二苯基环丙烯酮 | 61440-88-8

• 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: 二苯基环丙烯酮
• 英文名称: bis(2,4,6-trimethylphenyl)cyclopropenone
• 英文别名: 2,3-dimesitylcyclopropenone；1,2-dimesitylcyclopropenoe；dimesitylcyclopropenone；2,3-Dimesitylcycloprop-2-enone；2,3-bis(2,4,6-trimethylphenyl)cycloprop-2-en-1-one
• CAS: 61440-88-8
• 化学式: C₂₁H₂₂O
• 分子量: 290.405
• InChiKey: LXCSCXXFUGZMQN-UHFFFAOYSA-N

物化性质

• 沸点：
  392.48°C (rough estimate)
• 密度：
  1.0066 (rough estimate)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 储存条件：
  存储于0至6℃的阴凉干燥处。

SDS

Name:	Dimesitylcyclopropenone 97% Material Safety Data Sheet
Synonym:	None Known
CAS:	61440-88-8

Section 1 - Chemical Product MSDS Name:Dimesitylcyclopropenone 97% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
61440-88-8	Dimesitylcyclopropenone	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
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. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use carbon dioxide, dry chemical powder or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 61440-88-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Chunks
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C21H24O
Molecular Weight: 292.1674

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 61440-88-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Dimesitylcyclopropenone - Not listed by ACGIH, IARC, or NTP.

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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# 61440-88-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 61440-88-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 61440-88-8 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：

  二苯基环丙烯酮 以 苯 为溶剂， 生成 1,2-dimesitylethyne
  参考文献：
  名称：

  乙炔与过渡金属的反应：二芳基乙炔低聚中的VII空间效应

  摘要：

  描述了邻取代的二苯基乙炔的合成及其对二氯双（苄腈）钯（II）的行为。讨论了空间因素对低聚的影响。

  DOI：

  10.1016/s0022-328x(00)87216-2
• 作为产物：
  描述：

  3-chloro-3-triphenylphosphonio-1,2-dimesitylcyclopropene chloride 在 水 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以100%的产率得到二苯基环丙烯酮
  参考文献：
  名称：

  环丙烯鎓取代的鏻盐的反应性与稳定性

  摘要：

  报道了亲电 3-(三苯基膦)-环丙烯盐对中性亲核试剂 (如三苯基膦) 的稳定性与反应性。根据环丙烯基取代基 (R) 的性质，三元环结构被保留 (R = Ph) 或通过开环演变为异构线性丙二烯 (R = Mes)。1,3-双(三苯基膦)-2,3-二苯基环丙烯和3,3-双(三苯基膦)-1,1-二甲基二亚苯基产物的各自形成基于空间和静电约束合理化。

  DOI：

  10.1002/ejic.201900867
• 作为试剂：
  描述：

  苯甲酸 在 光气 、 二苯基环丙烯酮 作用下， 反应 6.0h， 以99%的产率得到苯甲酰氯
  参考文献：
  名称：

  一种用于羧酸光气化反应制备羧酸酰氯的催化剂及其应用

  摘要：

  本发明公开了一种用于羧酸光气化反应制备羧酸酰氯的催化剂及其应用。本发明提供了一种羧酸与光气经光气化反应制备羧酸酰氯的方法，其使用如式I和/或式II所示的化合物作为催化剂，其中，R1、R2、R3、R4、R5、R6独立地为氢或C1‑C6的烷基。本发明的方法可以在相对温和的条件下促进光气与羧酸的反应，提高反应效率，理论上不会产生高度敏感的致癌物NDMA，且使用常规的HPLC方法即可跟踪催化剂去向，从而保证酰氯产品的安全；本发明还提供了一种化合物，2,3‑双(2,6‑二甲基‑4‑异丙基苯基)环丙‑2‑烯‑1‑酮或2,3‑双(2,6‑二甲基‑4‑叔丁基苯基)环丙‑2‑烯‑1‑酮。

  公开号：

  CN114573449A

文献信息

• Highly Efficient Photochemical Generation of a Triple Bond:  Synthesis, Properties, and Photodecarbonylation of Cyclopropenones
  作者：Andrei Poloukhtine、Vladimir V. Popik

  DOI：10.1021/jo034869m

  日期：2003.10.1

  The latter then rapidly loses carbon monoxide to produce the ultimate acetylenic product. Despite their high photoreactivity, cyclopropenones were found to be thermally stable compounds with the exception of hydroxy- and methoxy-substituted cyclopropenones. The latter undergo rapid solvolysis in hydroxylic solvents even at room temperature. The application of this reaction to the in situ generation

