4-溴-6-甲氧基-2-(三氟甲基)喹啉 | 18706-38-2

• 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: 4-溴-6-甲氧基-2-(三氟甲基)喹啉
• 英文名称: 2-trifluoromethyl-4-bromo-6-methoxyquinoline
• 英文别名: 4-bromo-6-methoxy-2-trifluoromethyl-quinoline；6-Methoxy-4-brom-2-trifluormethyl-chinolin；4-Bromo-6-methoxy-2-(trifluoromethyl)quinoline
• CAS: 18706-38-2
• 化学式: C₁₁H₇BrF₃NO
• 分子量: 306.082
• InChiKey: IVMJQGFGIGPEPH-UHFFFAOYSA-N

物化性质

• 沸点：
  311.3±37.0 °C(Predicted)
• 密度：
  1.606±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Bromo-6-methoxy-2-(trifluoromethyl)quinoline
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-6-methoxy-2-(trifluoromethyl)quinoline
CAS number: 18706-38-2

---

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: C11H7BrF3NO
Molecular weight: 306.1

---

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, hydrogen bromide.

---

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：

  4-溴-6-甲氧基-2-(三氟甲基)喹啉 在 四氢吡咯 、 甲醇 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 nickel(II) chloride hexahydrate 、 碳酸氢钠 、 甲基磺酰氯 、 间氯过氧苯甲酸 、 苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 异丙醇 、 乙腈 为溶剂， 反应 26.0h， 生成 ethyl (1'S,3R,4'R,6'S,7'Z,14'S)-9-methoxy-14'-[(2-methylpropan-2-yl)oxycarbonylamino]-2',15'-dioxo-5-(trifluoromethyl)spiro[1,2-dihydropyrano[2,3-c]quinoline-3,18'-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene]-4'-carboxylate
  参考文献：
  名称：

  MK-8831，一种新型螺脯氨酸大环化合物作为泛基因型HCV-NS3 / 4a蛋白酶抑制剂的发现

  摘要：

  我们一直专注于鉴定与MK-5172（我们的Ns3 / 4a蛋白酶抑制剂，目前正在监管审查中）在结构上不同的下一代抑制剂，该抑制剂将实现具有可接受的安全性和药代动力学特征的优异的泛型活性。这些努力导致发现了一种新型的HCV NS3 / 4a蛋白酶抑制剂，该抑制剂具有独特的螺环-脯氨酸结构基序。设计策略包括基于分子建模的方法，以及对该系列的优化工作，以获得具有良好口服剂量暴露的泛基因型覆盖率。这项工作的关键要素之一是P2喹啉基团的螺环化，它刚性化并限制了结合构象，从而提供了一个新的核心。该小组的第二个重点还在于提高针对基因型3a和基因型1b关键突变体的活性。结构化学与分子建模的合理应用指导了结构与活性关系的设计和优化，从而鉴定出具有优良泛基因型活性和安全性的临床候选药物MK-8831。

  DOI：

  10.1021/acsmedchemlett.5b00425

文献信息

• [EN] HCV NS3 PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉASE NS3 DU VHC
  申请人：MERCK SHARP & DOHME

  公开号：WO2014025736A1

  公开（公告）日：2014-02-13

  The present invention relates to hepatitis C virus (HCV) NS3 protease inhibitors containing a spirocyclic moeity, uses of such compounds, and synthesis of such compounds.

  这项发明涉及含有螺环结构基团的丙型肝炎病毒（HCV）NS3蛋白酶抑制剂，以及这类化合物的用途和合成。
• HCV NS3 PROTEASE INHIBITORS
  申请人：BARA Thomas

  公开号：US20140057836A1

  公开（公告）日：2014-02-27

  The present invention relates to hepatitis C virus (HCV) NS3 protease inhibitors containing a spirocyclic moeity, uses of such compounds, and synthesis of such compounds.

  本发明涉及含有螺环结构的丙肝病毒（HCV）NS3蛋白酶抑制剂，以及这些化合物的用途和合成方法。
• US8987195B2
  申请人：——

  公开号：US8987195B2

  公开（公告）日：2015-03-24
• Discovery of MK-8831, A Novel Spiro-Proline Macrocycle as a Pan-Genotypic HCV-NS3/4a Protease Inhibitor
  作者：Santhosh F. Neelamkavil、Sony Agrawal、Thomas Bara、Chad Bennett、Sathesh Bhat、Dipshikha Biswas、Linda Brockunier、Nicole Buist、Duane Burnette、Mark Cartwright、Samuel Chackalamannil、Robert Chase、Mariappan Chelliah、Austin Chen、Martin Clasby、Vincent J. Colandrea、Ian W. Davies、Keith Eagen、Zhuyan Guo、Yongxin Han、John Howe、Charles Jayne、Hubert Josien、Stacia Kargman、Karen Marcantonio、Shouwu Miao、Randy Miller、Andrew Nolting、Patrick Pinto、Murali Rajagopalan、Rebecca T. Ruck、Unmesh Shah、Aileen Soriano、Donald Sperbeck、Francisco Velazquez、Jin Wu、Yan Xia、Srikanth Venkatraman

  DOI：10.1021/acsmedchemlett.5b00425

  日期：2016.1.14

  different next generation inhibitor to MK-5172 (our Ns3/4a protease inhibitor currently under regulatory review), which would achieve superior pangenotypic activity with acceptable safety and pharmacokinetic profile. These efforts have led to the discovery of a novel class of HCV NS3/4a protease inhibitors containing a unique spirocyclic-proline structural motif. The design strategy involved a molecular-modeling

  我们一直专注于鉴定与MK-5172（我们的Ns3 / 4a蛋白酶抑制剂，目前正在监管审查中）在结构上不同的下一代抑制剂，该抑制剂将实现具有可接受的安全性和药代动力学特征的优异的泛型活性。这些努力导致发现了一种新型的HCV NS3 / 4a蛋白酶抑制剂，该抑制剂具有独特的螺环-脯氨酸结构基序。设计策略包括基于分子建模的方法，以及对该系列的优化工作，以获得具有良好口服剂量暴露的泛基因型覆盖率。这项工作的关键要素之一是P2喹啉基团的螺环化，它刚性化并限制了结合构象，从而提供了一个新的核心。该小组的第二个重点还在于提高针对基因型3a和基因型1b关键突变体的活性。结构化学与分子建模的合理应用指导了结构与活性关系的设计和优化，从而鉴定出具有优良泛基因型活性和安全性的临床候选药物MK-8831。