反-1,2-二苯酰乙烯 | 959-28-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酮
• 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: 反-1,2-二苯酰乙烯
• 中文别名: 反-1,2-二苯甲酰乙烯；反式-1,4-二苯基-2-丁烯-1,4-二酮；反-1,4-二苯基-2-丁烯-1,4-二酮；1,2-联苯甲酰乙烯
• 英文名称: 1,4-diphenylbut-2-ene-1,4-dione
• 英文别名: trans-1,2-dibenzoylethylene；(E)-1,4-diphenylbut-2-ene-1,4-dione
• CAS: 959-28-4
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: WYCXGQSQHAXLPK-VAWYXSNFSA-N

物化性质

• 熔点：
  109-112 °C(lit.)
• 沸点：
  338.73°C (rough estimate)
• 密度：
  1.1223 (rough estimate)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29143900
• RTECS号：
  EM7000000
• 储存条件：
  应储存在冷干燥环境中，并放置于通风良好、远离加热源及不相容物质的地方，密封保存。

SDS

Name:	Trans-1 2-Dibenzoylethylene 97% Material Safety Data Sheet
Synonym:	1, 4-Diphenyl-2-Butene-1, 4 Dione
CAS:	959-28-4

Section 1 - Chemical Product MSDS Name:Trans-1 2-Dibenzoylethylene 97% Material Safety Data Sheet
Synonym:1, 4-Diphenyl-2-Butene-1, 4 Dione

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
959-28-4	2-Butene-1,4-Dione, 1,4-Diphenyl-, (e)	97	213-498-1

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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

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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:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. 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 tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 959-28-4: 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 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
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 108.00 - 111.00 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:
Specific Gravity/Density:
Molecular Formula: C16H12O2
Molecular Weight: 236.27

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 959-28-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Butene-1,4-Dione, 1,4-Diphenyl-, (e)- - 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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 959-28-4: No information available.
Canada
CAS# 959-28-4 is listed on Canada's NDSL List.
CAS# 959-28-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 959-28-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质：

• 黄色针状晶体，熔点为111℃。

用途：

• 用作有机合成中间体。

生产方法：

• 通过反丁烯二酰氯与苯在无水三氯化铝的存在下反应制得，产率为78%-83%。

反应信息

• 作为反应物：
  描述：

  反-1,2-二苯酰乙烯 在 PPA 作用下， 以 苯 为溶剂， 反应 5.17h， 生成 1,3-二苯基异苯并呋喃
  参考文献：
  名称：

  A New Synthesis of 1,3-Diarylisobenzofurans

  摘要：

  DOI：

  10.1055/s-1980-28946
• 作为产物：
  描述：

  2-二氮杂-1-苯乙酮 在 copper dichloride 、 苯 作用下， 生成 反-1,2-二苯酰乙烯
  参考文献：
  名称：

  Diazoketones as Reagents for the Identification of Organic Acids

  摘要：

  DOI：

  10.1021/ja01155a086

文献信息

• Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid
  作者：Ramanathan Prasanna、Somraj Guha、Govindasamy Sekar

  DOI：10.1021/acs.orglett.9b00635

  日期：2019.4.19

  transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

  已经开发了在无过渡金属的条件下使用黄原酸酯/甲酸混合物通过质子耦合电子转移（PCET）将α，β-不饱和酮化学选择性还原为饱和酮并将炔烃立体选择性还原为（E）烯烃的方法。 ）。机械实验和DFT计算支持协调的质子电子转移（CPET）途径的可能性。这种桦木型还原表明，小的亲核有机分子可以用作具有适当质子源的单电子转移（SET）还原剂。
• AlCl₃-Promoted Conjugate Reduction of α,β Unsaturated Carbonyl Compounds with 1,3-Dimethyl-2-phenylbenzimidazoline
  作者：Hidenori Chikashita、Kazuyoshi Itoh

  DOI：10.1246/bcsj.59.1747

  日期：1986.6

  substrates. The catalytic efficiency of Lewis acids was found to be proportional to the efficiency to form a complex with a carbonyl group. The reduction of 2-cinnamoylpyridine with 2-deuterated DMBI revealed that in the reduction product, a deuterium atom was located at the β-position with respect to the carbonyl group. On the other hand, the reduction of the same substrate with DMBI followed by quenching

