3-苯胺基-2-环己烯-1-酮 | 24706-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苯胺基-2-环己烯-1-酮
• 中文别名: 3-(苯基氨基)环己-2-烯-1-酮；3-苯胺基环己基-2-烯-1-酮
• 英文名称: 3-phenylaminocyclohex-2-enone
• 英文别名: 3-(phenylamino)-2-cyclohexen-1-one；3-anilinocyclohex-2-en-1-one；2-Cyclohexen-1-one, 3-(phenylamino)-
• CAS: 24706-50-1
• 化学式: C₁₂H₁₃NO
• mdl: MFCD00082654
• 分子量: 187.241
• InChiKey: IVONJXTZXFTWNA-UHFFFAOYSA-N

物化性质

• 熔点：
  178-182 °C
• 沸点：
  324.9±42.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规定使用和储存，则不会分解，请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• RTECS号：
  GW7600000
• 海关编码：
  2922399090
• 储存条件：
  保持贮藏器密封，并将其放入一个紧密封装的容器中。应储存在阴凉、干燥的地方。

SDS

Name:	3-(Phenylamino)cyclohex-2-ene-1-one 98% Material Safety Data Sheet
Synonym:
CAS:	24706-50-1

Section 1 - Chemical Product MSDS Name:3-(Phenylamino)cyclohex-2-ene-1-one 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24706-50-1	3-(Phenylamino)cyclohex-2-ene-1-one	98%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 24706-50-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: yellow-green - fine
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 178 - 182 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C12H13NO
Molecular Weight: 187.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24706-50-1: GW7600000 LD50/LC50:
Not available.
Carcinogenicity:
3-(Phenylamino)cyclohex-2-ene-1-one - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 24706-50-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24706-50-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24706-50-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-苯胺基-2-环己烯-1-酮 在 盐酸 、 水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 2-(2-(4-methoxyphenyl)-4-oxo-1-phenyl-4,5,6,7-tetrahydro-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  通过多米诺缩合、热环化和芳构化从芳基乙二醛和烯胺中取代苯并[a]咔唑和吲哚乙酸

  摘要：

  已经开发了一种两步法，其中环己酮稠合的 2-(3-吡咯基)-2-氰基乙酰胺，烯胺、芳基乙二醛和丙二腈的缩合产物，通过一个-分步热环化和钯催化芳构化。生物学上重要的吲哚乙酸衍生物也可以从相同的氰基乙酰胺的水解和芳构化中以良好的产率获得。

  DOI：

  10.1002/ejoc.201402085
• 作为产物：
  描述：

  1,3-环己二酮 在 苯胺 作用下， 以94%的产率得到3-苯胺基-2-环己烯-1-酮
  参考文献：
  名称：

  Enaminones as potential prodrugs of primary and secondary amines

  摘要：

  本发明揭示了一种新型的酶降解性易制备的烯酮衍生物，可作为一次性和二次性胺的潜在前药。此外，还揭示了包含上述胺的组合物及将该组合物用于温血动物的给药方法。

  公开号：

  EP0214009A3

文献信息

• Cyclization of Cyanoethylated Ketones as a Route to 6-Substituted Indole Derivatives
  作者：Jan Bergman、Birgitta Stensland

  DOI：10.1002/jhet.2048

  日期：2014.1

  δ‐Cyanoketones are quickly cyclized with KOtBu to 3‐aminocyclohex‐2‐enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3‐amino‐6,6‐dimethylcyclohex‐2‐enone gave 3‐chloro‐6,6‐dimethyl‐2,5,6,7‐tetrahydroindole‐2,5‐dione, whose structure was corroborated by X‐ray crystallography, whereas the corresponding molecule without the blocking gem‐dimethyl groups

  δ-氰基酮可通过KOtBu快速环化成3-氨基环己-2-烯酮衍生物，当用草酰氯处理时，它们会生成取代的吲哚。因此，3-氨基-6,6-二甲基环己-2-烯酮产生了3-氯-6,6-二甲基-2,5,6,7-四氢吲哚-2,5-二酮，其结构得到了X射线的证实。晶体学，而没有封闭的二甲基-二甲基基团的相应分子3-氨基环己-2-烯酮通过氢转移得到6-氯-3-羟基羟吲哚。
• An Efficient Strategy for the Synthesis of Naphtho[2,3-b][1,6]naphthyridines Promoted by Acetic Acid
  作者：Furen Zhang、Zhenlu Shen、Chunmei Li

