3-乙酰氨基香豆素 | 779-30-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-乙酰氨基香豆素
• 英文名称: 3-acetamidocoumarin
• 英文别名: N-(2-oxo-2H-chromen-3-yl)acetamide；3-Acetamino-cumarin；3-N-acetylaminocoumarin；3-acetylaminocoumarin；N-(2-oxochromen-3-yl)acetamide
• CAS: 779-30-6
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00075556
• 分子量: 203.197
• InChiKey: XJYLCCJIDYSFMB-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C(lit.)
• 沸点：
  482.0±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 安全说明：
  S22,S24/25
• 海关编码：
  2932209090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	3-Acetamidocoumarin Material Safety Data Sheet
Synonym:	None
CAS:	779-30-6

Section 1 - Chemical Product MSDS Name:3-Acetamidocoumarin Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
779-30-6	3-Acetamidocoumarin	>98 %	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:
The toxicological properties of this substance have not been fully investigated.
Inhalation:
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: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
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:
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, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 779-30-6: 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 and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: Solid
Color: Not available.
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 206 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: C11H9NO3
Molecular Weight: 203.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidants.
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# 779-30-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Acetamidocoumarin - 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.
WGK (Water Danger/Protection)
CAS# 779-30-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 779-30-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 779-30-6 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-乙酰氨基香豆素 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-(dimethylamino)-N'-(2-oxochromen-3-yl)-N-phenyliminobenzenecarboximidamide
  参考文献：
  名称：

  Kumar, Atul; Verma, M.; Saxena, A. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 378 - 380

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 3-乙酰氨基香豆素
  参考文献：
  名称：

  Dakin, Journal of Biological Chemistry, 1929, vol. 82, p. 445

  摘要：

  DOI：

文献信息

• Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents
  作者：Sunil Dutt Durgapal、Shubhangi S. Soman

  DOI：10.1080/00397911.2019.1647439

  日期：——

  available for treatment of cancer and diabetes individually, peptide linkage containing proline sulfonamide can be a promising therapy for treatment of both cancer as well as diabetes. Here, we report design and synthesis of novel coumarin-proline sulfonamide derivatives as anticancer and antidiabetic agents. All the synthesized compounds were screened for their anticancer activity against lungs cancer

  摘要 癌症和糖尿病被认为是世界范围内影响人类健康的两大疾病。多种疗法可分别用于治疗癌症和糖尿病，含有脯氨酸磺酰胺的肽键可以成为治疗癌症和糖尿病的有前途的疗法。在这里，我们报告了作为抗癌和抗糖尿病药物的新型香豆素-脯氨酸磺酰胺衍生物的设计和合成。使用 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑鎓溴化物染料 (MTT) 筛选所有合成化合物对肺癌细胞系 (A549) 和乳腺癌细胞系 (MCF7) 的抗癌活性) 测定和使用 DPP-IV 抑制测定的抗糖尿病活性。化合物 16b 对乳腺癌细胞系 (MCF7) 显示出优异的活性，IC50 值为 1.07 µM。所有化合物均表现出中等的 DPP-IV 抑制作用。图形概要
• Benzyne Click Chemistry: Synthesis of Benzotriazoles from Benzynes and Azides
  作者：Feng Shi、Jesse P. Waldo、Yu Chen、Richard C. Larock

  DOI：10.1021/ol800675u

  日期：2008.6.1

  A variety of substituted benzotriazoles have been prepared by the [3 + 2] cycloaddition of azides to benzynes. The reaction scope is quite general, affording a rapid and easy entry to substituted, functionalized benzotriazoles under mild conditions.

  多种取代的苯并三唑已通过叠氮化物与苄的 [3 + 2] 环加成反应制备。反应范围非常广泛，可以在温和的条件下快速轻松地获得取代的、官能化的苯并三唑。
• Copper(<scp>i</scp>)-promoted cycloalkylation–peroxidation of unactivated alkenes via sp³C–H functionalisation
  作者：Arghya Banerjee、Sourav Kumar Santra、Aniket Mishra、Nilufa Khatun、Bhisma K. Patel

  DOI：10.1039/c4ob01962h

  日期：——

  been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide (TBHP) and internal conjugated alkenes possessing electron-withdrawing groups (EWGs). This process installs C–O and C–C bonds via sp3 C–H functionalisation with concomitant generation of two stereocentres. This regioselective radical addition of coumarin system is opposite to that of styrene.

  通过三组分反应，开发了一种由铜（I）促进的环烷基化-过氧化策略，该反应涉及环烷烃，叔丁基氢过氧化物（TBHP）和具有吸电子基团（EWG）的内部共轭烯烃。此过程通过sp 3 C–H功能化安装了C–O和C–C键，并同时生成了两个立体中心。香豆素系统的这种区域选择性自由基加成与苯乙烯相反。
• Design and synthesis of aminocoumarin derivatives as DPP-IV inhibitors and anticancer agents
  作者：Rina Soni、Shubhangi S. Soman

  DOI：10.1016/j.bioorg.2018.05.008

  日期：2018.9

  role in earlier stages of cancer. Here we have reported design, synthesis and applications of aminocoumarin derivatives as DPP-IV inhibitors. Compounds have been synthesized and studied for their DPP-IV inhibition activity. Three compounds have shown moderate inhibition at 100 µM concentration. All compounds were also screened for their anticancer activity against A549 (Lung cancer cell line), MCF-7 (Breast

  DPP-IV“一种月光蛋白”已成为控制2型糖尿病的有前途的途径，并且在癌症的早期阶段起着关键作用。在这里，我们报道了氨基香豆素衍生物作为DPP-IV抑制剂的设计，合成和应用。已合成并研究了化合物对DPP-IV的抑制活性。三种化合物在100 µM浓度下均表现出中等抑制作用。还使用MTT测定法筛选了所有化合物对A549（肺癌细胞系），MCF-7（乳腺癌细胞系）的抗癌活性。这些化合物之一显示出非常好的抗癌活性，对A549细胞系的IC 50值为24±0.1 nM。
• Enantioselective allene/enone photocycloadditions: The use of an inexpensive optically active 1,3-disubstituted allene
  作者：Mary S. Shepard、Erick M. Carreira

  DOI：10.1016/s0040-4020(97)01013-2

  日期：1997.12

  and use of an inexpensive readily prepared optically active 1,3-disubstituted allene that may be utilized for enantioselective intramolecular allene/enone photocycloadditions. In addition, we describe novel substrates for intramolecular [2+2] photocycloadditions which substantially expand the scope of the process to include amino- and thio- tethered allene/enones.

  我们报道了廉价的容易制备的旋光的1，3-二取代的丙二烯的制备和使用，其可以用于对映选择性分子内的丙二烯/烯酮光环加成。此外，我们描述了分子内[2 + 2]光环加成反应的新型底物，该底物大大扩展了该方法的范围，使其包括氨基和硫键联的丙二烯/烯酮。

表征谱图