1-phenyl-3-dimethylaminoprop-2-enone | 1201-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-3-dimethylaminoprop-2-enone
• 英文别名: 3-(dimethylamino)-1-phenylprop-2-en-1-one；3-(dimethylamino)-1-phenyl-2-propen-1-one；3-(dimethylamino)-1-phenyl-propenone；3-(dimethylamino)-1-phenylprop-2-enone
• CAS: 1201-93-0
• 化学式: C₁₁H₁₃NO
• mdl: MFCD00121193
• 分子量: 175.23
• InChiKey: HUTKDPINCSJXAA-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93°C
• 沸点：
  260.0±32.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇
• 最大波长(λmax)：
  325nm(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (E)-3-(dimethylamino)-1-phenylprop-2-en-1-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: (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one
CAS number: 1201-93-0

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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: C11H13NO
Molecular weight: 175.2

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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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-Morpholinoacrylophenon	14677-24-8	C13H15NO2	217.268
  ——	Benzoyl acetaldehyde	3506-51-2	C9H8O2	148.161
  ——	1-benzoyl-2-chloroethene	3306-07-8	C9H7ClO	166.607
  苯乙酮	acetophenone	98-86-2	C8H8O	120.151

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2-methylamino-vinyl) phenyl ketone	56570-44-6	C10H11NO	161.203
  ——	1-Methylamino-3-phenyl-propen-(1)-on-(3)	877-50-9	C10H11NO	161.203
  ——	(Z)-3-(ethylamino)-1-phenylprop-2-en-1-one	34041-00-4	C11H13NO	175.23
  ——	3-(diethylamino)-1-phenylprop-2-en-1-one	3506-54-5	C13H17NO	203.284
  ——	(Z)-3-Amino-1-phenyl-propenone	23652-89-3	C9H9NO	147.177
  ——	1-phenyl-3-(pyrrolidin-1-yl)prop-2-en-1-one	3506-53-4	C13H15NO	201.268
  ——	1-Benzoyl-2-benzylamino-aethylen	14376-90-0	C16H15NO	237.301
  ——	(Z)-3-(benzylamino)-1-phenylprop-2-en-1-one	56570-47-9	C16H15NO	237.301
  ——	3-Morpholinoacrylophenon	14677-24-8	C13H15NO2	217.268
  ——	1-oxo-1-phenyl-3-(4-fluorophenyl)methylamino-2-propene	——	C16H14FNO	255.292

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-dimethylaminoprop-2-enone 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 以89%的产率得到苯甲酰乙腈
  参考文献：
  名称：

  Synthesis of 5-Substituted 3-Amino-1H-Pyrazole-4-Carbonitriles as Precursors for Microwave Assisted Regiospecific Syntheses of Pyrazolo[1,5-a]Pyrimidines

  摘要：

  描述了一条简单的合成路线，用于制备标题化合物的前体3-oxoalkanonitrile 5。将enaminones 2与盐酸羟胺在乙醇中反应，生成了aldoximes 3，这些化合物可以在碱性条件下轻易转化为5。这种方法成功应用于多种底物，产生了优良的产率。将5与三氯乙腈反应，得到3-amino-2-aroyl-4,4,4-trichloro-2-butenenitriles 6，进而与肼反应生成3-amino-1H-pyrazole-4-carbonitrile衍生物8。通过与不对称双电电荷体的区位选择性缩合反应，合成了取代的pyrazolo[1,5-a]pyridimidines。根据1H-NMR和1H-15N HMBC测定推导出所获得化合物的结构。

  DOI：

  10.3390/molecules14010078
• 作为产物：
  描述：

  1-benzoyl-2-chloroethene 在 水 作用下， 以 乙醚 为溶剂， 生成 1-phenyl-3-dimethylaminoprop-2-enone
  参考文献：
  名称：

  Reactions of (2-acylvinyl)trialkylammonium salts with nucleophilic reagents

  摘要：

  DOI：

  10.1007/bf00848707
• 作为试剂：
  描述：

  1,1-二苯乙烯 、 亚磷酸二乙酯 在 1-phenyl-3-dimethylaminoprop-2-enone 、 manganese triacetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以31%的产率得到diethyl (2,2-diphenylvinyl)phosphonate
  参考文献：
  名称：

  Mn（OAc）3-通过C sp 2 -C sp 2和P-H键裂解促进氧化C sp 3 -P键形成：获得β-酮膦酸酯

  摘要：

  Mn（OAc）3促进N，N-二甲基亚氨基酮与H-膦酸酯的氧化膦酰化作用，涉及化学和区域选择性C sp 2 –C sp 2键断裂和C sp 3 –P键形成的一步，成功提供在温和的反应条件下官能化的β-酮膦酸酯。通过C sp 3氧化C sp 3 –H / P–H交叉偶联反应初步进行了-C（C═O）键的裂解和机理研究，并提出了可能的机理。这种新颖的方法以良好的收率获得了良好的收率，显示出操作简便性，广泛的底物范围和大规模的制备方法。

