2,5-双甲氧酰基-3,4-二苯基环戊二烯酮 | 16691-79-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2,5-双甲氧酰基-3,4-二苯基环戊二烯酮
• 中文别名: 2,5-二(甲氧羰基)-3,4-二苯基环戊二酮；3,4-二苯基环戊二烯酮-2,5-二羧酸二甲酯；2,5-双(甲氧酰基)-3,4-二苯基环戊二烯酮
• 英文名称: 2,5-bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
• 英文别名: 2,5-dicarbomethoxy-3,4-diphenylcyclopentadienone；2-oxo-4,5-diphenyl-cyclopenta-3,5-diene-1,3-dicarboxylic acid dimethyl ester；dimethyl 2-oxo-4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate
• CAS: 16691-79-5
• 化学式: C₂₁H₁₆O₅
• mdl: MFCD00111095
• 分子量: 348.355
• InChiKey: NTXFYWYVVGMAGT-UHFFFAOYSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  445.4±45.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.095
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2918300090
• 储存条件：
  室温且干燥环境中保存

SDS

2,5-Bis(methoxycarbonyl)-3,4-
diphenylcyclopentadienone
SAFETY DATA SHEET

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Section 1. IDENTIFICATION OF THE SUBSTANCE OR MIXTURE AND OF THE SUPPLIER
Product name: 2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
Not classified
PHYSICAL HAZARDS
HEALTH HAZARDS Not classified
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
None
Pictograms or hazard symbols
Signal word No signal word
Hazard statement None
Precautionary statements None

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
2,5-Bis(methoxycarbonyl)-3,4-diphenylcyclopentadienone
Component(s):
Percent: ....
16691-79-5
CAS Number:
Synonyms: Dimethyl 3,4-Diphenylcyclopentadienone-2,5-dicarboxylate , 3,4-
Diphenylcyclopentadienone-2,5-dicarboxylic Acid Dimethyl Ester
Chemical Formula: C21H16O5

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Get medical advice/attention if you feel unwell. Rinse mouth.
Ingestion:
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
2,5-Bis(methoxycarbonyl)-3,4-
diphenylcyclopentadienone

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Section 5. FIRE-FIGHTING MEASURES
Specific methods: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Law is followed.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form: crystal - powder
Color: Yellow - Yellow red
Odor: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling Point/Range: No data available
Flash Point: No data available
Explosive limits
Lower: No data available
Upper: No data available
Density: No data available
Solubility: No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Stability:
Reactivity: No special reactivity has been reported.
Incompartible materials: oxidizing agents
2,5-Bis(methoxycarbonyl)-3,4-
diphenylcyclopentadienone

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Section 10. STABILITY AND REACTIVITY
Hazardous Decomposition Carbon monoxide, Carbon dioxide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobillity in soil
log Pow: No data available
No data available
Soil adsorption (Koc):
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
Not Listed
UN-No:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.
2,5-Bis(methoxycarbonyl)-3,4-
diphenylcyclopentadienone

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-双甲氧酰基-3,4-二苯基环戊二烯酮 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 0.42h， 以57%的产率得到dimethyl 4,5-diphenylcyclopenta-3,5-diene-1,3-dicarboxylate
  参考文献：
  名称：

  Demonstration of the facile reversibility of fulvene formation

  摘要：

  Cleavage of fulvenes under mild conditions and interchange between electron-deficient fulvenes and their constituent cyclopentadienes and imines is demonstrated for the first time. A series of cyclopentadienes and imines are investigated to probe the dependence of fulvene equilibration on structure. The exchange of one fulvene for another is demonstrated in the first reported example of transfulvenation. Finally, the metathesis of two fulvenes to generate all four possible cross products is shown. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.094
• 作为产物：
  描述：

  dimethyl 5-hydroxy-2-methoxy-4,5-diphenylcyclopenta-1,3-diene-1,3-dicarboxylate 在 高氯酸 作用下， 生成 2,5-双甲氧酰基-3,4-二苯基环戊二烯酮
  参考文献：
  名称：

  Eistert,B.; Thommen,A.J., Chemische Berichte, 1971, vol. 104, p. 3048 - 3061

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-phenoxy-2-ethyl-2,3-dihydro-1,3,2λ5-benzoxazaphosphole 在 2,5-双甲氧酰基-3,4-二苯基环戊二烯酮 作用下， 以 苯 为溶剂， 反应 0.02h， 以92%的产率得到Dimethyl 2-oxo-4,5-diphenylcyclopent-3-ene-1,3-dicarboxylate
  参考文献：
  名称：

