3-甲基-3-喹诺醇 | 14003-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-甲基-3-喹诺醇
• 中文别名: 3-甲基-2-喹诺醇；3-甲基-2(1H)-喹喔啉；3-甲基-2-羟基喹喔啉
• 英文名称: 3-Methyl-2-oxo-1,2-dihydroquinoxaline
• 英文别名: 3-methylquinoxalin-2(1H)-one；3-methyl-1H-quinoxalin-2-one；2-Hydroxy-3-methylquinoxaline
• CAS: 14003-34-0
• 化学式: C₉H₈N₂O
• mdl: MFCD00006724
• 分子量: 160.175
• InChiKey: BMIMNRPAEPIYDN-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(lit.)
• 沸点：
  286.07°C (rough estimate)
• 密度：
  1.1846 (rough estimate)
• 溶解度：
  DMF：20mg/mL； DMSO：20mg/mL； DMSO:PBS(pH7.2)(1:1)：0.5mg/ml；乙醇：1mg/mL
• LogP：
  1.337 (est)
• 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)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2933990090
• 储存条件：
  请将密闭存放于阴凉干燥的环境中。

SDS

Name:	3-Methyl-2-quinoxalinol Material Safety Data Sheet
Synonym:	2-hydroxy-3-methyl quinoxaline
CAS:	14003-34-0

Section 1 - Chemical Product MSDS Name:3-Methyl-2-quinoxalinol Material Safety Data Sheet
Synonym:2-hydroxy-3-methyl quinoxaline

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14003-34-0	3-methyl-2-quinoxalinol	100.0	237-807-4

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

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.

---

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 immediately.
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 immediately.
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.

---

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:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. 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.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 14003-34-0: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 246.00 - 248.00 deg C
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:
Molecular Formula: C9H8N2O
Molecular Weight: 160.17

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14003-34-0: VD3634500 LD50/LC50:
Not available.
Carcinogenicity:
3-methyl-2-quinoxalinol - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION
Other No information available.

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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# 14003-34-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14003-34-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14003-34-0 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-甲基-3-喹诺醇 在 氢氧化钾 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 14.0h， 生成 5-(3-Methyl-1-methylene-2(1H)-quinoxalinonyl)-2-thio-1,3,4-oxadiazole
  参考文献：
  名称：

  Badr; Mahgoub; Abdel-Latif, Journal of the Indian Chemical Society, 1990, vol. 67, # 3, p. 216 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  cyano-2 (oxo-2' quinoxalinyl-3')-2 acetate d'ethyle 在 HCl 作用下， 以 盐酸 为溶剂， 反应 5.0h， 以20%的产率得到3-甲基-3-喹诺醇
  参考文献：
  名称：

  Essassi, El Mokhtar; Ferfra, Souad; Salem, Moussa, Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 1, p. 47 - 60

  摘要：

  DOI：

文献信息

• Compounds and uses thereof for decreasing activity of hormone-sensitive lipase
  申请人：——

  公开号：US20030166644A1

  公开（公告）日：2003-09-04

  Use of compounds to inhibit hormone-sensitive lipase, pharmaceutical compositions comprising the compounds, methods of treatment employing these compounds and compositions, and novel compounds. The present compounds are inhibitors of hormone-sensitive lipase and may be useful in the treatment and/or prevention of medical disorders where a decreased activity of hormone-sensitive lipase is desirable.

  使用化合物抑制激素敏感性脂肪酶，包括这些化合物的药物组合物，使用这些化合物和组合物的治疗方法，以及新化合物。目前的化合物是激素敏感性脂肪酶的抑制剂，可能在治疗和/或预防需要降低激素敏感性脂肪酶活性的医学疾病中有用。
• Antiplasmodial 2-thiophenoxy-3-trichloromethyl quinoxalines target the apicoplast of Plasmodium falciparum
  作者：Dyhia Amrane、Nicolas Primas、Christophe-Sébastien Arnold、Sébastien Hutter、Béatrice Louis、Julen Sanz-Serrano、Amaya Azqueta、Nadia Amanzougaghene、Shahin Tajeri、Dominique Mazier、Pierre Verhaeghe、Nadine Azas、Cyrille Botté、Patrice Vanelle

  DOI：10.1016/j.ejmech.2021.113722

  日期：2021.11

  and was not genotoxic in the in vitro comet assay. Activity cliffs were observed when the trichloromethyl group was replaced by CH3, CF3 or H, showing that this group played a key role in the antiplasmodial activity. Biological investigations performed to determine the target and mechanism of action of the compound 3k strongly suggest that the apicoplast is the putative target as showed by severe alteration

