4-[(4-氟苯基)亚甲基]-2-苯基恶唑-5(4H)-酮 | 449-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-[(4-氟苯基)亚甲基]-2-苯基恶唑-5(4H)-酮
• 英文名称: 4-(4-fluorobenzylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: 4-[(4-Fluorophenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 449-81-0
• 化学式: C₁₆H₁₀FNO₂
• mdl: MFCD00020886
• 分子量: 267.259
• InChiKey: GGMAOSAZKMNBHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name 4-(4-FLUOROBENZYLIDENE)-2-PHENYL-2-OXAZ&

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2 - Hazards Identification

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
4-(4-FLUOROBENZYLIDENE)-2-PHENYL-2 449-81-0 207-189-0 None
-OXAZOLIN-5-ONE
Formula C16H10FNO2
Molecular Weight 267,2600 AMU
Synonyms 4-(p-Fluorobenzylidene)-2-phenyl-2-oxazolin-5-one

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER SKIN CONTACT
In case of contact, immediately wash skin with soap and copious
amounts of water.
AFTER EYE CONTACT
In case of contact, immediately flush eyes with copious amounts
of water for at least 15 minutes.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: Water spray. Carbon dioxide, dry chemical powder, or
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appropriate foam.
SPECIAL RISKS
Specific Hazard(s): Emits toxic fumes under fire conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear respirator, chemical safety goggles, rubber boots, and
heavy rubber gloves.
METHODS FOR CLEANING UP
Sweep up, place in a bag and hold for waste disposal. Avoid
raising dust. Ventilate area and wash spill site after material
pickup is complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Avoid inhalation. Avoid contact
with eyes, skin, and clothing. Avoid prolonged or repeated
exposure.
STORAGE
Conditions of Storage: Keep tightly closed. Store in a cool dry
place.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Mechanical exhaust required.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling. Wash contaminated clothing before
reuse.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Respiratory protection is not required. Where
protection is desired, use multi-purpose combination (US) or type
ABEK (EN 14387) respirator cartridges.
Hand Protection: Compatible chemical-resistant gloves.
Eye Protection: Chemical safety goggles.

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range N/A
MP/MP Range 184,000. - 186,000 °
C.
Flash Point N/A
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
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Explosion Limits N/A
Vapor Pressure N/A
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Materials to Avoid: Strong oxidizing agents.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide,
Nitrogen oxides, Hydrogen fluoride.

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11 - Toxicological Information

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RTECS NUMBER: RQ5796000
ACUTE TOXICITY
LD50
Intravenous
Mouse
100 MG/KG
SIGNS AND SYMPTOMS OF EXPOSURE
To the best of our knowledge, the chemical, physical, and
toxicological properties have not been thoroughly investigated.
ROUTE OF EXPOSURE
Skin Contact: May cause skin irritation.
Eye Contact: May cause eye irritation.
Multiple Routes: May be harmful by inhalation, ingestion, or
skin absorption.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and
scrubber. Observe all federal, state, and local environmental
regulations.

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14 - Transport Information

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RID/ADR
Non-hazardous for road transport.
IMDG
Non-hazardous for sea transport.
IATA
Non-hazardous for air transport.

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15 - Regulatory Information

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COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-[(4-氟苯基)亚甲基]-2-苯基恶唑-5(4H)-酮 在 尿素 作用下， 以 乙二醇 为溶剂， 反应 0.08h， 以84%的产率得到4-(4-fluorobenzylidene)-2-phenyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  级联反应的扩展：GFP生色团衍生物的微波辅助合成

  摘要：

  咪唑-5（4 H）-1衍生物的微波辅助简便合成是通过4-芳基亚甲基-2-苯基恶唑-5（4 H）-1与脲（或醋酸铵）在乙二醇中的反应完成的。级联反应易于进行，并且在温和条件下发生，适用范围广。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.315
• 作为产物：
  描述：

  在 1,1,3,3-四甲基二硅氧烷 、 copper(II) bis(trifluoromethanesulfonate) 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以72%的产率得到4-[(4-氟苯基)亚甲基]-2-苯基恶唑-5(4H)-酮
  参考文献：
  名称：

  酸酐的催化氮杂-Wittig反应合成4 H-苯并[ d ] [1,3]恶嗪-4-酮和4-苄叉基-2-芳基恶唑-5（4 H）-酮

  摘要：

  与醛，酮，酰胺和酯的aza-Wittig反应相比，酸酐的aza-Wittig反应总是被忽略，这应该是Wittig反应的重要组成部分。在这里，酸酐的aza-Wittig反应和酸酐的aza-Wittig催化反应均以高收率开发，这为合成4 H-苯并[ d ] [1,3]恶嗪-4-酮和4-亚苄基-2-芳基恶唑-5（4 H）-那些。使用了铜催化的氧化膦还原的策略，发现该策略对这种转化有效。另外，实现了羧酸的一锅催化的氮杂-维蒂希反应。此外，NMR实验和Hammett曲线记录了酸酐的催化氮杂-维蒂希反应过程，这直接证明了铜催化的废氧化膦的还原是该转化过程中的关键步骤。

  DOI：

  10.1021/acscatal.6b00165

文献信息

• Greener approach: Ionic liquid [Et₃NH][HSO₄]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4<i>H</i>)oxazolones under solvent-free condition
  作者：Santosh A. Jadhav、Aniket P. Sarkate、Mazahar Farooqui、Devanand B. Shinde

  DOI：10.1080/00397911.2017.1340649

  日期：2017.9.17

  chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method. GRAPHICAL ABSTRACT

