2-甲基-喹啉-4-羧酸甲酯 | 55625-40-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-甲基-喹啉-4-羧酸甲酯
• 英文名称: methyl 2-methylquinoline-4-carboxylate
• 英文别名: 2-methyl-quinoline-4-carboxylic acid methyl ester；2-Methyl-chinolin-4-carbonsaeure-methylester；2-Methyl-cinchoninsaeure-methylester；4-Carbomethoxy-2-methylchinolin
• CAS: 55625-40-6
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD01961559
• 分子量: 201.225
• InChiKey: IMGVYHBEXUHRHX-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  314.8±22.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-Methyl-quinoline-4-carboxylic acid methyl ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-Methyl-quinoline-4-carboxylic acid methyl ester
CAS number: 55625-40-6

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C12H11NO2
Molecular weight: 201.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-甲基-喹啉-4-羧酸甲酯 在 盐酸肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 (3-(4-fluorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)(2-methylquinolin-4-yl)methanone
  参考文献：
  名称：

  新型三氟甲基取代的（1 H-吡唑-1-基）（喹啉-4-基）甲酮的合成与细胞毒性

  摘要：

  从靛红和烷基开始聚合合成一系列16种新的多取代的（5-羟基-5-（三氟甲基）-4,5-二氢-1 H-吡唑-1-基）（喹啉-4-基）甲酮描述了（芳基/杂芳基）酮。通过涉及4-烷基（芳基/杂芳基）-4-甲氧基-1,1,1-三氟丁-3-烯-2-酮的[3 + 2]环缩合反应，二杂芳基甲烷酮的收率高达95％。 （通过两步反应）和2-烷基（芳基/杂芳基）-4-碳酰肼（通过三步反应）。随后，通过经典的脱水反应从相应的5-羟基-2-吡唑啉部分获得了代表性的脱水杂环衍生物，得到了相应的（5-（三氟甲基）-1 H-吡唑-1-基）（喹啉-4-基）甲酮（三个实例），产率为69-82％。随后的细胞毒性评估表明，在高浓度（200μM）的人白细胞中，在喹啉2位具有芳香基团且在吡唑3位具有甲基部分的化合物具有明显的细胞毒性。

  DOI：

  10.1016/j.jfluchem.2016.08.012
• 作为产物：
  描述：

  靛红 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 34.0h， 生成 2-甲基-喹啉-4-羧酸甲酯
  参考文献：
  名称：

  新型三氟甲基取代的（1 H-吡唑-1-基）（喹啉-4-基）甲酮的合成与细胞毒性

  摘要：

  从靛红和烷基开始聚合合成一系列16种新的多取代的（5-羟基-5-（三氟甲基）-4,5-二氢-1 H-吡唑-1-基）（喹啉-4-基）甲酮描述了（芳基/杂芳基）酮。通过涉及4-烷基（芳基/杂芳基）-4-甲氧基-1,1,1-三氟丁-3-烯-2-酮的[3 + 2]环缩合反应，二杂芳基甲烷酮的收率高达95％。 （通过两步反应）和2-烷基（芳基/杂芳基）-4-碳酰肼（通过三步反应）。随后，通过经典的脱水反应从相应的5-羟基-2-吡唑啉部分获得了代表性的脱水杂环衍生物，得到了相应的（5-（三氟甲基）-1 H-吡唑-1-基）（喹啉-4-基）甲酮（三个实例），产率为69-82％。随后的细胞毒性评估表明，在高浓度（200μM）的人白细胞中，在喹啉2位具有芳香基团且在吡唑3位具有甲基部分的化合物具有明显的细胞毒性。

  DOI：

  10.1016/j.jfluchem.2016.08.012

文献信息

• Studies on the N-oxides of .PI.-deficient N-heteroaromatics. XXXIV. A novel synthesis of substituted indoles by photochemical ring contraction of 3,1-benzoxazepines.
  作者：CHIKARA KANEKO、HARUE FUJII、SHINJI KAWAI、ATSUSHI YAMAMOTO、KAZUHIKO HASHIBA、TOSHIHIKO KIMATA、REIKO HAYASHI、MASANORI SOMEI