  鉴定出对疟原虫属（疟原虫的病原体）必不可少的类植物跟腱残骸，即 apicoplast，为具有原始作用机制的新型抗疟药提供了有吸引力的药物靶标。尽管它不是光合作用的，但顶端质体保留了几种对寄生虫必不可少的合成代谢途径。基于先前确定的属于 2-三氯甲基喹唑啉和 3-三氯甲基喹喔啉系列的抗疟原虫命中分子，我们在此报告了 16 种新合成化合物的喹喔啉环第二位的抗疟原虫构效关系 (SAR) 研究。评估它们对多重耐药 K1恶性疟原虫的活性对人肝细胞 HepG2 细胞系的菌株和细胞毒性揭示了一种命中化合物 ( 3k )，其Pf K1 EC 50值为 0.3 μM，HepG2 CC 50值为 56.0 μM（选择性指数 = 175）。此外，hit-compound 3k对 VERO 或 CHO 细胞系没有细胞毒性，在体外彗星试验中也没有基因毒性。当三氯甲基基团被CH 3、CF 3或H取代时，观察到活性悬崖
• [EN] QUINOXALINONE DERIVATIVES AS INSULIN SECRETION STIMULATORS, METHODS FOR OBTAINING THEM AND USE THEREOF FOR THE TREATMENT OF DIABETES<br/>[FR] DÉRIVÉS DE QUINOXALINONE COMME STIMULATEURS DE LA SÉCRÉTION D'INSULINE, LEURS PROCÉDÉS D'OBTENTION ET LEUR UTILISATION POUR LE TRAITEMENT DU DIABÈTE
  申请人：MERCK PATENT GMBH

  公开号：WO2009109258A1

  公开（公告）日：2009-09-11

  The present invention relates to quinoxalinone derivatives of formula (I), wherein R1, R2, R3, R4, R5 and R6 are as defined in claim 1, as insulin secretion stimulators. The invention also relates to the preparation and use of these quinoxalinone derivatives for the prophylaxis and/or treatment of diabetes and pathologies associated. Other preferred compounds are compounds of general formula (I), wherein R1, R2, R3, R4, R5 and R6 can be optionally substituted by one or more groups selected from Z.

  本发明涉及式(I)的喹喔啉酮衍生物，其中R1、R2、R3、R4、R5和R6如权利要求1所定义，作为胰岛素分泌刺激剂。该发明还涉及这些喹喔啉酮衍生物的制备和用途，用于糖尿病和相关病理的预防和/或治疗。其他优选化合物是一般式(I)的化合物，其中R1、R2、R3、R4、R5和R6可以选择性地被来自Z的一个或多个基团取代。
• [EN] TRIAZOLOPYRAZINE DERIVATIVES AND THEIR USE FOR TREATING NEUROLOGICAL AND PSYCHIATRIC DISORDERS<br/>[FR] DÉRIVÉS DE TRIAZOLOPYRAZINE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES NEUROLOGIQUES ET PSYCHIATRIQUES
  申请人：LUNDBECK & CO AS H

  公开号：WO2013034755A1

  公开（公告）日：2013-03-14

  The present invention is directed to triazolopyrazine compounds of Formula (I). Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds as therapeutic agents treating neurological and psychiatric disorders.

  本发明涉及式(I)的三唑吡嗪化合物。该发明的不同方面涉及包含所述化合物的药物组合物以及将该化合物用作治疗神经系统和精神疾病的治疗剂的用途。
• New quinoxaline-based VEGFR-2 inhibitors: design, synthesis, and antiproliferative evaluation with <i>in silico</i> docking, ADMET, toxicity, and DFT studies
  作者：Mohammed M. Alanazi、Hazem Elkady、Nawaf A. Alsaif、Ahmad J. Obaidullah、Hamad M. Alkahtani、Manal M. Alanazi、Madhawi A. Alharbi、Ibrahim H. Eissa、Mohammed A. Dahab

  DOI：10.1039/d1ra05925d

  日期：——

  A new series of 3-methylquinoxaline-based derivatives having the same pharmacophoric features of VEGFR-2 inhibitors have been synthesized and evaluated for their antiproliferative activities against MCF-7 and HepG-2 cells.

  一系列基于3-甲基喹喔啉的衍生物已经合成，并针对MCF-7和HepG-2细胞评估了它们的抗增殖活性。

表征谱图