3-氰基-4-甲基香豆素 | 24526-69-0

• 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-氰基-4-甲基香豆素
• 英文名称: 4-methyl-2-oxo-2H-chromene-3-carbonitrile
• 英文别名: 3-cyano-4-methylcoumarin；4-methyl-2-oxochromene-3-carbonitrile
• CAS: 24526-69-0
• 化学式: C₁₁H₇NO₂
• mdl: MFCD00486386
• 分子量: 185.182
• InChiKey: FFBLBFMTKGSSPY-UHFFFAOYSA-N

物化性质

• 熔点：
  192-195 °C (dec.) (lit.)
• 沸点：
  352.2±21.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）
• 稳定性/保质期：

  在常温常压下稳定，避免与氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2932209090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H312,H332

SDS

Name:	3-Cyano-4-methylcoumarin Material Safety Data Sheet
Synonym:
CAS:	24526-69-0

Section 1 - Chemical Product MSDS Name:3-Cyano-4-methylcoumarin Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
24526-69-0	3-Cyano-4-methylcoumarin		unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 24526-69-0: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: light green
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 191 - 193 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: C11H7NO2
Molecular Weight: 185.18

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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 oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 24526-69-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Cyano-4-methylcoumarin - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 24526-69-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 24526-69-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 24526-69-0 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-氰基-4-甲基香豆素 在 哌啶 、 sulfur 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Dimethyl 8-amino-6-oxothiepino[2,3-c]chromene-9,10-dicarboxylate
  参考文献：
  名称：

  Diels-Alder反应中稠合噻吩的反应性：3-氨基噻吩并[3,4：3`，4`]苯并[ b ]吡喃酮的反应性；3-氨基噻吩并[3,4- c ]喹啉和5-氨基-7-取代的噻吩并[3,4- d ]哒嗪酮对贫电子的烯烃和乙炔的反应

  摘要：

  噻吩并[3,4：3`，4`]苯并[ b ]吡喃酮（3b）和噻吩并[3,4- c ]喹啉（3c）是通过使4-甲基香豆素-3-甲腈（9a）与具有元素硫的4-甲基-2-氧-1,2-二氢喹啉-3-腈（9b）类似地，由（10）和元素硫的反应制备噻吩并[3,4：3`，4`]萘并[1,2- b ]吡喃（11）。缩合的噻吩（3b，c）和（11）与各种贫电子烯烃反应生成加成产物，然后消除硫化氢。的反应（图3b，c）中和（11）在回流的二恶烷/乙酸混合物中与丙酸乙酯一起提供缩合的噻吩（24a，c）。（3b，c）和（11）与乙炔二羧酸二甲酯反应的产物的性质取决于所应用的反应条件。因此，（3b，c）和（11）与乙炔二羧酸二甲酯在回流的二恶烷中的反应提供了缩合的噻吩类，同时在250℃下获得了添加和脱硫的产物。噻吩并哒嗪酮（1a，b）与丙烯酸乙酯和富马酸二乙酯反应分别生成噻二氮并ena庚酮（31a-c），化合物（1a

  DOI：

  10.1016/0040-4020(96)00689-8
• 作为产物：
  描述：

  ethyl 2-cyano-2-(2-oxo-2H-chromen-4-yl)acetate 在 氢氧化钾 作用下， 生成 3-氰基-4-甲基香豆素
  参考文献：
  名称：

  Checchi,S. et al., Gazzetta Chimica Italiana, 1969, vol. 99, p. 501 - 513

  摘要：

  DOI：

文献信息

• Gas-phase pyrolysis of 2-heteroaromatic-1-dimethylaminoethylenes: Kinetic and mechanistic study
  作者：Mohamed H. Elnagdi、Nouria A. Al-Awadi、Agith Kumar、Mervat Abdul Khalik

  DOI：10.1002/1098-1071(2001)12:1<47::aid-hc10>3.0.co;2-q

  日期：——

  onitrile (7) (Scheme 1) have been carried out. The rates of gas-phase pyrolytic reactions of compounds 3, 4, 5, and 7 have been measured and found to correspond to unimolecular first-order reactions. Product analyses together with kinetic data were used to outline a feasible pathway for the pyrolytic reactions of the compounds under study. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:47–51, 2001

  4(2'-二甲氨基乙烯基)-2-oxo-2H-benzo[b]pyran-3-carbonitrile (1), 4(2'-二甲氨基乙烯基)-2-oxo-2H-naphtho[1]的气相热解反应,2-b]pyran-3-carbonitrile (2), 1,6-dihydro-4-(2'-dimethylaminoethenyl)-6-oxo-1-phenylpyridazine-3,5-dicarbonitrile (3), 2-cyano- 5-二甲氨基-3-苯基-2,4-戊二烯腈(4), 2-氰基-5-二甲氨基-3-(2-噻吩基)-2,4-戊二烯腈(5), 1,2-二氢-4- (2'-二甲氨基乙烯基)-oxo-quinoline-4-carbonitrile (6), 6-(ethylthio)-4-(2'-dimethylaminoethenyl)-2-phenylpyrimidine-5-carbonitrile
• Palladium‐Catalyzed Regioselective and Diastereoselective <i>C</i> ‐Glycosylation by Allyl‐Allyl Coupling
  作者：Junhao Li、Nan Zheng、Xuelun Duan、Rui Li、Wangze Song

