N-(2-乙酰苯基)乙酰胺 | 5234-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-(2-乙酰苯基)乙酰胺
• 中文别名: 3-(N-乙酰基氨基)苯乙酮
• 英文名称: N-(2-acetylphenyl)acetamide
• 英文别名: o-acetylaminoacetophenone；2'-acetamidoacetophenone；N-[2-(1-oxo-1-ethanyl)phenyl]acetamide
• CAS: 5234-26-4
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD00032277
• 分子量: 177.203
• InChiKey: YSZGCNKBKQQPAH-UHFFFAOYSA-N

物化性质

• 熔点：
  77 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  367.4±25.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332
• 储存条件：
  室温密封，干燥保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-(2-Acetyl-phenyl)-acetamide
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: N-(2-Acetyl-phenyl)-acetamide
CAS number: 5234-26-4

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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: C10H11NO2
Molecular weight: 177.2

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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：

  N-(2-乙酰苯基)乙酰胺 在 ammonium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 10.0h， 生成 2,4-二甲基喹唑啉
  参考文献：
  名称：

  Pd(0)-catalyzed benzylic arylation–oxidation of 4-methylquinazolines via sp3 C–H activation under air conditions

  摘要：

  报道了一种高效且选择性的Pd(0)催化的4-甲基喹唑啉sp³ C–H键芳基化–氧化方法。该方法能够在4-甲基喹唑啉的苄位引入芳基酮，无需额外的诱导基团，并且使用大气中的氧作为唯一的氧化剂。

  DOI：

  10.1039/c3ob41488d
• 作为产物：
  描述：

  邻硝基苯乙酮 在 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 N-(2-乙酰苯基)乙酰胺
  参考文献：
  名称：

  2-芳基-2,3-二氢-4(1H)-喹啉酮缩氨基脲类 化合物及其应用

  摘要：

  本发明涉及医药技术领域，设计并合成了一系列结构新颖的2‑芳基‑2,3‑二氢‑4(1H)‑喹啉酮缩氨基脲类衍生物(I)及其在药学上可接受的盐、溶剂化物、光学异构体或多晶型物。所述的衍生物(I)及其在药学上可接受的盐、溶剂化物、光学异构体或多晶型物可以作为活性成分与药学上可接受的载体混合制备成药物组合物。本发明通过对所述衍生物(I)及其在药学上可接受的盐、溶剂化物、光学异构体或多晶型物的抗真菌活性采用二倍浓度稀释法进行了测试，结果表明，所述的衍生物对临床上常见的致病真菌有较强的杀灭作用，并有望克服目前临床上广泛使用的唑类抗真菌药的毒副作用大、易产生耐药性等缺陷。

  公开号：

  CN108558756B

文献信息

• 1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis
  作者：Prasath Kothandaraman、Bing Qin Koh、Taweetham Limpanuparb、Hajime Hirao、Philip Wai Hong Chan

  DOI：10.1002/chem.201202606

  日期：2013.2.4

  on NIS (N‐iodosuccinimide)‐mediated cycloisomerization reactions of 1‐(2′‐anilinyl)prop‐2‐yn‐1‐ols to gem‐3‐(diiodomethyl)indolin‐2‐ones and 2‐(iodomethylene)indolin‐3‐ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3‐ and 2‐oxindole products, respectively. In the case of the latter, the transformation features

  依赖于NIS（A合成方法Ñ碘代丁二酰亚胺）丙-2-炔-1-醇向1-（2'-苯胺基） -介导的反应环异构宝石-3-（二碘甲基）二氢吲哚-2-酮和2- （碘亚甲基）吲哚-3-酮已被开发出来。反应被证明是化学选择性的，仲和叔醇底物分别专门提供3-和2-氧吲哚产物。对于后者，该转换具有前所未有的双重1,2-OH和1,2-烷基迁移中继。基于拟议的碘氨基环化物质的密度泛函理论（DFT）计算提供了对产物选择性这一独特差异的见解。
• Efficient synthesis of functionalized dihydroquinolines, quinolines and dihydrobenzo[b]azepine via an iron(<scp>iii</scp>) chloride-catalyzed intramolecular alkyne–carbonyl metathesis of alkyne tethered 2-amino benzaldehyde/acetophenone derivatives
  作者：Swapnadeep Jalal、Krishnendu Bera、Soumen Sarkar、Kartick Paul、Umasish Jana

