7-(三氟甲基)喹唑啉-4(3H)-酮 | 16499-58-4

• 物质功能分类: 有机原料 - 有机氟化合物
• 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: 7-(三氟甲基)喹唑啉-4(3H)-酮
• 英文名称: 7-(trifluoromethyl)quinazolin-4(3H)-one
• 英文别名: 7-(Trifluoromethyl)quinazolin-4(3H)-one；7-(trifluoromethyl)-3H-quinazolin-4-one
• CAS: 16499-58-4
• 化学式: C₉H₅F₃N₂O
• 分子量: 214.147
• InChiKey: PPQZFZZPLINSJL-UHFFFAOYSA-N

物化性质

• 熔点：
  225-227 °C(Solv: ethanol (64-17-5))
• 沸点：
  290.0±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 7-(Trifluoromethyl)quinazolin-4-ol
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: 7-(Trifluoromethyl)quinazolin-4-ol
CAS number: 16499-58-4

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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: C9H5F3N2O
Molecular weight: 214.1

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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：

  7-(三氟甲基)喹唑啉-4(3H)-酮 在 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 1-phenyl-3-[5-(2-{[7-(trifluoromethyl)quinazolin-4-yl]amino}ethyl)-1,3-thiazol-2-yl]urea
  参考文献：
  名称：

  药物性质优化：口服生物利用喹唑啉基多靶点激酶抑制剂的发现。

  摘要：

  为了开发新的癌症疗法，我们已经在MOLM-13和MV4-11白血病模型以及大肠和胰腺动物模型中报告了临床候选药物BPR1K871（1）作为有效的抗癌化合物。由于BPR1K871缺乏口服生物利用度，我们继续通过药物样性质优化来寻找口服生物利用度类似物。我们优化了1的理化特性（PCP）以及体外大鼠肝脏微粒体的稳定性，同时监测了HCT-116细胞系中的极光激酶抑制和细胞抗增殖活性。喹唑啉核心1的6位和7位的结构修饰导致34被鉴定为口服生物利用型（F％= 54）多激酶抑制剂，对多种癌细胞系表现出有效的抗增殖活性。

  DOI：

  10.1016/j.bioorg.2020.103689
• 作为产物：
  描述：

  2-氨基-4-三氟甲基苯甲酸 在 potassium phosphate 、 copper(l) iodide 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 35.0h， 生成 7-(三氟甲基)喹唑啉-4(3H)-酮
  参考文献：
  名称：

  以 BrCF2COOEt 作为 C1 源的铜催化碳环化一般合成含氮杂环化合物

  摘要：

  已经开发出一种实用且高效的铜催化 2-官能化苯胺与溴二氟乙酸乙酯的碳环化反应。在此转化中，溴二氟乙酸乙酯通过四次裂解用作 C1 源。该反应可以得到多种含氮杂环化合物，且产率令人满意，官能团相容性优异。

  DOI：

  10.1021/acs.joc.3c02827

文献信息

• Potential Antimalarials. IX. Di-mannich Bases of 4-(7′-trifluoro-methylquinazolin-4′-ylamino)phenol and 4-(7′-Trifluoromethylquinolin-4′-ylamino)phenol
  作者：GB Barlin、C Jiravinyu

  DOI：10.1071/ch9900311

  日期：——

  Syntheses are reported for a series of di-Mannich bases of 4-(7′-trifluoromethylquinazolin-4′-ylamino)phenol derived from 4-chloro-7-trifluoromethylquinazoline with the di-Mannich bases of 4-aminophenol. Some analogous quinolines were prepared similarly. When tested for antimalarial activity against Plasmodium falciparum in vitro, the quinazolines were rather less active than the corresponding quinolines.

  报告了一系列 4-(7′-三氟甲基喹唑啉-4′-基氨基)苯酚二曼尼希碱的合成，这些苯酚二曼尼希碱来自 4-氯-7-三氟甲基喹唑啉和 4-氨基苯酚的二曼尼希碱。一些类似的喹啉类化合物也是用类似方法制备的。在对恶性疟原虫进行体外抗疟活性测试时，这些喹唑啉类化合物的活性比相应的喹啉类化合物低。
• Photoinduced homolytic decarboxylative acylation/cyclization of unactivated alkenes with α-keto acid under external oxidant and photocatalyst free conditions: access to quinazolinone derivatives
  作者：Bin Sun、Rongcheng Shi、Kesheng Zhang、Xiaoli Tang、Xiayue Shi、Jiayun Xu、Jin Yang、Can Jin

  DOI：10.1039/d1cc02415a

  日期：——

  A novel and green strategy for the synthesis of acylated quinazolinone derivatives via photo-induced decarboxylative cascade radical acylation/cyclization of quinazolinone bearing unactivated alkenes has been developed. The protocol provides a novel route to access acyl radicals from α-keto acids through a self-catalyzed energy transfer process. Most importantly, the reaction proceeded smoothly without

