8-甲基-5-(三氟甲基)喹啉 | 868668-58-0

• 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: 8-甲基-5-(三氟甲基)喹啉
• 英文名称: 8-methyl-5-(trifluoromethyl)quninoline
• 英文别名: 8-methyl-5-(trifluoromethyl)quinoline
• CAS: 868668-58-0
• 化学式: C₁₁H₈F₃N
• 分子量: 211.186
• InChiKey: MHMJNBHDCKQLKY-UHFFFAOYSA-N

物化性质

• 沸点：
  264.5±35.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Methyl-5-(trifluoromethyl)quinoline
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 8-Methyl-5-(trifluoromethyl)quinoline
CAS number: 868668-58-0

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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.

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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.

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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.

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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:

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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.

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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: C11H8F3N
Molecular weight: 211.2

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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, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  8-甲基-5-(三氟甲基)喹啉 、 对甲苯磺酰胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 碘苯二乙酸 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以79%的产率得到4-methyl-N-((5-(trifluoromethyl)quinolin-8-yl)methyl)benzenesulfonamide
  参考文献：
  名称：

  室温下铑 (III) 催化的 8-甲基喹啉与酰胺的 C(sp3)–H 酰胺化

  摘要：

  在这里，我们公开了 8-甲基喹啉的 Rh(III) 催化螯合辅助 C(sp3)-H 活化，它可以使用市售可靠的酰胺作为酰胺实现分子间酰胺化。

  DOI：

  10.1246/cl.150848
• 作为产物：
  描述：

  5-溴-8-甲基喹啉 、 sodium 2,2,2-trifluoroacetate 在 N-甲基吡咯烷酮 、 copper(l) iodide 作用下， 反应 120.0h， 以59%的产率得到8-甲基-5-(三氟甲基)喹啉
  参考文献：
  名称：

  8-甲基喹啉palladacycles：稳定高效的碳-碳键形成催化剂

  摘要：

  环钯，无膦，基于8-甲基喹啉的配合物（2a – j）是芳基碘和溴化物Heck乙烯基化的极佳催化剂，在某些情况下，其营业额大于2500万。催化剂对空气和湿气稳定。

  DOI：

  10.1016/j.tet.2005.06.118

文献信息

• Structure–Activity Relationship for Small Molecule Inhibitors of Nicotinamide<i>N</i>-Methyltransferase
  作者：Harshini Neelakantan、Hua-Yu Wang、Virginia Vance、Jonathan D. Hommel、Stanton F. McHardy、Stanley J. Watowich

  DOI：10.1021/acs.jmedchem.7b00389

  日期：2017.6.22

  biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small molecule inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure–activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogues resulted in the

  烟酰胺N-甲基转移酶（NNMT）是一种基本的胞质生物转化酶，可催化内源性和外源性异源生物的N-甲基化。我们已经确定了具有> 1000倍活性范围的NNMT小分子抑制剂，并为NNMT抑制剂开发了全面的结构-活性关系（SAR）。筛选N-甲基化的喹啉鎓，异喹啉鎓，吡啶鎓和苯并咪唑鎓/苯并噻唑鎓类似物导致鉴定出喹啉鎓是极有希望的具有极低摩尔浓度的支架（IC 50〜1μM）NNMT抑制。基于抑制剂的计算机对接至NNMT底物（烟酰胺）的结合位点在配体-酶相互作用对接得分与实验计算的IC 50值之间产生了稳固的相关性。预测的喹啉类似物的结合方向揭示了与NNMT底物结合位点残基的选择性结合以及驱动蛋白质-配体分子间相互作用和NNMT抑制的基本化学特征。这一新系列的小分子NNMT抑制剂的开发指导了类药物前体抑制剂的未来设计，以治疗以NNMT活性异常为特征的几种代谢和慢性疾病。
• THERAPEUTIC COMPOUNDS
  申请人：Gilead Sciences, Inc.