  烷基，芳基和杂原子取代的环丙烯酮的UV照射导致一氧化碳损失并形成相应炔烃的定量收率。光化学脱羰反应的量子产率从烷基取代的环丙烯酮的20％到30％到二苯基和二萘基环戊烯酮的70％以上。通过使用激光闪光光解法观察到该反应中中间体迅速形成（<5 ns），然后稍微慢一些（约40 ns）衰变。DFT计算使我们能够将这种中间体鉴定为由环丙烯酮环的碳-碳键之一裂解形成的两性离子物质。后者然后迅速损失一氧化碳以产生最终的炔属产物。尽管它们的光反应性很高，除羟基和甲氧基取代的环丙烯酮外，发现环丙烯酮是热稳定的化合物。后者甚至在室温下也能在羟基溶剂中进行快速溶剂分解。该反应对苯二炔结构原位生成的应用通过苯并二烯化的苯二炔12的光化学制备进行了说明。
• Nucleophilic Acyl Substitution via Aromatic Cation Activation of Carboxylic Acids: Rapid Generation of Acid Chlorides under Mild Conditions
  作者：David J. Hardee、Lyudmila Kovalchuke、Tristan H. Lambert

  DOI：10.1021/ja101292a

  日期：2010.4.14

  occurs rapidly in the presence of 3,3-dichlorocyclopropenes via the intermediacy of cyclopropenium carboxylate complexes. The effect of cyclopropene substituents on the rate of conversion is examined. The addition of tertiary amine base is found to dramatically accelerate reaction, and conditions were developed for the preparation of acid sensitive acid chlorides. Preparative scale peptide couplings of

  已实现芳香族阳离子活化亲核酰基取代的第一个实例。在 3,3-二氯环丙烯的存在下，通过环丙烯鎓羧酸盐络合物的中介作用，羧酸迅速转化为其相应的酰氯。检查了环丙烯取代基对转化率的影响。发现叔胺碱的加入显着加速了反应，并开发了制备酸敏感酰氯的条件。用这种方法实现了两个 N-Boc 氨基酸的制备规模的肽偶联。
• C₆H₄ Valence Bond Isomers:  A Reactive Bicyclopropenylidene
  作者：Brian Halton、Mark J. Cooney、Carissa S. Jones、Roland Boese、Dieter Bläser

  DOI：10.1021/ol048307g

  日期：2004.10.1

  [reaction: see text] The simple bicyclopropenylidene derivative 21b, stabilized by fusion into naphthalene, results from reaction of dimesitylcyclopropenone 20b with the 1-trimethylsilyl-1H-cyclopropa[b]naphthalenyl anion. Although unstable in air, the molecule survives ambient conditions long enough for separation and mass spectral characterization. Aerial oxidation of 21b leads to 2,3-dimesitylanthracene-1

  [反应：见正文]由二聚环戊烯酮20b与1-三甲基甲硅烷基-1H-环丙烷[b]萘基阴离子的反应生成的，通过与萘融合而稳定的简单的双环丙烯基衍生物21b。尽管该分子在空气中不稳定，但它在环境条件下生存的时间足够长，足以进行分离和质谱表征。21b的空气氧化导致2，3-二甲基蒽-1，4-二酮22b的X射线晶体结构已经确定。虽然二苯基环丙烯酮20a未提供可识别的产物，但二叔丁基类似物20c提供了醌22c，但收率较低。
• Chlorofluorocarbene addition to alkynes: a novel path to cyclopropenones with uncommon substituents (cyclopropenone chemistry, part 11)
  作者：Eckehard V. Dehmlow、Andreas Winterfeldt

  DOI：10.1016/s0040-4020(01)80121-6

  日期：1989.1

  Phase transfer catalytically generated chlorofluorocarbene adds to alkynes much more readily than dichlorocarbene. Some sterically shielded or critically substituted compounds that do not give addition with CCl2 can be reacted with CClF. Chlorofluorocyclopropenes thus formed are hydrolyzed to cyclopropenones in situ. Hitherto unknown α-oxygen functional cyclopropenones were also prepared for the first

  相转移催化生成的氯氟卡宾比二氯卡宾更容易添加炔烃。某些不与CCl 2加成的空间屏蔽或临界取代的化合物可以与CClF反应。由此形成的氯氟环丙烯原位水解为环丙烯酮。迄今为止，还首次制备了未知的α-氧官能环丙烯酮。然而，分离α-羰基取代的环丙烯酮的尝试失败了：显然，吸电子基团使半芳族体系不稳定。
• Indolizines. 3. Oxidation products of indolizinols: radicals, ions, and oxidized dimers
  作者：Donald H. Wadsworth、Charles H. Weidner、Steven L. Bender、Robert H. Nuttall、Henry R. Luss

  DOI：10.1021/jo00276a028

  日期：1989.7