  DOI：10.1002/adsc.202001136

  日期：2021.2.2

  A Pd‐catalyzed C‐glycosylation reaction was developed by allyl‐allyl coupling process using Achmatowicz rearrangement products as donors and methylcoumarins as acceptors under mild conditions. This method featured regio‐ and diastereoselectivities, stereodivergent synthesis of C‐glycosides. The glycosyl donors with controlled stereodiversity and glycosyl acceptors with fluorescent performace further

  在温和条件下，使用Achmatowicz重排产物作为供体，甲基香豆素作为受体，通过烯丙基-烯丙基偶联过程开发了Pd催化的C-糖基化反应。该方法具有区域选择性和非对映选择性，C-糖苷的立体发散合成。具有控制的立体多样性的糖基供体和具有荧光性能的糖基受体进一步强调了该方法。
• New C4- and C1-derivatives of furo[3,4-c]pyridine-3-ones and related compounds: Evidence for site-specific inhibition of the constitutive proteasome and its immunoisoform
  作者：Anna Hovhannisyan、The Hien Pham、Dominique Bouvier、Alexander Piroyan、Laure Dufau、Lixian Qin、Yan Cheng、Gagik Melikyan、Michèle Reboud-Ravaux、Michelle Bouvier-Durand

  DOI：10.1016/j.bmcl.2014.01.072

  日期：2014.3

  furo[3,4-c]pyridine-3-one), 6 model compounds (γ- and δ-lactones) and 20 furo- or thieno[2,3-d]-pyrimidine-4-one related compounds were designed and synthesized. Each compound was assayed for inhibition of CT-L, T-L and PA proteolytic activities of 20S constitutive proteasome (c20S). Most performant compounds were also assayed on 20S immunoproteasome (i20S). Compound 10 with a benzylamino group at C4

  一组18个新的去甲-头孢菌素（1,1-二甲基呋喃[3,4- c ]吡啶-3-一）的C 4和C 1衍生物，6个模型化合物（γ-和δ-内酯）和20个呋喃设计或合成了噻吩并[2,3- d ]-嘧啶-4-one相关化合物。测定每种化合物对20S组成型蛋白酶体（c20S）的CT-L，TL和PA蛋白水解活性的抑制。还可以在20S免疫蛋白酶体（i20S）上分析大多数性能良好的化合物。在呋喃吡啶环的C 4处有苄氨基并在C 1处二甲基化的化合物10是c20S的最有效的PA位点特异性抑制剂（我知道了50每次转化费用600 nM）不会显着抑制i20S PA位点（iPA）。在iPA催化位点的计算机对接分析中，对10个化合物的分析表明，通常在该组成性PA位点（cPA）上没有观察到该化合物及相关位姿。Thieno [2,3- d ]嘧啶-4-酮40具有TL位​​点特异性，在体外对c20S和i20S均具有轻度抑制作用（我知道了50脂蛋白
• Iridium-catalyzed direct asymmetric vinylogous allylic alkylation
  作者：Chang-Yun Shi、Jun-Zhao Xiao、Liang Yin

  DOI：10.1039/c8cc07249c

  日期：——

  alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

  α，β-不饱和内酯（包括香豆素）的催化不对称乙烯基烯丙基烷基化反应具有出色的区域和对映选择性。借助通用的末端烯烃和内酯部分进行产物的转化。通过先进的合成默克中间体向新药物候选者的不对称合成，展示了本方法学的合成应用。
• Silicon-assisted O-heterocyclic synthesis: mild and efficient one-pot syntheses of (E)-3-arylideneflavanones, coumarin-3-carbonitriles/ carboxamides, and benzannulated spiropyran derivatives
  作者：Tarek A. Salama、Mohamed A. Ismail、Abdel-Galil M. Khalil、Saad S. Elmorsy

  DOI：10.3998/ark.5550190.0013.921

  日期：——

  one-pot synthesis of ( E )-benzylideneflavanones, dibenzospiropyrans and coumarin-3-carbonitriles/carboxamides is achieved through tandem aldol-cyclocondensation of o -hydroxyaryl carbonyl compounds with aryl aldehydes or enolisable ketones or through Knoevenagel reaction by the aid of SiCl 4 /EtOH at ambient temperature. Keywords: O-Heterocycles, tetrachlorosilane-ethanol, one-pot synthesis, cyclocondensation

  摘要 通过邻羟基芳基羰基化合物与芳醛或可烯醇化酮的串联醛醇-环缩合反应，实现了一种新的通用且高效的 (E )-亚苄基黄烷酮、二苯并螺吡喃和香豆素-3-甲腈/甲酰胺的一锅合成方法。在环境温度下借助 SiCl 4 /EtOH 进行 Knoevenagel 反应。关键词：O-杂环，四氯硅烷-乙醇，一锅法合成，环缩合 引言 3-亚苄基黄烷酮，称为黄酮类化合物，是合成中的重要组成部分，其骨架在一些天然产物中很常见。1 例如，它们是螺杂环的前体， 2 以及生物学上重要的黄酮。3 此外，许多 3-亚苄基黄烷酮具有抗炎、抗氧化、镇痛和抗菌特性。4 3-亚苄基黄烷酮通常通过黄烷酮与芳香醛的酸或碱催化缩合来合成。

表征谱图