  以1,3-二甲基-2-苯基苯并咪唑啉（DMBI）为还原剂，将除α,β-不饱和醛外的多种α,β-不饱和羰基化合物还原为相应的饱和羰基化合物在 AlCl3 的帮助下。基于 DMBI 的氢化物供体能力以及 AlCl3 作为底物的亲电活化剂的作用讨论了还原反应。发现路易斯酸的催化效率与与羰基形成络合物的效率成正比。用 2-氘代 DMBI 还原 2-肉桂酰基吡啶表明，在还原产物中，氘原子位于羰基的 β 位。另一方面，用 DMBI 还原相同的底物，然后用 D2O 淬灭，得到在 α 位含有氘标记的还原产物。这些结果被解释为涉及烯醇中间体产生的机制......
• A Broad‐Spectrum Synthesis of Tetravinylethylenes
  作者：Kelsey L. Horvath、Christopher G. Newton、Kimberley A. Roper、Jas S. Ward、Michael S. Sherburn

  DOI：10.1002/chem.201900550

  日期：2019.3.15

  compounds of the tetravinylethylene (TVE) family is reported. Ramirez‐type dibromo‐olefination of readily accessible penta‐1,4‐dien‐3‐ones generates 3,3‐dibromo[3]dendralenes, which undergo twofold Negishi, Suzuki–Miyaura or Mizoroki–Heck reactions with a wide variety of olefinic coupling partners. This route delivers a broad range of unsymmetrically substituted tetravinylethylenes with up to three

  报道了四乙烯基乙烯（TVE）家族化合物的第一个一般合成。容易获得的五-1,4-二烯-3-酮的拉米雷斯型二溴烯烃化反应生成3,3-二溴[3]树枝状烯，它们经历了两次Negishi，Suzuki-Miyaura或Mizoroki-Heck反应，并带有多种烯烃耦合伙伴。该途径提供了范围广泛的不对称取代的四乙烯基乙烯，其具有多达三个不同的烯基取代基连接至中央C = C键。该方法的广泛范围通过制备第一个更高阶的通过共轭/交叉共轭杂化化合物形成的低级烯烃。显示不对称取代的TVE经历了具有高位点选择性和非对映选择性的多米诺骨化电环化反应，
• Organocatalyzed Enantioselective Michael Addition of 2‐Hydroxypyridines and α,β‐Unsaturated 1,4‐Dicarbonyl Compounds
  作者：Yu‐Chun Wu、Yi Jhong、Hui‐Jie Lin、Sharada Prasanna Swain、Hui‐Hsu Gavin Tsai、Duen‐Ren Hou

  DOI：10.1002/adsc.201900997

  日期：2019.11.5

  prevalent in biologically and medicinally important molecules. Here we report that chiral N‐substituted 2‐pyridones were prepared by enantioselective, organocatalytic aza‐Michael additions of halogenated 2‐hydroxypyridines (pyridin‐2(1H)‐ones) to α,β‐unsaturated‐1,4‐dketones or 1,4‐ketoesters. The reactions were optimized by the choice of solvents and systematic screening of Cinchona alkaloid‐based bifunctional

  2-吡啶酮的结构普遍存在于生物学和医学上重要的分子中。在这里我们报道了手性的N取代的2-吡啶酮是通过将对卤化的2-羟基吡啶（吡啶2（1 H）-一个）进行对映选择性的有机催化氮杂Michael加成反应而制备的，形成α，β-不饱和的1,4,4-酮或1,4-酮酸酯。通过选择溶剂和系统筛选基于金鸡纳生物碱的双功能催化剂，可以优化反应，以实现出色的收率和对映选择性（最高收率98％，ee≥99％）。密度泛函理论计算为观察到的对映选择性提供了理论依据。使用通过该方法产生的手性迈克尔加合物，可以实现人鼻病毒蛋白酶抑制剂的正式合成。
• Reduction of<i>α</i>-Halo Carbonyl Compounds with NaBH₄-SbBr₃
  作者：Shinsei Sayama、Yutaka Inamura

  DOI：10.1246/cl.1996.633

  日期：1996.8

  The reagent NaBH4-SbBr3 was found to be chemoselective for the reductive debromination of aromatic α-bromo carbonyl compounds and 2,3-dibromo-1,4-butanediones.

  发现试剂 NaBH4-SbBr3 对芳香族 α-溴羰基化合物和 2,3-二溴-1,4-丁二酮的还原脱溴具有化学选择性。

表征谱图