  已经开发了通过光诱导的带有未活化烯烃的喹唑啉酮的脱羧级联自由基酰化/环化反应来合成酰化喹唑啉酮衍生物的新颖和绿色策略。该协议提供了一种通过自催化能量转移过程从α-酮酸中获取酰基的新颖途径。最重要的是，该反应在没有任何外部光催化剂，添加剂或氧化剂的情况下可顺利进行，并且在阳光照射下，在流动条件下很容易按比例放大。
• N-coating heterocyclic compounds
  申请人：——

  公开号：US20030176454A1

  公开（公告）日：2003-09-18

  A compound of the formula (I): wherein A is a hydrogen atom, an optionally substituted, unsaturated, N-containing heterocyclic group or a group of the formula (a): wherein R is an optionally substituted aryl group or an optionally substituted heterocyclic group; M is —(CH 2 )n-, —(CH 2 )n-O—(CH 2 )m-or —(CH 2 )n-NH—(CH 2 )m-, wherein n and m are independently 0, 1 or 2; Q is an optionally substituted cycloalkylene group, an optionally substituted arylene group or an optionally substituted divalent heterocyclic group; and the moiety of the formula (b): is an optionally substituted, unsaturated, mono-, di-, tri- or tetra-cyclic, N-containing heterocyclic group which may contain additional hetero atom(s) selected from the group consisting of nitrogen, oxygen and sulfur atoms as the ring member(s), its prodrug or a pharmaceutically acceptable salt thereof.

  公式(I)的化合物：其中A是氢原子，一个可选地取代的、不饱和的、含氮的杂环基团，或者公式(a)的基团：其中R是一个可选地取代的芳香族基团或者一个可选地取代的杂环基团；M是—(CH2)n-, —(CH2)n-O—(CH2)m-或—(CH2)n-NH—(CH2)m-，其中n和m各自为0、1或2；Q是一个可选地取代的环烷基烯基团、一个可选地取代的芳香族基团或者一个可选地取代的二价杂环基团；以及公式(b)的部分：是一个可选地取代的、不饱和的、单环、双环、三环或四环的、含氮的杂环基团，它可以包含作为环成员的额外杂原子，选自由氮、氧和硫原子组成的组，其前药或药用盐。
• Rhodium-Catalyzed Asymmetric N−H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (−)-Chaetominine
  作者：Yirong Zhou、Bernhard Breit

  DOI：10.1002/chem.201705059

  日期：2017.12.22

  An unprecedented asymmetric N−H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo‐, regio‐, and enantioselectivities with broad functional

  通过手性双齿二膦配体的铑催化成功地实现了喹唑啉酮与丙二烯和烯丙基碳酸酯的前所未有的不对称NH键化。该方法的高效率和实用性通过1 mol％的低催化剂负载量以及出色的化学，区域和对映选择性以及广泛的官能团相容性得到证明。此外，这种新开发的策略被用作（-）-chaetominine的第一个对映选择性正式全合成中的关键步骤。
• 複素環化合物を用いる有害節足動物防除方法
  申请人：住友化学株式会社

  公开号：JP2020189891A

  公开（公告）日：2020-11-26

  【課題】有害節足動物の防除方法を提供すること。【解決手段】式（Ｉ）〔式中、Ｑは、式Ｑ１で示される基等を表し、Ｚは酸素原子等を表し、Ａ1はＣＲ4a等を表し、Ａ2は窒素原子等を表し、Ｂ1は窒素原子又はＣＲ6a等を表し、Ｂ2はＣＲ1等を表し、Ｂ3は窒素原子又はＣＲ6c等を表し、Ｂ4は窒素原子又はＣＲ6d等を表し、Ｒ1はＣ１−Ｃ６鎖式炭化水素基等を表し、Ｒ2はＣ１−Ｃ６アルキル基等を表し、Ｒ3a、Ｒ3b及びＲ3dは、同一又は相異なり、Ｃ１−Ｃ６鎖式炭化水素基等を表し、Ｒ4a、Ｒ6a、Ｒ6c及びＲ6dは、同一又は相異なり、Ｃ１−Ｃ６鎖式炭化水素基等を表し、ｎは０、１又は２を表す。〕で示される化合物又はそのＮオキシドは、有害節足動物を防除することができる。【選択図】なし

  提供有害节肢动物防除方法的解决方案是通过式（Ｉ）中所示的化合物或其N氧化物来实现的，其中Q代表表示基等的Q1式，Z代表氧原子等，A1代表CR4a等，A2代表氮原子等，B1代表氮原子或CR6a等，B2代表CR1等，B3代表氮原子或CR6c等，B4代表氮原子或CR6d等，R1代表C1-C6链式烃基等，R2代表C1-C6烷基等，R3a、R3b和R3d代表相同或不同的C1-C6链式烃基等，R4a、R6a、R6c和R6d代表相同或不同的C1-C6链式烃基等，n代表0、1或2。这些化合物或其N氧化物可以用于防除有害节肢动物。【选择图】无