  DOI：10.1055/a-1479-4420

  日期：2021.7

  A three-component domino reaction for the synthesis of naphtho[2,3-b][1,6]naphthyridine derivatives has been established. Such strategy exhibited excellent substrate scope including various enaminones and aldehydes that afforded a series of multifunctionalized naphtho[2,3-b][1,6]naphthyridine derivatives with 70–86% yields. The advantages of bond-forming efficiency, accessibility of starting materials

  已经建立了用于合成萘并[2,3-b] [1,6]萘啶衍生物的三组分多米诺反应。这种策略显示出优异的底物范围，包括各种烯胺酮和醛，可提供一系列多官能化的萘并[2,3-b] [1,6]萘啶衍生物，产率为70-86％。形成键的效率，起始原料的可及性以及作为唯一副产物的水的优势为生物1,6-萘啶提供了无价的获取途径。
• Efficient Synthesis of Functionalized Dihydro-1<i>H</i>-indol-4(5<i>H</i>)-ones via One-Pot Three-Component Reaction under Catalyst-Free Conditions
  作者：Hui-Yan Wang、Da-Qing Shi

  DOI：10.1021/co4000198

  日期：2013.5.13

  A facile and efficient one-pot procedure for the preparation of functionalized dihydro-1H-indol-4(5H)-ones by a catalyst-free, three-component reaction of 1,3-dicarbonyl compounds, arylglyoxal monohydrate and enaminones under mild conditions in excellent yield is reported. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional purifications

  一种简便有效的一锅法，用于在温和条件下通过无催化剂的1,3-二羰基化合物，芳基乙二醛一水合物和烯胺酮的三组分反应制备官能化的二氢-1H-吲哚-4（5H）-酮据报道，其收率极高。证实该合成遵循组辅助纯化（GAP）化学过程，该过程可避免传统的纯化，色谱法和重结晶。
• Monobromomalononitrile: an efficient regioselective mono brominating agent towards active methylene compounds and enamines under mild conditions
  作者：Sudipta Pathak、Ashis Kundu、Animesh Pramanik

  DOI：10.1039/c3ra46687f

  日期：——

  The potential of monobromomalononitrile (MBM) as a convenient source of cationic bromine in organic bromination reaction has been explored. Studies reveal that MBM can be a good substitute for N-bromosuccinimide (NBS) in various respects. Enamines and active methylene compounds bearing aromatic rings are selectively mono brominated on the vinylic and active methylene group respectively on reaction

  已经探索了单溴丙二腈（MBM）作为有机溴化反应中阳离子溴的方便来源的潜力。研究表明，MBM可以很好地替代N-溴代琥珀酰亚胺（NBS）的各个方面。与MBM反应时，带有芳香环的烯胺和活性亚甲基化合物分别在乙烯基和活性亚甲基上选择性地单溴化。该方法的优点是易于制备MBM，反应时间短和产物形成的产率高。此外，它提供了无金属的绿色溴化剂，它对制药业更方便。即使在加入过量的MBM之后，单溴化反应也仅在活性亚甲基上发生。包含吸电子，给电子和邻位取代的胺的胺反应平稳，仅以良好的收率得到乙烯基单溴产物，而没有产生任何副产物。
• Synthesis of fused-tetrahydropyrimidines: one-pot methylenation–cyclization utilizing two molecules of CO₂
  作者：Yulei Zhao、Xuqiang Guo、Yulan Du、Xinrui Shi、Shina Yan、Yunlin Liu、Jinmao You

  DOI：10.1039/d0ob01504k

  日期：——

  A methylenation–cyclization reaction, employing cyclic enaminones with primary aromatic amines and two molecules of CO2, furnishing fused-tetrahydropyrimidines, is discussed. In this Cs2CO3 and ZnI2 catalyzed one-pot two-step procedure, two molecules of CO2 were selectively converted to methylene groups. The multi-component reaction might proceed through the formation of bis(silyl)acetal which was

  讨论了使用环状烯胺酮与伯芳香胺和两个 CO 2分子，提供稠合四氢嘧啶的亚甲基化-环化反应。在这个Cs 2 CO 3和ZnI 2催化的一锅两步法中，两个CO 2分子被选择性地转化为亚甲基。多组分反应可能通过形成双（甲硅烷基）缩醛进行，然后是缩合和进一步的氮杂-狄尔斯-阿尔德反应。氢喹唑啉、氢环戊二烯[ d ]嘧啶和氢茚并[1,2- d ]嘧啶衍生物可以以CO 2作为C1源有效地制备。

表征谱图