  摘要 我们开发了简单、更环保、更安全的多组分合成系列 4-亚芳基-2-苯基-5(4H) 恶唑酮 4(ar) 以三乙基硫酸氢铵 [Et3NH][HSO4] 为催化的布朗斯台德酸离子液体和催化量的乙酸酐和乙酸钠，产率极好（90-99%）。该协议提供了经济、环境友好、无溶剂的条件，以及催化剂的回收再利用，并且从苯甲酰氯 1、氨基酸 2 和各种醛 3 开始很容易获得。 环化后苯甲酰氯、氨基酸的缩合，以及由ILs [Et3NH][HSO4]和催化量的乙酸酐和乙酸钠催化的多种醛。最终产物通过其表征数据如 FTIR、1H-NMR、13C-NMR、Mass、高分辨率质谱，并与其报道的方法进行了比较。图形概要
• A simple and efficient method for the synthesis of Erlenmeyer azlactones
  作者：Philip A. Conway、Kevin Devine、Francesca Paradisi

  DOI：10.1016/j.tet.2009.02.011

  日期：2009.4

  novel and efficient method for synthesising Erlenmeyer azlactones under mild and rapid conditions. The reaction is performed by reacting 2-phenyl-5-oxazolone with an aldehyde in dichloromethane using alumina as a catalyst. The materials react instantly at room temperature, negating the need for high temperatures and long reaction times. We have successfully used this method for both aliphatic, aromatic

  我们最近开发了一种新颖，有效的方法，可在温和快速的条件下合成锥形戊二酸内酯。通过使用氧化铝作为催化剂，使2-苯基-5-恶唑酮与醛在二氯甲烷中反应来进行反应。该材料在室温下可立即反应，从而无需高温和较长的反应时间。我们已经成功地将这种方法用于脂肪族，芳香族和杂芳香族醛类，以中等至高产率合成了以前未制得的锥形戊二烯酮。
• Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity
  作者：Wagdy M. Eldehna、Mohamed A. Abdelrahman、Alessio Nocentini、Silvia Bua、Sara T. Al-Rashood、Ghada S. Hassan、Alessandro Bonardi、Abdulrahman A. Almehizia、Hamad M. Alkahtani、Amal Alharbi、Paola Gratteri、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2019.103102

  日期：2019.9

  In the presented work, we report the synthesis of a series of 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides 7a-fvia the Erlenmeyer-Plöchl reaction. All the prepared imidazolones 7a-f were evaluated as inhibitors of human (h) carbonic anhydrases (CA, EC 4.2.1.1) cytosolic isoforms hCA I and II, as well as transmembrane tumor-associated isoforms hCA IX and XII. All the tested hCA

  在提出的工作中，我们报告了通过Erlenmeyer-Plöchl反应合成一系列基于4-亚苄基-2-苯基-5（4H）-咪唑酮的苯磺酰胺7a-。所有制备的咪唑酮7a-f被评估为人（h）碳酸酐酶（CA，EC 4.2.1.1）胞质同工型hCA I和II以及跨膜肿瘤相关同工型hCA IX和XII的抑制剂。所制备的咪唑啉酮7a-f在以下KIs范围内均以不同程度抑制了所有测试的hCA亚型：hCA I为673.2-8169 nM，hCA II为61.2-592.1 nM，hCA XI为23-155.4 nM，以及21.8- hCA XII为179.6 nM。特别是，咪唑啉酮7a，7e和7f对脱靶胞质（CAs I和II）的肿瘤相关同工型（CAs IX和XII）表现出良好的选择性，选择性指数（SI）在6.2-19.4的范围内和3.3-8，分别。此外，根据US-NCI方案，在对60个癌细胞系的一组剂量（10-5
• Microwave-Assisted Erlenmeyer Synthesis of Azlactones Catalyzed by MgO/Al₂O₃Under Solvent-Free Conditions
  作者：Nader Rostamizadeh、Alireza Khajeh-Amiri、Hassan Moghanian

  DOI：10.1080/15533174.2014.989575

  日期：2016.5.3

  MgO/Al2O3 catalyzes the synthesis of azlactone derivatives from condensation reaction of aldehydes (or ketones) with hippuric acid and acetic anhydride as a dehydrating agent under microwave irradiation. The low toxicity, low cost, ease of handling, and high activity of MgO/Al2O3 make this procedure particularly attractive. Also, this catalyst can be easily recovered by decant and can be reused for

  MgO / Al 2 O 3催化醛（或酮）与作为脱水剂的马尿酸和乙酸酐的缩合反应在微波辐射下的合成内酯衍生物。MgO / Al 2 O 3的低毒性，低成本，易于处理和高活性使该程序特别有吸引力。同样，该催化剂可以容易地通过倾析回收，并且可以连续五次重复用于该缩合反应，而不会显着降低其催化活性。
• An ionic liquid gel: a heterogeneous catalyst for Erlenmeyer–Plochl and Henry reactions
  作者：Megha Jagadale、Altafhusen Naikwade、Rajashri Salunkhe、Mohan Rajmane、Gajanan Rashinkar

  DOI：10.1039/c8nj00367j

  日期：——

  ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully

  通过将1-丁基-3-甲基咪唑鎓氢氧化物（[Bmim] OH）截留在琼脂水溶液中来制备离子液体凝胶。离子液体凝胶的特征在于傅立叶变换红外（FT-IR），傅立叶变换拉曼（FT-Raman）光谱，扫描电子显微镜（SEM），热重分析（TGA）和能量色散X射线分析（EDX）。离子液体凝胶已成功地用作涉及醛，马尿酸和乙酸酐的Erlenmeyer-Plochl反应的多相催化剂，以及室温下醛与硝基甲烷在乙醇中的亨利反应。离子液体凝胶的异质性已通过进行热过滤测试和浸出研究得到证实。此外，