3-苯甲酰苯并[f]香豆素 | 4852-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 3-苯甲酰苯并[f]香豆素
• 英文名称: 2-benzoyl-3H-benzo[f]chromen-3-one
• 英文别名: 3-benzoyl-5,6-benzocoumarin；2-benzoylbenzo[f]chromen-3-one
• CAS: 4852-81-7
• 化学式: C₂₀H₁₂O₃
• mdl: MFCD00051371
• 分子量: 300.313
• InChiKey: JPPGTVYDWHSNLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  215 °C
• 沸点：
  401.54°C (rough estimate)
• 密度：
  1.2200

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

SDS

Name:	3-Benzoylbenzo[f]coumarin Material Safety Data Sheet
Synonym:	None
CAS:	4852-81-7

Section 1 - Chemical Product MSDS Name:3-Benzoylbenzo[f]coumarin Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4852-81-7	3-Benzoylbenzo[f]coumarin	ca. 100	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.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
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:
Antidote: None reported.

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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 water, dry chemical, chemical foam, or alcohol-resistant 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. 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. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. 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# 4852-81-7: 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: Powder
Color: yellow
Odor: none reported
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: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.2200g/cm3
Molecular Formula: C20H12O3
Molecular Weight: 300.30

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4852-81-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Benzoylbenzo[f]coumarin - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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# 4852-81-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4852-81-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4852-81-7 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-苯甲酰苯并[f]香豆素 在 吡啶 、 sodium tetrahydroborate 作用下， 反应 5.0h， 以50%的产率得到3-benzoyl-5,6-benzo-3,4-dihydrocoumarin
  参考文献：
  名称：

  氧化脱羧次碘酸铵催化二氢苯并呋喃合成

  摘要：

  在氧化条件下催化使用季铵碘化物可以通过原位形成的次碘酸铵物质促进的脱羧氧化环醚化序列将容易获得的 β-酮内酯直接转化为二氢苯并呋喃。

  DOI：

  10.1039/d2ob00463a
• 作为产物：
  描述：

  2-萘酚 在 哌啶 、 四氯化钛 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-苯甲酰苯并[f]香豆素
  参考文献：
  名称：

  Development of Pyrazolone and Isoxazol-5-one Cambinol Analogues as Sirtuin Inhibitors

  摘要：

  Sirtuins are a family of NAD+-dependent protein deacetylases that play critical roles in epigenetic regulation, stress responses, and cellular aging in eukaryotic cells. In an effort to identify small molecule inhibitors of sirtuins for potential use as chemotherapeutics as well as tools to modulate sirtuin activity, we previously identified a nonselective sirtuin inhibitor called cambinol (IC50 approximate to 50 mu M for SIRT1 and SIRT2) with in vitro and in vivo antilymphoma activity. In the current study, we used saturation transfer difference (STD) NMR experiments with recombinant SIRT1 and 20 to map parts of the inhibitor that interacted with the protein. Our ongoing efforts to optimize cambinol analogues for potency and selectivity have resulted in the identification of isoform selective analogues: 17 with >7.8-fold selectivity for SIRT1, 24 with >15.4-fold selectivity for SIRT2, and 8 with 6.8- and 5.3-fold selectivity for SIRT3 versus SIRT1 and SIRT2, respectively. In vitro cytotoxicity studies with these compounds as well as EX527, a potent and selective SIRT1 inhibitor, suggest that antilymphoma activity of this compound class. may be predominantly due to SIRT2 inhibition.