  公开号：US20130281433A1

  公开（公告）日：2013-10-24

  Compounds disclosed herein including compounds of formula I′: and salts thereof are provided. Pharmaceutical compositions comprising compounds disclosed herein, processes for preparing compounds disclosed herein, intermediates useful for preparing compounds disclosed herein and therapeutic methods for treating an HIV infection using compounds disclosed herein are also provided.

  本文披露的化合物包括公式I′的化合物及其盐。还提供了包含本文披露的化合物的药物组合物、制备本文披露的化合物的方法、用于制备本文披露的化合物的中间体以及使用本文披露的化合物治疗HIV感染的治疗方法。
• Cobalt-catalyzed ring-opening addition of azabenzonorbornadienes <i>via</i> C(sp³)–H bond activation of 8-methylquinoline
  作者：Heng Tan、Ruhima Khan、Dandan Xu、Yongyun Zhou、Xuexin Zhang、Guangrui Shi、Baomin Fan

  DOI：10.1039/d0cc05374k

  日期：——

  The first ring-opening addition of a benzylic C(sp³)–H bond to azabenzonorbornadienes is demonstrated.

  第一个苄基C(sp3)-H键向氮杂苯并[2.2.1]环庚二烯的环开合加成被证明了。
• Rhodium(III)-Catalyzed Oxidative Cross-Coupling of Unreactive C(sp³)–H Bonds with C(sp²)–H Bonds
  作者：Guangying Tan、Jingsong You

  DOI：10.1021/acs.orglett.7b02167

  日期：2017.9.15

  The development of the oxidative cross-coupling of unreactive C(sp3)–H bonds with (hetero)arene C(sp2)–H bonds is considerably appealing, yet conceptually and practically challenging. Here, we disclose the rhodium-catalyzed oxidative heteroarylation of unactivated C(sp3)–H bonds with heteroarene C(sp2)–H bonds. This method provides a step-economic route to β-heteroarylated 2-ethylpyridine derivatives

  未反应的C（sp 3）-H键与（杂）芳烃C（sp 2）-H键的氧化交叉偶联的发展颇具吸引力，但在概念和实践上都具有挑战性。在这里，我们公开了未活化的C（sp 3）-H键与杂芳烃C（sp 2）-H键的铑催化氧化杂芳基化反应。该方法为β-杂芳基化的2-乙基吡啶衍生物的制备提供了分步骤的经济途径，该衍生物具有相对较宽的底物范围，对敏感官能团的高耐受性和高选择性。该方案还可以扩展到8-甲基喹啉衍生物和杂芳烃之间的偶联反应。
• Cobalt(III)-Catalyzed 1,4-Addition of C(sp3)–H Bonds to Maleimides
  作者：Meng Sun、Xiang-Xiang Chen、Jiang-Tao Ren、Jing-Lei Xu、Hu Xie、Wei Sun、Ya-Min Li

  DOI：10.1055/s-0037-1609847

  日期：2018.7

  Quinolines and succinimides play a crucial role in many pharmaceutical and natural products. Although sp2 C–H bond addition reactions have been extensively investigated, Co(III)-catalyzed sp3 C–H bond 1,4-addition reactions are relatively unexplored. In this manuscript, an efficient and atom-economic protocol for alkylation reactions of 8-methylquinolines with maleimides is presented. The reaction exhibits exceptional reactivity, satisfactory yields, excellent chemo- and regioselectivity, and tolerates a variety of functional groups.

  喹啉和琥酰亚胺在许多药物和天然产物中起着关键作用。尽管sp2 C–H键加成反应得到了广泛研究，但Co(III)催化的sp3 C–H键1,4-加成反应相对未被探索。在这篇论文中，提出了一种高效和原子经济的8-甲基喹啉与马来酰亚胺烷基化反应的方案。该反应表现出异常的反应性，令人满意的产率，优异的化学和区域选择性，并且能耐受各种官能团。