6-硝基-1,2,3,4-四氢喹啉 | 14026-45-0

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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: 6-硝基-1,2,3,4-四氢喹啉
• 中文别名: 6-硝基四氢喹啉
• 英文名称: 6-nitro-1,2,3,4-tetrahydroquinoline
• 英文别名: 6-Nitro-tetrahydrochinolin；6-Nitro-1,2,3,4-tetrahydro-chinolin
• CAS: 14026-45-0
• 化学式: C₉H₁₀N₂O₂
• mdl: MFCD00541472
• 分子量: 178.191
• InChiKey: ASVYHMUYLBMSKW-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C(Solv: acetic acid, 50% (64-19-7))
• 沸点：
  341.4±31.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Nitro-1,2,3,4-tetrahydroquinoline
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-Nitro-1,2,3,4-tetrahydroquinoline
CAS number: 14026-45-0

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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: C9H10N2O2
Molecular weight: 178.2

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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.

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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

制备方法与用途

6-硝基四氢喹啉可以作为有机合成中间体和医药中间体，主要应用于实验室研发和化工生产的相关过程。

反应信息

• 作为反应物：
  描述：

  6-硝基-1,2,3,4-四氢喹啉 在 perylene diimide covalent immobilized to SiO₂ nanospheres 、 air 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以91%的产率得到6-硝基喹啉
  参考文献：
  名称：

  在环境条件下，微小有机半导体在可见光促进下对 N-杂环进行高效有氧脱氢

  摘要：

  基于苝二酰亚胺 (PDI) 有机半导体开发了一种高效的可重复使用的催化系统，用于在可见光下对 N-杂环进行有氧脱氢。这种没有任何添加剂的实用催化体系在环境条件下进行。N-杂芳烃的微小聚集体被认为是天然产物、药物化学和材料科学中的特权结构。 [1] 因此，合成芳烃的温和方法的发展引起了有机合成化学家的兴趣[2]。将取代基选择性地引入 N-杂芳烃是一项艰巨的挑战，而对于相应的 N-杂环来说，这相对容易实现。例如，四氢喹啉可以很容易地进行 6 位亲电取代功能化，脱氢可得到相应的取代喹啉[3]。因此，N-杂环脱氢为N-杂芳烃被认为是一种可行的方法。与热促进的有机反应相比，利用可见光能作为有机转化的驱动力具有吸引力，因为它是一种温和、安全且易于处理的能源。 [4] 一般来说，N-杂环的可见光促进脱氢有两个亚类：无受体[2e,5]和受体辅助[3,6]，这取决于是否涉及氢受体。受体辅助脱氢，尤其是使用氧

  DOI：

  10.1002/ejoc.202000170
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 在 四氢吡咯 、 硫酸 、 potassium nitrate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.08h， 生成 6-硝基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  6-Nitro-1,2,3,4-四氢喹啉的合成：区域选择性硝化的实验和理论研究

  摘要：

  关于四氢喹啉硝化的文献的修订产生了许多不一致之处。因此，我们在实验和理论水平上对四氢喹啉及其几种 N 保护衍生物的硝化进行了深入研究。通常，硝化是在酸性条件下进行的，因此四氢喹啉会被 N-质子化；然而，如果氨基被保护，中性系统将是进行硝化的系统。已经探索了不同的保护基团，不仅有电子和空间效应，而且还有脱保护条件。此外，还研究了不同的试剂和反应条件。从这项研究中，我们已经能够在 6 位实现硝化的总区域选择性。已经进行了非常详细的 NMR 研究以明确表征四种硝基异构体。同时，进行了与实验结果一致的计算研究。为此，通过使用 B3LYP/6-31++G ** 级别的计算，所有四种硝基异构体的中性和 N 质子化的 σ​​ 配合物都在气相和水凝聚相中进行了优化。

  DOI：

  10.1002/ejoc.201001459

文献信息

• Ruthenium(II)-Catalyzed Regioselective C-8 Hydroxylation of 1,2,3,4-Tetrahydroquinolines
  作者：Changjun Chen、Yixiao Pan、Haoqiang Zhao、Xin Xu、Zhenli Luo、Lei Cao、Siqi Xi、Huanrong Li、Lijin Xu

  DOI：10.1021/acs.orglett.8b02926

  日期：2018.11.2

  Ru(II)-catalyzed chelation-assisted highly regioselective C8-hydroxylation of 1,2,3,4-tretrahydroquinolines has been developed. Various 1,2,3,4-tetrahydroquinolines underwent smooth C8–H hydroxylation with cheap and safe K2S2O8 as the oxidant and oxygen source to furnish the corresponding products in good to excellent yields with high tolerance of the functional groups. The choice of a readily installable