  DOI：

  10.1021/jm4018064

文献信息

• Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
  作者：Daniela Secci、Simone Carradori、Adriana Bolasco、Paola Chimenti、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.ejmech.2011.07.017

  日期：2011.10

  Several 3-carbonyl (1–26), 3-acyl (27–52), and 3-carboxyhydrazido (53–58) coumarins have been synthesized in high yields (72–99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl

  几个-3-羰基（1 - 26），3-酰基（27 - 52），和3- carboxyhydrazido（53 - 58）香豆素已经以高收率（72-99％）合成并测试在体外对它们的人类单胺氧化酶A和B（hMAO-A和hMAO-B）的抑制活性。评价了香豆素核上的不同取代基对生物活性和同工型选择性的影响。对于使用IC 50获得高效且选择性的hMAO-B抑制剂而言，在3-乙酯香豆素环的C7位取代或在C3引入肼基取代基很重要。值在纳摩尔范围内。一些衍生物也进行了稳定性测试，在体外没有化​​学裂解。
• Tunable Phosphine-Triggered Cascade Reactions of MBH Derivatives and 3-Acyl-2<i>H</i>-chromen-2-ones: Highly Selective Synthesis of Diverse Chromenones
  作者：Wei Yuan、Hu-Fei Zheng、Zhi-Hua Yu、Zi-Long Tang、De-Qing Shi

  DOI：10.1002/ejoc.201301358

  日期：2014.1

  Diverse chromenones were synthesized through tunable phosphine-mediated cascade reactions between 3-acyl-2H-chromen-2-ones and Morita–Baylis–Hillman (MBH) derivatives. With different phosphine loadings and reaction temperatures, MBH derivatives act either as C1 or C3 synthons for the construction of potential biologically active 3-dihydrofuran-fused chromen-2-ones, 4-allyl-3-acyl-chromen-2-ones, or

  通过可调膦介导的 3-acyl-2H-chromen-2-ones 和 Morita-Baylis-Hillman (MBH) 衍生物之间的级联反应合成了多种色酮。在不同的膦负载量和反应温度下，MBH 衍生物充当 C1 或 C3 合成子，用于构建潜在的生物活性 3-二氢呋喃稠合 chromen-2-ones、4-allyl-3-acyl-chromen-2-ones，或6H-benzo[c]chromen-6-ones。该方法具有条件温和、后处理简单、底物适用范围广等优点，可有效合成多种色酮衍生物。
• ROS Inhibitory Activity and Cytotoxicity Evaluation of Benzoyl, Acetyl, Alkyl Ester, and Sulfonate Ester Substituted Coumarin Derivatives
  作者：Uzma Salar、Khalid M. Khan、Almas Jabeen、Aisha Faheem、Farwa Naqvi、Shakil Ahmed、Erum Iqbal、Farman Ali、Kanwal、Shahnaz Perveen

  DOI：10.2174/1573406415666190826153001

  日期：2020.11.23

  Limited SAR study revealed that the hydroxy-substituted compound showed better ROS inhibition potential in case of 3-benzoyl and 3-ethylester coumarin derivatives. Whereas, chloro substitution was found to be important in case of 3-acetyl coumarin derivatives. Similarly, in case of sulfonate ester, chloro, and nitro groups especially at positions -4 and -3 of ring "R" played vital role in ROS inhibition

  背景许多非甾体抗炎药(NSAID)，包括阿司匹林、消炎痛、布洛芬、氟芬那酸和保泰松在临床上用于治疗炎性疾病。这些非甾体抗炎药与严重的副作用有关，例如胃溃疡、肾毒性和出血。因此，确定有效和安全的炎症性疾病治疗方法仍然是药物化学家非常感兴趣的。方法 使用鲁米诺增强化学发光技术筛选了一系列不同取代的苯甲酰基、乙酰基、烷基酯和磺酸酯取代的香豆素 1-64 对活性氧的抑制作用，活性氧是由酵母聚糖激活的全血吞噬细胞产生的。结果 在所有测试化合物中，8 (IC50 = 65.0 ± 3.1 μM)、24 (IC50 = 41.8 ± 1.5 μM)、26 (IC50 = 10.6 ± 2.8 μM)、28 (IC50 = 20。9 ± 1.5 μM)和 41 (IC50 = 4.6 ± 0.3 μM) 与标准抗炎药布洛芬 (IC50 = 54.3 ± 1.9 μM) 相比显示出良好的抗炎潜力。具体而言，化合物
• Reactions of zinc enolates derived from 1-aryl-2,2-di-bromoalkanones with 2-acyl-3H-benzo[f]chromen-3-ones, 6-bromo-2-oxochromene-3-carboxamides, and 3-oxo-3H-benzo-[f]chromene-2-carboxamides
  作者：V. V. Shchepin、M. M. Kalyuzhnyi、P. S. Silaichev、N. Yu. Russkikh、R. V. Shchepin、M. A. Ezhikova、M. I. Kodess

