3-I碘-8-硝基喹啉 | 497084-46-5

• 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: 3-I碘-8-硝基喹啉
• 中文别名: 3-碘-8-硝基喹啉
• 英文名称: 3-iodo-8-nitroquinoline
• CAS: 497084-46-5
• 化学式: C₉H₅IN₂O₂
• mdl: MFCD09261162
• 分子量: 300.055
• InChiKey: JTOBADNVHAZTAP-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 沸点：
  401.2±30.0 °C(Predicted)
• 密度：
  1.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 储存条件：
  存放条件：室温、密封且干燥环境下保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Iodo-8-nitroquinoline
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: 3-Iodo-8-nitroquinoline
CAS number: 497084-46-5

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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: C9H5IN2O2
Molecular weight: 300.1

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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 Iodide.

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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：

  3-I碘-8-硝基喹啉 在 铁粉 作用下， 以 甲醇 为溶剂， 生成 3-碘喹啉-8-胺
  参考文献：
  名称：

  Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms

  摘要：

  A series of 3-subsituted quinolinehydroxamic acids has been synthesised and evaluated for their effect on human lung cancer cell line (A549), human colorectal cancer cell line (HCT116) and HDAC isoforms 1, 2, 6, and 8. The results indicated that substitution at C3 of quinoline is favoured for HDAC6 selectivity. Two compounds (25 and 26) were also found to be potent anti-proliferative compounds with IC50 values ranging from 1.29 to 2.13 mu M against A549 and HCT116 cells. These compounds displayed remarkable selectivity for HDAC6 over other HDAC isoforms with nanomolar IC50 values. Western blot analysis revealed that compounds of this series activate apoptotic caspase pathway as indicated by cleavage of caspase 3, 8, and 9 and also increase phosphorylated H2AX thus inducing DNA double strand fragmentation in a concentration dependent manner. Flow cytometric analysis also displayed a dose dependent increase of cell population in sub G1 phase.

  DOI：

  10.1080/14756366.2020.1839446
• 作为产物：
  描述：

  2-硝基苯胺 在 叔丁基过氧化氢 、 碘 、 sodium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 26.25h， 生成 3-I碘-8-硝基喹啉
  参考文献：
  名称：

  Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

  摘要：

  An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ^•CBr₃ radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

  DOI：

  10.1021/acs.joc.9b00942

文献信息

• Halogen Bond-Assisted Electron-Catalyzed Atom Economic Iodination of Heteroarenes at Room Temperature
  作者：Imran Kazi、Somraj Guha、Govindasamy Sekar

  DOI：10.1021/acs.joc.9b00174

  日期：2019.6.7

  halogen bond-assisted electron-catalyzed iodination of heteroarenes has been developed for the first time under atom economic condition at room temperature. The iodination is successful with just 0.55 equiv of iodine and 0.50 equiv of peroxide. The kinetic study indicates that the reaction is elusive in the absence of a halogen bond between the substrate and iodine. The formation of a halogen bond, its

  在室温下原子经济条件下，首次开发了卤素键辅助的电子催化的杂芳烃碘化反应。仅用0.55当量的碘和0.50当量的过氧化物就能成功进行碘化。动力学研究表明，在底物和碘之间不存在卤素键的情况下，该反应难以捉摸。卤素键的形成，其在降低该反应的活化势垒中的重要性，反应混合物中自由基中间体的存在以及反应的区域选择性已通过数个对照实验，光谱分析和量子化学计算得到了证明。
• The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil
  作者：Uttam Dutta、Arghya Deb、David W. Lupton、Debabrata Maiti

  DOI：10.1039/c5cc07799k

  日期：——

  A radical based direct C-H iodination protocol for quinolines, quinolones, pyridones, pyridines, and uracil has been developed. The iodination occurs in a C3 selective manner for quinolines and quinolones. Pyridones...

  已经开发出基于自由基的直接CH碘化方案，用于喹啉，喹诺酮，吡啶酮，吡啶和尿嘧啶。碘化以喹啉和喹诺酮类化合物的C3选择性方式发生。吡啶酮...
• Metal-free synthesis of N-fused heterocyclic iodides via C–H functionalization mediated by tert-butylhydroperoxide
  作者：Krishna K. Sharma、Dhananjay I. Patel、Rahul Jain

  DOI：10.1039/c5cc04013b

  日期：——

  Direct, regioselective and metal-free synthesis of fused N-heterocyclic iodides is reported.

  直接、区域选择性和无金属合成杂环碘化物的报道。
• Design, Synthesis, and Evaluation in Vitro of Quinoline-8-carboxamides, a New Class of Poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) Inhibitor
  作者：Anna-Marie Lord、Mary F. Mahon、Matthew D. Lloyd、Michael D. Threadgill

  DOI：10.1021/jm8013629

  日期：2009.2.12

  prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium−bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement

  聚（ADP-核糖）聚合酶-1是药物设计中的重要目标酶。抑制剂具有多种治疗活性。设计了一系列喹啉-8-羧酰胺以通过分子内氢键维持所需的药效团构象。通过Pd催化的偶联（Suzuki，Sonogashira，Stille）与3-碘喹啉-8-羧酰胺合成3-取代的喹啉-8-羧酰胺，这是在最后一步引入多样性的有效方法。通过在2,8-二溴喹啉的2-位进行选择性Pd催化偶联反应，然后通过中间体2-（烷基/芳基）-8-溴喹啉的锂溴交换和反应制备2-取代的喹啉-8-甲酰胺。与异氰酸三甲基甲硅烷基酯。分子内氢键通过X射线和NMR确认。用于抑制人重组PARP-1活性的3-取代化合物的SAR显示需要一个小的狭窄基团。2位取代基增加了效能，最活跃的2-甲基喹啉-8-羧酰胺具有IC50 = 500 nM（5-氨基异喹啉-1-酮（5-AIQ，标准水溶性抑制剂）的IC 50 = 1.8μM）。
• Iterative Arylation of Amino Acids and Aliphatic Amines via δ‐C(sp ³ )−H Activation: Experimental and Computational Exploration
  作者：Srimanta Guin、Pravas Dolui、Xinglong Zhang、Satyadip Paul、Vikas Kumar Singh、Sukumar Pradhan、Hediyala B. Chandrashekar、S. S. Anjana、Robert S. Paton、Debabrata Maiti

  DOI：10.1002/anie.201900479

  日期：2019.4.16

  mostly up to the γ‐position. In the present work, we demonstrate the diverse (hetero)arylation of amino acids and analogous aliphatic amines selectively at the remote δ‐position by tuning the reactivity controlled by ligands. An organopalladium δ‐C(sp3)−H activated intermediate has been isolated and crystallographically characterized. Mechanistic investigations carried out experimentally in conjunction

  定向C H功能化已实现为传统方法的补充工具，可直接访问非蛋白原性氨基酸。尽管这样的过程主要限于γ位置。在当前的工作中，我们通过调节配体控制的反应性，证明了在远端δ位选择性地使氨基酸和类似的脂肪族胺具有多种（杂）芳基化作用。已分离出有机钯δ-C（sp 3）-H活化中间体，并进行了晶体学表征。实验研究与计算研究相结合进行的机理研究揭示了取决于基材结构的机理图上的差异。