  DOI：10.1039/c3ob42292e

  日期：——

  developed an efficient synthesis of 1,2-dihydroquinoline and dihydrobenzo[b]azepine derivatives involving the iron(III) chloride intramolecular alkyne–carbonyl metathesis reaction for the first time. Various functionalized 1,2-dihydroquinolines and dihydrobenzo[b]azepines were prepared from easily accessible substrates in the presence of environmentally friendly and inexpensive iron(III) chloride (10 mol%)

  在这项研究中，我们首次开发了一种有效的合成1,2-二氢喹啉和二氢苯并[ b ]氮杂衍生物的方法，该方法涉及氯化铁（III）的分子内炔烃-羰基复分解反应。在环境友好且廉价的氯化铁（III）（10 mol％）的存在下，在温和的条件下，由易于获得的底物制备了各种官能化的1,2-二氢喹啉和二氢苯并[ b ]氮杂s 。该方法适用于范围广泛的包含不同官能团的基材，并以高至优异的产率提供了装饰产品。该方法进一步扩展到一个一锅法合成的3-酰基喹啉通过通过添加NaOH / EtOH ，N-炔丙基-2-氨基苯甲醛/苯乙酮衍生物进行炔烃-羰基复分解/脱甲苯基化/芳构化。尽管对许多路易斯酸和布朗斯台德酸催化剂进行了研究，但无水氯化铁（III）却是该转化的最佳催化剂。
• Palladium-Catalyzed Direct Alkynylation of C−H Bonds in Benzenes
  作者：Mamoru Tobisu、Yusuke Ano、Naoto Chatani

  DOI：10.1021/ol901049r

  日期：2009.8.6

  Palladium-catalyzed ortho-alkynylation of aromatic C−H bonds in anilides is described. Preliminary mechanistic studies reveal that electrophilic palladation is involved. Synthetic elaborations of alkynylated products are also demonstrated.

  描述了钯催化苯甲酸酯中芳族CH键的邻位炔基化反应。初步的机理研究表明，涉及到亲电性pal裂。还展示了炔基化产物的合成精制。
• Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(<i>o</i>-acetamidophenyl)propargyl alcohols
  作者：Gadi Ranjith Kumar、Yalla Kiran Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.3762/bjoc.10.125

  日期：——

  The copper-catalyzed ketenimine formation reaction of 1-(o-acetamidophenyl)propargyl alcohols with various sulfonyl azides is found to undergo a concomitant intramolecular nucleophile attack to generate 1,2-dihydro-2-iminoquinolines after aromatization (via elimination of acetyl and hydroxy groups) and tautomerization. The reaction produces 4-substituted and 3,4-unsubstituted title compounds in moderate to good yields under mild reaction conditions.

  铜催化的1-(o-乙酰氨基苯基)丙炔醇与各种磺酰叠氮化合物的生成反应被发现会经历共同的分子内亲核攻击，生成1,2-二氢-2-亚胺喹啉，经芳香化（通过乙酰和羟基的消除）和互变异构。在温和的反应条件下，该反应以中等至良好的产率产生4-取代和3,4-未取代的产物。
• [EN] PRODUCTION OF N-ALKYLAMIDE COMPOUNDS<br/>[FR] PRODUCTION DE COMPOSES DE N-ALKYLAMIDE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2004087637A1

  公开（公告）日：2004-10-14

  The present invention provides an efficient process for the production of N-acylaniline derivatives by selectively alkylating an amide group at the nitrogen atom. The process comprises reacting an amide compound of the formula (2): (wherein, R1 and R2 are each independently an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an aryl group or a substituted aryl group) with a sulfuric acid ester in the presence of a solid metal hydroxide to give an N-alkylamide compound of the formula (3): (wherein R3 is an alkyl group and R1 and R2 have each the same meaning as described above).

  本发明提供了一种通过选择性地烷基化氮原子上的酰胺基团来生产N-酰苯胺衍生物的高效过程。该过程包括在固体金属羟基的存在下，将式（2）的酰胺化合物（其中，R1和R2分别独立地是烷基、取代烷基、烯基、取代烯基、芳基或取代芳基）与硫酸酯反应，得到式（3）的N-烷基酰胺化合物（其中R3是烷基，R1和R2的含义与上述相同）。

表征谱图