  Fuzhenkova, A. V.; Tyryshkin, N. I.; Terent'eva, S. A., Russian Journal of General Chemistry, 1993, vol. 63, # 5.1, p. 740 - 742

  摘要：

  DOI：

文献信息

• Frontier-controlled cycloaddition reactions of cyclopentadienones having electron-donating or -attracting substituents: configuration of adducts and kinetic studies
  作者：Masato Mori、Ayako Hayamizu、Ken Kanematsu

  DOI：10.1039/p19810001259

  日期：——

  inverse electron demand. By contrast, in the correlation for the cycloaddition of (1b) with (2a–h), two lines with markedly different slopes were observed, which can be ascribed to a Diels–Alder reaction with neutral electron demand. The initial cycloadditions of (1a) and (1b) with tropone (29) gave the [4 + 6]π adducts (32a,b). Subsequently the adduct (32b) underwent oxy-Cope rearrangement to (35). The

  2，5-二甲氧基羰基-和2，5-二乙基-3,4-二苯基环戊二烯酮[CPC（1a）和EPC（1b）]与对位取代的苯乙烯（2a–h）的环加成反应产生的主要加合物的立体化学证实降冰片二烯（7），降冰片烯（8），1，4-二氢-1，4-环氧萘（9），马来酸酐（10）和N-苯基马来酰亚胺（11）具有内构型。为了定义取代基对Diels-Alder反应速率的影响，对（1a，b）与一系列苯乙烯（2a-h）的反应性进行了动力学研究。（1a）与（2a–h）的环加成的对数k / k H值与冈本布朗的σp +相关常数和ρ值为–0.941。该结果表明，环加成反应被归类为具有反电子需求的Diels-Alder反应。相比之下，在（1b）与（2a–h）的环加成反应的相关性中，观察到两条斜率明显不同的线，这可以归因于具有中性电子需求的Diels–Alder反应。（1a）和（1b）与对苯二酚（29）的初始环加成反应产生[4 +
• Effect of >CO···H–Ar interaction on endo/exo selectivity in the Diels–Alder reaction of phenyl-substituted cyclopentadienones
  作者：Yasuyuki Yoshitake、Hidetoshi Nakagawa、Masashi Eto、Kazunobu Harano

  DOI：10.1016/s0040-4039(00)00602-x

  日期：2000.6

  e with S-allyl S-methyl dithiocarbonate gave the endo cycloadduct whereas phencyclone gave a mixture of the endo and exo cycloadducts. The X-ray analysis of the cycloadduct of phencyclone and S-allyl S-methyl dithiocarbonate indicated the presence of a short contact of Ar–H···OC< type. A possible role of the interaction in determining the endo/exo selectivity was discussed based on the X-ray crystallographic

  的2,5-双（甲氧基羰基）-3,4- diphenylcyclopentadienone与环加成小号-烯丙基小号-甲基二硫代碳酸酯，得到内型环加成而phencyclone得到的混合物内切和外切cycloadducts。X射线分析苯环酮和S-烯丙基S-甲基二硫代碳酸酯的环加合物表明存在Ar–H···OC<类型的短接触。基于X射线晶体学数据和MO计算数据的过渡结构，讨论了相互作用在确定内/外选择性方面的可能作用。
• Synthesis of a C₅₆H₄₀ Hydrocarbon Bearing a 54-Carbon Framework of C₆₀
  作者：Kung K. Wang、Yu-Hsuan Wang、Hua Yang、Novruz G. Akhmedov、Jeffrey L. Petersen

  DOI：10.1021/ol900749a

  日期：2009.6.18

  A C56H40 hydrocarbon possessing a 54-carbon framework represented on the surface of C60 was synthesized by solution-phase chemistry. The structure of this hydrocarbon has a 30-carbon core, which can be regarded as a partially hydrogenated [5,5]circulene, a C30H12 semibuckminsterfullerene, with only one of the carbon−carbon bonds remaining unconnected. The central 30-carbon core is fused with two indeno

