3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one | 28081-14-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one
• CAS: 28081-14-3
• 化学式: C₁₇H₁₅FO₃
• mdl: MFCD04051791
• 分子量: 286.303
• InChiKey: MWFPOMHEKFNGLA-UHFFFAOYSA-N

物化性质

• 熔点：
  90-93 °C(lit.)
• 沸点：
  92-94 °C
• 密度：
  1.2105 (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)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090
• 安全说明：
  S26,S37/39
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	3 4-Dimethoxy-4 -fluorochalcone 98% Material Safety Data Sheet
Synonym:	1-(4-Fluorophenyl)-3-(3,4-dimethoxyphenyl)-2-propenone
CAS:	28081-14-3

Section 1 - Chemical Product MSDS Name:3 4-Dimethoxy-4 -fluorochalcone 98% Material Safety Data Sheet
Synonym:1-(4-Fluorophenyl)-3-(3,4-dimethoxyphenyl)-2-propenone

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
28081-14-3	3,4-Dimethoxy-4'-fluorochalcone	98	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
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. May be harmful if swallowed.
Inhalation:
Causes 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, immediately flush skin with plenty of water.
Remove contaminated clothing and shoes. Get medical aid. 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:
If inhaled, remove to fresh air. 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. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical 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. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with skin and eyes. Avoid breathing dust.
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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 28081-14-3: 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: pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 92 - 94 deg C
Freezing/Melting Point: 88 - 93 deg C
Autoignition Temperature: Not available.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C17H15FO3
Molecular Weight: 286.30

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 28081-14-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dimethoxy-4'-fluorochalcone - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 28081-14-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 28081-14-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 28081-14-3 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：

  3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one 在 氯磺酸 、 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (4-bromo-2-ethyl-6,7-dimethoxy-1,1-dioxido-3,4-dihydro-2H-benzo[e][1,2]thiazin-3-yl)(4-fluorophenyl)methanone
  参考文献：
  名称：

  1,2-苯并噻嗪衍生物的合成及抗菌活性

  摘要：

  许多 1,2-苯并噻嗪已在三步法中合成。九个带有甲基、氟、氯和溴取代基的查耳酮 1-9 用氯磺酸进行氯磺化，生成查耳酮磺酰氯 10-18。这些通过与冰醋酸中的溴反应转化为二溴化合物 19-27。化合物 19-27 与氨、甲胺、乙胺、苯胺和苄胺反应生成 45 个 1,2-苯并噻嗪 28-72 库。使用肉汤微量稀释技术对两种革兰氏阳性菌（枯草芽孢杆菌和金黄色葡萄球菌）和两种革兰氏阴性菌（变形杆菌和鼠伤寒沙门氏菌）评估化合物 28-72 的抗菌活性。结果表明，没有一种化合物对革兰氏阴性细菌 P. vulgaris 和 S. typhimurium 显示出任何活性；然而，化合物 31、33、38、43、45、50、53、55、58、60、63 和 68 显示出对革兰氏阳性细菌枯草芽孢杆菌和金黄色葡萄球菌的活性。最低抑菌浓度 (MIC) 和最低杀菌浓度 (MBC) 的范围为 25–600 µg/mL，但部分

  DOI：

  10.3390/molecules21070861
• 作为产物：
  描述：

  acetyl-p-fluorophenyltriphenylarsonium bromide 在 sodium ethanolate 作用下， 以 苯 为溶剂， 反应 80.0h， 生成 3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Bansal, Raj K.; Bhagchandani, Gope, Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 1, p. 49 - 54

  摘要：

  DOI：

文献信息

• A Novel Series of 3,4-Disubstituted Dihydropyrazoles: Synthesis and Evaluation for MAO Enzyme Inhibition
  作者：Maria Cristina Cardia、Maria Luisa Sanna、Rita Meleddu、Simona Distinto、Matilde Yañez、Dolores Viña、Manuel Lamela、Elias Maccioni

  DOI：10.1002/jhet.1072

  日期：2013.2

  In this study, the authors have designed and synthesized a novel series of 3-acyl-4-aryl-4,5-dihydropyrazoles, with the aim to obtain new potential scaffolds for the inhibition of both isoforms of monoamine oxidase (MAO) enzyme. The synthetic pathway to these compounds includes as a key step the 1,3-dipolar cycloaddition reaction of diazomethane with a chalcone. All the compounds were fully characterized

  在这项研究中，作者设计并合成了一系列新的3-酰基-4-芳基-4,5-二氢吡唑类化合物，目的是获得新的抑制单胺氧化酶（MAO）两种同工型的潜在支架。这些化合物的合成途径包括关键步骤：重氮甲烷与1,3-偶极甲烷的1,3-偶极环加成反应。查尔酮。所有化合物均通过光谱和分析数据充分表征，并显示出对MAO A的特异性抑制作用。
• Synthesis and Antibacterial Activity of Benzo[4,5]isothiazolo[2,3-a]pyrazine-6,6-dioxide Derivatives
  作者：Jatinder Bassin、Michelle Botha、Rajesh Garikipati、Madhu Goyal、Lee Martin、Amit Shah

  DOI：10.3390/molecules22111889

  日期：——

  Using a routine procedure, a number of derivatives of the benzo[4,5]isothiazolo[2,3-a]pyrazine-6,6-dioxide ring system have been synthesized from readily available starting materials. A series of chalcones were synthesized, which were subsequently reacted with chlorosulfonic acid to generate chalcone sulfonyl chlorides. The chalcone sulfonyl chlorides were then treated with bromine to generate dibromo

