该反应是在碱中的一阶，对于甲酰苯胺，在碱中是一阶和二阶。已对每个系统评估了Hammett反应常数和活化参数。已经检查了相对反应性，盐，溶剂和溶剂同位素效应。建议了以下反应机理。对于β-内酰胺，途径似乎是氢氧化物的速率决定性攻击，而对于γ-和δ-内酰胺和乙酰苯胺而言，碳-氮键的速率决定裂变是在碱的平衡添加之后发生的。通过确定水催化或碱催化的速率。

  DOI：

  10.1039/p29900002103
• 作为产物：
  描述：

  哌啶酮 、 1-氯-3-碘苯 在 copper(I) oxide 、 potassium phosphate 、 四丙基溴化铵 作用下， 以 水 为溶剂， 反应 24.0h， 以63%的产率得到1-(3-氯苯基)-2-哌啶酮
  参考文献：
  名称：

  水中酰胺与芳基卤化物的高效无配位铜催化N-芳基化

  摘要：

  已经开发了一种方便有效的方案，用于在水中使用无配位体的氧化铜（I）催化剂将酰胺和芳基碘化物交叉偶联。各种酰胺衍生物以中等至良好的产率（高达88％）提供了相应的N-芳基化产物。

  DOI：

  10.1016/j.tetlet.2011.01.003

文献信息

• Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions
  作者：Bin Li、Mingli Hu、Jun Ge、Wei Xu、Jinghan Wu、Yao Tong、Zhengyi Zhao、Xiuxiu Liu、Ling He

  DOI：10.1039/d3ob00150d

  日期：——

  The reactions of direct Csp2–H chalcogenylation and halogenation of N-arylpyrrolidone under the action of PIFA without a directing group and under metal-free conditions were reported in this paper. Diphenyl selenide/sulfur and selenium phenyl halides were used as reaction reagents to obtain chalcogenylated and halogenated N-arylpyrrolidone products, respectively. The mechanistic studies indicated that

  本文报道了在无导向基团和无金属条件下，PIFA作用下N-芳基吡咯烷酮的直接Csp 2 -H硫属基化和卤化反应。二苯基硒化物/硫和硒苯基卤化物用作反应试剂，分别得到硫属化和卤化的N-芳基吡咯烷酮产物。机理研究表明，这些反应可能涉及自由基途径。初步抗肿瘤试验表明，这些化合物在体外对人急性白血病细胞K562具有中强活性，可作为后续研究的先导化合物。
• Reactions of carbonyl compounds in basic solutions. Part 14. The alkaline hydrolysis of substituted N-methylformanilides, N-methylacetanilides, 1-phenylazetidin-2-ones, 1-phenyl-2-pyrrolidones, and 1-phenyl-2-piperidones
  作者：Keith Bowden、Keith Bromley

  DOI：10.1039/p29900002103

  日期：——

  in aqueous dimethyl sulphoxide and in aqueous dioxane or water have been measured at several temperatures. The reactions were first order in substrate and, for the lactams and acetanilides, first order in base and, for the formanilides, both first and second order in base. Hammett reaction constants and activation parameters have been evaluated for each system. The relative reactivity, salt, solvent

  一系列取代的1-苯基氮杂环丁烷-2-酮，-2-吡咯烷酮和-2-哌啶酮以及N-甲基乙酰苯胺和N的碱水解速率系数已经在几个温度下测量了在二甲基亚砜水溶液和在二恶烷或水中的α-甲基甲酰苯胺。该反应在底物中是一阶的，对于内酰胺和乙酰苯胺而言，该反应是在碱中的一阶，对于甲酰苯胺，在碱中是一阶和二阶。已对每个系统评估了Hammett反应常数和活化参数。已经检查了相对反应性，盐，溶剂和溶剂同位素效应。建议了以下反应机理。对于β-内酰胺，途径似乎是氢氧化物的速率决定性攻击，而对于γ-和δ-内酰胺和乙酰苯胺而言，碳-氮键的速率决定裂变是在碱的平衡添加之后发生的。通过确定水催化或碱催化的速率。
• Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water
  作者：Fui-Fong Yong、Yong-Chua Teo、Guan-Leong Chua、Gina Shiyun Lim、Yizhen Lin

  DOI：10.1016/j.tetlet.2011.01.003

  日期：2011.3

  A convenient and efficient protocol has been developed for the cross-coupling of amides and aryl iodides using a ligand-free copper(I) oxide catalyst in water. A variety of amide derivatives afforded the corresponding N-arylated products in moderate to good yields (up to 88%).

  已经开发了一种方便有效的方案，用于在水中使用无配位体的氧化铜（I）催化剂将酰胺和芳基碘化物交叉偶联。各种酰胺衍生物以中等至良好的产率（高达88％）提供了相应的N-芳基化产物。