  DOI：

  10.1021/acs.joc.7b02391

文献信息

• 6-N-Linked Heterocycle-Substituted 2,3,4,5-Tetrahydro-1H-Benzo[d]Azepines as 5-Ht2c Receptor Agonists
  申请人：Briner Karin

  公开号：US20080214520A1

  公开（公告）日：2008-09-04

  The present invention provides 6-substituted 2,3,4,5-tetrahydro-1H-benzo[d]azepines of Formula I as selective 5-HT 2C receptor agonists for the treatment of 5-HT 2C associated disorders including obesity, obsessive/compulsive disorder, depression, and anxiety: Formula (I) where: R 6 is selected from the group consisting of (a, b, c, d, e) and other substituents are as defined in the specification.

  本发明提供了Formula I的6-取代的2,3,4,5-四氢-1H-苯并[d]氮杂环庚烯作为选择性5-HT2C受体激动剂，用于治疗与5-HT2C相关的疾病，包括肥胖症、强迫症、抑郁症和焦虑症：Formula (I)其中：R6选自(a、b、c、d、e)等基团组成的群，其他取代基如规范中定义。
• [3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles
  作者：Ilya V. Efimov、Maria D. Matveeva、Rafael Luque、Vasiliy A. Bakulev、Leonid G. Voskressensky

  DOI：10.1002/ejoc.201901776

  日期：2020.3.8

  Herein, a new route toward 2,4‐substituted pyrroles is presented. This is a new, simple, fast, and convenient method furnishing 2,4‐substituted pyrroles based on the formal cycloaddition reaction of isocyanides with acyclic enamines or enaminones under basic conditions.

  在此，提出了一种新的制备2,4-取代吡咯的途径。这是在异氰酸酯与无环烯胺或烯胺酮在碱性条件下正式环加成反应的基础上，提供2,4-取代吡咯的一种新的，简单，快速和方便的方法。
• A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone <i>via</i> 6π electrocyclization
  作者：Jiarui Sun、Xiangsheng Cheng、John Kamanda Mansaray、Weihong Fei、Jieping Wan、Weijun Yao

  DOI：10.1039/c8cc06868b

  日期：——

  sulfonyl azide to construct iminolactone via a cascade process involving copper-catalyzed alkyne–azide cycloaddition (CuAAC), Michael addition of metalated ketenimine followed by elimination and 6π electrocyclization.

  我们开发了一种铜催化的芳基乙炔，烯胺酮和磺酰叠氮化物的三组分反应，通过级联工艺来构建亚氨基内酯，该工艺涉及铜催化的炔炔叠氮化物环加成反应（CuAAC），金属加成的酮亚胺的迈克尔加成反应，然后消除和6π电环化。
• Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5-<i>b</i>]quinolines via an I₂-Promoted One-Pot Multicomponent Reaction
  作者：Peng Zhao、Xia Wu、You Zhou、Xiao Geng、Can Wang、Yan-dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.9b00685

  日期：2019.4.19

  The first synthesis of 2,3-diaroyl quinolines via a formal [3 + 2 + 1] cycloaddition of enaminones, aryl methyl ketones, and aryl amines is disclosed. This reaction efficiently affords a 1,4-dicarbonyl scaffold, which is a useful building block for constructing complex fused heterocycles. Furthermore, the 1,4-dicarbonyl scaffold has been used directly to prepare pyridazino[4,5-b]quinoline skeletons

  公开了通过烯胺酮，芳基甲基酮和芳基胺的正式[3 + 2 + 1]环加成的2，3-二酰基酰基喹啉的首次合成。该反应有效地提供了1，4-二羰基支架，这是用于构建复杂的稠合杂环的有用的构建基。此外，已将1，4-二羰基支架直接用于一锅制备哒嗪并[4,5- b ]喹啉骨架。
• Iodine-mediated synthesis of sulfur-bridged enaminones and chromones via double C(sp²)–H thiolation
  作者：Yong Gao、Li Wei、Yunyun Liu、Jie-Ping Wan

  DOI：10.1039/c7ob00619e

  日期：——

  reactions of various enaminones with elemental sulfur giving rise to both sulfur-bridged enaminones and chromones have been realized via iodine promotion. All products were furnished by means of double C(sp2)–H bond thiolation without using any metal catalyst or sensitive oxidant, providing a simple and efficient protocol for the synthesis of diverse sulfur derivatives of enaminones.

  通过碘的促进已经实现了各种烯胺酮与元素硫的反应，其同时引起硫桥联的烯胺酮和色酮。所有产品均通过双C（sp 2）-H键硫醇化而无需使用任何金属催化剂或敏感氧化剂即可提供，为合成烯胺酮的多种硫衍生物提供了简单有效的方案。