  DOI：10.1248/cpb.28.1157

  日期：——

  A novel photochemical ring-contraction reaction of 5-unsubstituted 3, 1-benzoxazepines and their 5-halogeno or carboxyl derivatives to yield 3-formylindoles in an aprotic solvent is reported. This ring contraction was successfully extended to oxazepines having an alkoxycarbonyl function at the 5-position to give the indoles having this function at the 3-position. Though most of the oxazepines underwent the ring-contraction reaction only on irradiation at 254 nm, 5-carboxy derivatives or their esters afforded the ring-contraction products even at ≥ 300 nm. The intermediacy of 3H-indole species in these photochemical ring-contraction reactions was demonstrated by the isolation of methyl 3-acetyl-2-phenyl-3H-indole-3-carboxylate during the photolysis of methyl 4-methyl-2-phenyl-3, 1-benzoxazepine-5-carboxylate. It was found that this 3H-indole afforded methyl 6-and 4-acetyl-2-phenyl-indole-3-carboxylates upon further irradiation. The mechanism of this acetyl migration is discussed based on the result of the photochemical acetyl migration of methyl 1-acetyl-2-phenylindole-3-carboxylate.

  报道了一种在非质子溶剂中，5-未取代的3,1-苯并噁嗪和其5-卤素或羧基衍生物发生的新型光化学环收缩反应，生成3-甲酰基吲哚。这种环收缩反应成功扩展到5-位具有烷氧羰基功能的噁嗪，生成3-位具有该功能的吲哚。尽管大多数噁嗪仅在254 nm波长下发生环收缩反应，5-羧基衍生物或其酯甚至在≥ 300 nm波长下也能生成环收缩产物。通过在4-甲基-2-苯基-3,1-苯并噁嗪-5-羧酸甲酯的光解过程中分离出甲基3-乙酰基-2-苯基-3H-吲哚-3-羧酸酯，证明了这些光化学环收缩反应中3H-吲哚的中间体性质。发现进一步的辐照使这种3H-吲哚生成甲基6-和4-乙酰基-2-苯基-吲哚-3-羧酸酯。根据甲基1-乙酰基-2-苯基吲哚-3-羧酸酯的光化学乙酰迁移结果，讨论了这种乙酰迁移的机制。
• 喹啉取代查尔酮类化合物、其制备方法及用途
  申请人：中国药科大学

  公开号：CN109467549B

  公开（公告）日：2021-02-09

  本发明公开了一种喹啉取代查尔酮类新化合物、其可药用的盐，及其制备方法；还公开了一种药用组合物，其包含治疗有效量的喹啉取代查尔酮类新化合物和/或其可药用的盐，以及药学上可接收的载体。本发明还公开了一种微管蛋白抑制剂，其包含上述喹啉取代查尔酮类新化合物和/或其可药用的盐。本发明还公开上述喹啉取代查尔酮类新化合物和/或其可药用的盐在制备治疗包括但不限于结肠癌、白血病、肝癌、乳腺癌等疾病的药物中的应用。本申请化合物显示出优异的抗肿瘤活性，其代谢性质更为稳定，具有更好的成药性前景。
• Antiinflammation agents
  申请人：Browner F. Michelle

  公开号：US20070135464A1

  公开（公告）日：2007-06-14

  Compounds, compositions and methods that are useful in the treatment of inflammatory, immunoregulatory, metabolic and cell proliferative conditions or diseases are provided herein. In particular, the invention provides compounds which modulate the expression and/or function of proteins involved in inflammation, metabolism and cell proliferation. The subject compounds contain fused carbocyclic or heterocyclic rings.

  本文提供了在治疗炎症、免疫调节、代谢和细胞增殖状况或疾病中有用的化合物、组合物和方法。特别地，本发明提供了调节参与炎症、代谢和细胞增殖的蛋白质表达和/或功能的化合物。所述化合物包含融合的碳环或杂环环。
• Meyer,H., Monatshefte fur Chemie, 1907, vol. 28, p. 38
  作者：Meyer,H.

  DOI：——

  日期：——
• Untersuchungen in der Reihe der Isochinoline. VI. Teil
  作者：B. B. Dey、B. S. Alamela

  DOI：10.1002/ardp.19422800702

  日期：——