  DOI：10.1007/s11178-005-0019-z

  日期：2004.9

  Zinc enolates derived from substituted 1-aryl-2,2-dibromoalkanones reacted with 2-acyl-3H-benzo-[f]chromen-3-ones to give 1-alkyl-1-aroyl-1a-acyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-ones which were formed as a single stereoisomer. Reactions of the same zinc enolates with 6-bromo-2-oxo-chromene-3-carboxamides (piperidides and morpholides) afforded 1-aroyl-6-bromo-1-alkyl-1a-piperidino-(morpholino)carbonyl-1a,7b-dihydrocyclopropa[c]chromen-2-ones with high stereoselectivity. Likewise, 1-benzoyl-1-methyl-1a-morpholinocarbonyl-1a, 9c-dihydro-1H-3-oxacyclopropa[c]phenanthren-2-one was obtained by reac-tion with 3-oxo-3H-benzo[f]chromene-2-carboxylic acid morpholide.

  由取代的1-芳基-2,2-二溴烷酮衍生的锌醇盐与2-酰基-3H-苯并[f]色烯-3-酮反应，生成1-烷基-1-酰基-1a-酰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮，以单一立体异构体的形式形成。相同的锌醇盐与6-溴-2-氧-色烯-3-氨基酸酯（哌啶类和吗啉类）反应，得到1-酰基-6-溴-1-烷基-1a-哌啶（吗啉）羰基-1a, 7b-二氢环丙烷[c]色烯-2-酮，具有高立体选择性。同样，1-苯甲酰-1-甲基-1a-吗啉羰基-1a, 9c-二氢-1H-3-氧杂环丙烷[c]菲-2-酮是通过与3-氧-3H-苯并[f]色烯-2-羧酸吗啉的反应获得的。
• Analytical studies on isoxazoles. II. A new fluorimetric determination of 5-phenyl-3-isoxazolecarboxylic acid and its application to the determination of perisoxal in plasma.
  作者：TSUNEJI UMEDA、HIROKO IMANISHI、EIZO HIRAI

  DOI：10.1248/cpb.28.3507

  日期：——

  A novel fluorimetric method is described for the determination of 5-phenyl-3-isoxazolecarboxylic acid (PIA) by using 2-hydroxy-1-naphthalenecarbaldehyde (HNA) ; this method was utilized to provide a specific and sensitive assay procedure for perisoxal in plasma. The developed fluorophore was 3-benzoyl-5, 6-benzocoumarin (BBC), obtained by Knoevenagel condensation of benzoylacetonitrile with HNA, followed by cyclization. Linear relationships between fluorescence intensity and concentration existed over the concentration range of 35-350 ng/ml of PIA and 70-700 ng/ml of perisoxal in plasma. This method is 70 times more sensitive than the colorimetric method reported previously.

  本文描述了一种新颖的荧光测定方法，用于通过2-羟基-1-萘甲醛（HNA）测定5-苯基-3-异恶唑羧酸（PIA）；该方法可用于提供一种特异性和灵敏度高的血浆过氧草酸的测定程序。所开发的荧光基团为3-苯甲酰-5,6-苯并香豆素（BBC），通过苯甲酰乙腈与HNA的Knoevenagel缩合反应后环化得到。在35-350 ng/ml的PIA浓度范围和70-700 ng/ml的血浆过氧草酸中，荧光强度与浓度之间存在线性关系。该方法的灵敏度比之前报道的比色法高70倍。