  使用常规程序，苯并[4,5]异噻唑并[2,3-a]吡嗪-6,6-二氧化物环系统的许多衍生物已经从容易获得的起始材料合成。合成了一系列查耳酮，随后与氯磺酸反应生成查耳酮磺酰氯。然后用溴处理查耳酮磺酰氯以生成二溴查耳酮磺酰氯。这些随后在沸腾的乙醇中与 1,2-二氨基丙烷和 2-甲基-1,2-二氨基丙烷反应，分别生成化合物 2-10 和 11-19，产率为 12-80%。产物通过光谱分析表征，化合物 11 的最终结构通过 X 射线晶体学确定。筛选合成的化合物对枯草芽孢杆菌的潜在抗菌特性，
• Synthesis and bioactivities of pyrazoline benzensulfonamides as carbonic anhydrase and acetylcholinesterase inhibitors with low cytotoxicity
  作者：Dilan Ozmen Ozgun、Halise Inci Gul、Cem Yamali、Hiroshi Sakagami、Ilhami Gulcin、Murat Sukuroglu、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.12.028

  日期：2019.3

  and 200 µM towards OSCC malign cell lines. Their tumor selectivities were also calculated with two ways. Compound's selectivities towards cancer cell line were found generally low, except compounds bearing 3,4-dimethoxyphenyl 14 (TS1 = 1.3, TS2 = 1.4) and 10 (TS2 = 1.4). All sulfonamide derivatives studied here can be considered as good candidates to develop novel CAs or AChE inhibitor candidates based

  合成了4-（3-取代的苯基-5-聚甲氧基苯基-4,5-二氢-1H-吡唑-1-基）苯磺酰胺（9-16），并通过1H NMR，13C NMR和HRMS阐明了它们的化学结构。通过hibrit分子方法，所设计的化合物在单个分子中包括吡唑啉和磺酰胺药效团，这是药物化学中有用的技术，可用于设计对所需的几种生物活性具有有效活性的新化合物。评估了磺酰胺类对人CA同工酶（hCA IandhCA II）和乙酰胆碱酯酶（AChE）酶的抑制能力，并研究了它们对口腔鳞癌（OSCC）细胞系（Ca9-22，HSC-2，HSC- 3，以及HSC-4）和非肿瘤细胞（HGF，HPLF和HPC）。磺酰胺衍生物可抑制胞质hCA I和hCA II同工酶（9-16），Ki值分别在27.9±3.2-74.3±28.9 nM和27.4±1.4-54.5±11.6 nM之间。AChE酶被磺酰胺衍生物强烈抑制，Ki值在37.7±14.4-89
• Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
  作者：Neha Upadhyay、Kalpana Tilekar、Fulvio Loiodice、Natalia Yu. Anisimova、Tatiana S. Spirina、Darina V. Sokolova、Galina B. Smirnova、Jun-yong Choe、Franz-Josef Meyer-Almes、Vadim S. Pokrovsky、Antonio Lavecchia、CS Ramaa

  DOI：10.1016/j.bioorg.2020.104527

  日期：2021.2

  antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases

  为了寻找新的、更安全的抗癌药物，采用了两种特殊支架（即二芳基吡唑啉和咪唑烷-2,4-二酮（乙内酰脲））的结构引导药效团杂交策略，产生了一系列新型化合物（H1-H22 ））。在此，我们最近报道的抗肿瘤杂合体的“吡咯烷-2,5-二酮”部分的生物等排替换，该杂合体结合了二芳基吡唑啉和吡咯烷-2,5-二酮支架，并具有“咪唑啉-2,4-二酮”部分。 。完整的生物学研究揭示了所有类似物中最有效的类似物，即化合物H13，其在结肠癌细胞和乳腺癌细胞中的效力比相应的吡咯烷-2,5-二酮至少高10倍。体外研究表明，半胱天冬酶被激活，细胞周期 G0/G1 期停滞，抗凋亡蛋白 (Bcl-2) 表达减少，DNA 损伤增加。对 HT-29（人结直肠腺癌）动物异种移植模型的体内测定揭示了显着的抗肿瘤功效以及口服生物利用度，在 50 mg/kg 剂量下，最大 TGI 为 36%（腹腔注射）和 44%（口服）。这些发现证实了杂交吡唑啉和咪唑烷-2
• An efficient and direct synthesis of 2-thiopyridines<i>via</i>microwave-assisted three-component reaction
  作者：Xing-Han Wang、Xu-Dong Cao、Shu-Jiang Tu、Xiao-Hong Zhang、Wen-Juan Hao、Shu Yan、Shan-Shan Wu、Zheng-Guo Han、Feng Shi

  DOI：10.1002/jhet.161

  日期：2009.9

  A series of 2-p-tolylthiopyridine derivatives was directly synthesized via three-component reactions of chalcones, malononitrile, and 4-methylbenzenethiol catalyzed by Et3N in DMF under microwave irradiation. It is an efficient and promising synthetic strategy to construct 2-thiopyridine skeleton with the advantage of short time, excellent yield, and convenient operation. J. Heterocyclic Chem., (2009)

  通过查耳酮的三组分反应直接合成了一系列2- p-甲苯基硫代吡啶衍生物，丙二腈，并Et 3 N在DMF中微波辐射下催化的4-甲基苯硫醇。构建2-硫代吡啶骨架具有时间短，收率高，操作方便等优点，是一种有效而有前景的合成策略。J.杂环化​​学，（2009）。