  通过溶液相化学合成了在C 60表面具有54碳骨架的AC 56 H 40烃。该碳氢化合物的结构具有30个碳核，可以看作是部分氢化的[5,5]环戊烯，一种C 30 H 12半buckminsterfullerene，仅其中一个碳-碳键保持未连接状态。中心的30个碳原子核稠合有两个茚基，并带有两个苯基和两个甲基取代基。
• Cascade Radical Cyclizations of Benzannulated Enyne−Allenes. Unusual Cleavage of a Benzene Ring Leading to Twisted 1,1‘-Dialkyl-9,9‘-bifluorenylidenes and Spiro[1<i>H</i>-cyclobut[<i>a</i>]indene-1,9‘-[9<i>H</i>]fluorenes]
  作者：Yonghong Yang、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/jo030147j

  日期：2003.7.1

  9'-[9H]fluorene] 20 apparently was produced via two intramolecular [2 + 2] cycloaddition reactions of the benzannulated enyne-allene moieties, generated in situ from the benzannulated enediynyl propargylic alcohols. The twisted 1,1'-dimethyl-9,9'-bifluorenylidene 33 and the spiro[1H-cyclobut[a]indene-1,9'-[9H]fluorene] 39 (trans/cis = 3:1) were likewise produced from 32 and 38, respectively.

  用亚硫酰氯处理苯并环化的二炔基炔丙醇16（异构体比例= 2：1），引发一系列反应，导致扭曲的1,1'-二丙基-9,9'-联芴基17，多环化合物18和19，和螺[1H-环丁[a]茚-1,9'-[9H]芴] 20（反式/顺式= 5：1）。从16到出乎意料的17的转变大概涉及苯甲环烯-烯丙烯21的初始形成，然后进行C（2）-C（6）环化反应和分子内自由基-自由基偶联反应，从而形成正式的Diels- Alder加合物23。重复该序列，然后提供24。连接具有丙基取代基的两个碳的键的断裂得到25。随后，连接两个中心五元环的碳-碳键的旋转随后得到反式异构体26 。26可能被氧气氧化，然后水解，然后生成17。有趣的是，导致17的途径涉及苯环的不寻常裂解。17的X射线晶体结构表明，其对于连接两个联芴基片段的碳-碳双键具有45.2度的扭转角。螺[1H-环丁[a]茚-1,9'-[9H]芴] 20显然是由苯并环烯炔-丙二烯部分的两个分子内[2
• Studies on Seven-Membered Heterocycles. XXXIV. Syntheses and Reactions of 1-Benzosilepines, 1-Benzogermepines, 1-Benzophosphepines, and 1-Benzarsepines.
  作者：Shin-ichi SHIRATORI、Shuji YASUIKE、Jyoji KURITA、Takashi TSUCHIYA

  DOI：10.1248/cpb.42.2441

  日期：——

  Flash vacuum pyrolysis of 2a, 7b-dihydrocyclobuta[b]-1-benzometalloles (6a-e), prepared from the corresponding 1-benzometalloles (3) containing Si, Ge, P, or As via three steps, resulted in valence isomerization with ring-opening to give 1, 1-dimethyl-1-benzosilepine (7a), 1-methyl-1-phenyl-1-benzosilepine (7b), 1, 1-dimethyl-1-benzogermepine (7c), 1-phenyl-1-benzophosphepine 1-oxide (7d), and 1-phenyl-1-benzarsepine 1-oxide (7e). The oxides (7d, e), on treatment with trichlorosilane, underwent deoxygenation to afford 1-phenyl-1-benzophosphepine (7f) and 1-phenyl-1-benzarsepine (7g). The 1-benzometallepines (7a-g) thus obtained are hitherto unknown heterocyclic ring compounds, and their thermal stabilities and several reactions were examined.

  采用快速真空热解法处理由硅、锗、磷或砷的1-苯并金属烯（3）经三步反应制备的2a, 7b-二氢环丁并[b]-1-苯并金属烯（6a-e），导致价态异构化及环的开裂，得到1, 1-二甲基-1-苯并硅宾烯（7a）、1-甲基-1-苯基-1-苯并硅宾烯（7b）、1, 1-二甲基-1-苯并锗宾烯（7c）、1-苯基-1-苯并膦宾烯1-氧化物（7d）和1-苯基-1-苯并砷宾烯1-氧化物（7e）。这些氧化物（7d, e）在三氯硅烷处理后，经历脱氧过程，产生1-苯基-1-苯并膦宾烯（7f）和1-苯基-1-苯并砷宾烯（7g）。获得的1-苯并金属烯（7a-g）是迄今为止未知的杂环化合物，且研究了它们的热稳定性和若干反应。

表征谱图