6-三氟甲基靛红 | 343-69-1

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟靛红系列
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-三氟甲基靛红
• 中文别名: 6-(三氟甲基)吲哚啉-2,3-二酮
• 英文名称: 6-(trifluoromethyl)indoline-2,3-dione
• 英文别名: 6-trifluoromethylisatin；6-(Trifluoromethyl)-1H-indol-2,3-dione；6-(trifluoromethyl)-1H-indole-2,3-dione
• CAS: 343-69-1
• 化学式: C₉H₄F₃NO₂
• 分子量: 215.131
• InChiKey: CYVMRSKFRIKMQL-UHFFFAOYSA-N

物化性质

• 密度：
  1.525±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-(Trifluoromethyl)indoline-2,3-dione
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: 6-(Trifluoromethyl)indoline-2,3-dione
CAS number: 343-69-1

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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: C9H4F3NO2
Molecular weight: 215.1

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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：

  6-三氟甲基靛红 在 potassium carbonate 、 一水合肼 作用下， 以 水 为溶剂， 反应 13.0h， 生成 (7-Trifluoromethyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)-hydrazine
  参考文献：
  名称：

  Joshi; Dandia; Baweja, Journal of the Indian Chemical Society, 1989, vol. 66, # 8-10, p. 690 - 693

  摘要：

  DOI：
• 作为产物：
  描述：

  间氨基三氟甲苯 在 盐酸 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 14.0h， 生成 6-三氟甲基靛红
  参考文献：
  名称：

  羟吲哚的催化对映选择性氟化

  摘要：

  我们开发了一种高效催化对映选择性氟化的羟吲哚衍生物。在催化量的手性 Pd 配合物 2 (2.5 mol%) 存在下，各种底物，包括芳基和烷基取代的羟吲哚，以高度对映选择性的方式（高达 96% ee）氟化。此外，当 R 是氢原子时，对映选择性氟化然后溶剂分解得到单氟化酯，ee 高达 93%。据我们所知，这是羟吲哚催化对映选择性氟化的第一个例子。

  DOI：

  10.1021/ja0513077

文献信息

• Asymmetric Intermolecular Rauhut−Currier Reaction for the Construction of 3,3-Disubstituted Oxindoles with Quaternary Stereogenic Centers
  作者：Hongyu Wang、Kaiye Wang、Yunquan Man、Xiaonan Gao、Limin Yang、Yanfei Ren、Na Li、Bo Tang、Gang Zhao

  DOI：10.1002/adsc.201700649

  日期：2017.11.23

  remote cross Rauhut−Currier reaction utilizing vinyl ketones and para‐quinone methides derived from isatins was realized, which was successfully catalyzed using bifunctional phosphines, furnishing chiral 3,3‐disubstituted oxindoles in excellent enantioselectivities and high yields. The mechanistic studies demonstrated the key role of the alkyl hydrogen of the vinyl ketones, which conceivably interacted

  实现了利用乙烯基酮和衍生自靛红的对苯二甲酰甲烷进行的远程Rauhut-Currier交叉反应，该反应已成功使用双官能膦催化，以优异的对映选择性和高收率提供了手性3,3-二取代的羟吲哚。机理研究证明了乙烯基酮的烷基氢的关键作用，可以想象它通过氢键与对苯二甲酰甲基羰基通过氢键相互作用，为新型不对称反应的设计提供了新的见识。
• Novel Synthesis of 4- or 6-Substituted Indirubin Derivatives
  作者：Aiying Zhang、Mingfeng Yu、Tian Lan、Zenglu Liu、Zhenmin Mao

  DOI：10.1080/00397910903318591

  日期：2010.9.30

  A simple and convenient route for synthesis of a series of 4- or 6-substituted indirubin derivatives by oxidation and subsequent condensation of indoxyl and isatin is described. Acidic reaction conditions are crucial to the condensation of 4-substituted derivatives, whereas for the condensation of 6-substituted derivatives, both acidic and basic conditions work well.

  描述了通过氧化和随后缩合吲哚酚和靛红来合成一系列 4-或 6-取代的靛玉红衍生物的简单方便的途径。酸性反应条件对 4-取代衍生物的缩合至关重要，而对于 6-取代衍生物的缩合，酸性和碱性条件都适用。
• Pyridazinedione compounds useful in treating neurological disorders
  申请人：Imperial Chemical Industries, PLC

  公开号：US05599814A1

  公开（公告）日：1997-02-04

  The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.

  本发明涉及吡啶并[4,5-b]喹啉及其药用盐，它们是兴奋性氨基酸拮抗剂，在需要此类拮抗作用时非常有用，例如在治疗神经系统疾病时。该发明还提供含有吡啶并[4,5-b]喹啉作为活性成分的药物组合物，以及治疗神经系统疾病的方法。
• Iron-catalyzed C(sp³)–H functionalization of methyl azaarenes: a green approach to azaarene-substituted α- or β-hydroxy carboxylic derivatives and 2-alkenylazaarenes
  作者：Danwei Pi、Kun Jiang、Haifeng Zhou、Yuebo Sui、Yasuhiro Uozumi、Kun Zou

  DOI：10.1039/c4ra10939b

  日期：——

  An iron-catalyzed C(sp³)–H functionalization of methyl azaarenes with carbonyls to access the title compounds have been described.

  使用铁催化的C(sp³)-H官能团化方法，将甲基氮杂芳烃与羰基化合物反应，合成了目标化合物。

• Discovery of an eIF4A Inhibitor with a Novel Mechanism of Action
  作者：Christopher J. Zerio、Tyler A. Cunningham、Allison S. Tulino、Erin A. Alimusa、Thomas M. Buckley、Kohlson T. Moore、Matthew Dodson、Nathan C. Wilson、Andrew J. Ambrose、Taoda Shi、Jared Sivinski、Derek J. Essegian、Donna D. Zhang、Stephan C. Schürer、Jonathan H. Schatz、Eli Chapman

  DOI：10.1021/acs.jmedchem.1c01014

  日期：2021.11.11

  Increased protein synthesis is a requirement for malignant growth, and as a result, translation has become a pharmaceutical target for cancer. The initiation of cap-dependent translation is enzymatically driven by the eukaryotic initiation factor (eIF)4A, an ATP-powered DEAD-box RNA-helicase that unwinds the messenger RNA secondary structure upstream of the start codon, enabling translation of downstream

  增加蛋白质合成是恶性生长的必要条件，因此，翻译已成为癌症的药物靶标。帽依赖性翻译的起始由真核起始因子 （eIF）4A 酶促驱动，这是一种 ATP 驱动的死盒 RNA 解旋酶，可解开起始密码子上游的信使 RNA 二级结构，从而能够翻译下游基因。筛选 eIF4A ATP 酶活性抑制剂产生了一个有趣的结果，令人惊讶的是，它不是 ATP 竞争性的。药物化学活动产生了新型 eIF4A 抑制剂 28，它降低了 BJAB Burkitt 淋巴瘤细胞活力。生化和细胞研究、分子对接和功能测定发现，28 是一种 RNA 竞争性、ATP 非竞争性抑制剂，它参与 eIF4A RNA 凹槽中的一个新口袋，并通过干扰适当的 RNA 结合和抑制 ATP 水解来抑制解旋活性。通过这种独特的机制抑制 eIF4A 可能为靶向许多致癌途径的这个有希望的交点提供新的策略。