  已经开发了Ru（II）催化的1,2,3,4-四氢喹啉的螯合辅助的高区域选择性C8-羟基化反应。各种1,2,3,4-四氢喹啉经过顺畅的C8–H羟基化反应，并以廉价且安全的K 2 S 2 O 8作为氧化剂和氧源，以高收率和高官能度耐受性提供了相应的产品。选择易于安装和拆卸的N-嘧啶导向基团是催化的关键。机理研究表明六元钌循环中间体参与了催化循环。该方法还可以扩展到其他（杂）芳烃CH键的直接羟基化反应。
• Synthesis and Characterization of Iron–Nitrogen-Doped Graphene/Core–Shell Catalysts: Efficient Oxidative Dehydrogenation of <i>N</i>-Heterocycles
  作者：Xinjiang Cui、Yuehui Li、Stephan Bachmann、Michelangelo Scalone、Annette-Enrica Surkus、Kathrin Junge、Christoph Topf、Matthias Beller

  DOI：10.1021/jacs.5b05674

  日期：2015.8.26

  and stable core-shell catalysts. In this respect, we present the synthesis and characterization of iron oxides surrounded by nitrogen-doped-graphene shells immobilized on carbon support (labeled FeOx@NGr-C). Active catalytic materials are obtained in a simple, scalable and two-step method via pyrolysis of iron acetate and phenanthroline and subsequent selective leaching. The optimized FeOx@NGr-C catalyst

  纳米催化的一个重要目标是开发灵活有效的方法来制备活性稳定的核壳催化剂。在这方面，我们介绍了由固定在碳载体上的氮掺杂石墨烯壳包围的氧化铁的合成和表征（标记为 FeOx@NGr-C）。通过醋酸铁和菲咯啉的热解和随后的选择性浸出，以简单、可扩展的两步法获得活性催化材料。优化的 FeOx@NGr-C 催化剂在几种 N-杂环的氧化脱氢中表现出高活性。药学相关喹啉的合成证明了这种良性方法的效用。此外，机理研究证明反应通过超氧自由基阴离子（·O2(-)）进行。
• Nitrogen-coordinated cobalt nanocrystals for oxidative dehydrogenation and hydrogenation of N-heterocycles
  作者：Yue Wu、Zheng Chen、Weng-Chon Cheong、Chao Zhang、Lirong Zheng、Wensheng Yan、Rong Yu、Chen Chen、Yadong Li

  DOI：10.1039/c9sc00475k

  日期：——

  positive charge on the Co surface, thereby promoting the reaction. In contrast, cobalt nanocrystals supported by pristine carbon (Co NCs/C) proved to be inactive for oxidative dehydrogenation, owing to the lack of nitrogen. Moreover, in Co NCs/N-C, the N-doped graphitized carbon formed a protective layer for Co NCs, which preserved the active valence of Co species and prevented the catalyst from leaching.

  赋予非贵金属通常具有贵金属的高催化活性是替代贵金属的核心但具有挑战性的目标。为此，我们利用氮的配位效应，制备了氮掺杂石墨化碳稳定的钴纳米晶（Co NCs/NC）。所获得的Co NC/NC催化剂在极其温和的条件下对N-杂环的氧化脱氢及其逆加氢过程表现出非凡的性能。即使在室温（25℃）下，氧化脱氢也能实现近乎定量的转化，这归因于氮的配位效应：Co-N的相互作用在Co表面诱导部分正电荷，从而促进反应。相比之下，由于缺乏氮，由原始碳支撑的钴纳米晶体（Co NCs/C）被证明对于氧化脱氢没有活性。此外，在Co NCs/NC中，N掺杂的石墨化碳形成了Co NCs的保护层，保留了Co物种的活性价态并防止催化剂浸出。结果发现，催化剂经过5次再生循环后仍保持优异的催化活性；相比之下，其对应的氧化钴 (CoO x /NC) 几乎没有活性。至于其机制，电子顺磁共振（EPR）分析揭示了脱氢过程中超氧阴离子自由基的
• Iodine catalyzed reduction of quinolines under mild reaction conditions
  作者：Chun-Hua Yang、Xixi Chen、Huimin Li、Wenbo Wei、Zhantao Yang、Junbiao Chang

  DOI：10.1039/c8cc04262d

  日期：——

  synthetically versatile tetrahydroquinoline molecules with I2 and HBpin is described. In the presence of iodine (20 mol%) as a catalyst, reduction of quinolines and other N-heteroarenes proceeded readily with hydroboranes as the reducing reagents. The broad functional-group tolerance, good yields and mild reaction conditions imply high practical utility.

  描述了用I 2和HBpin将喹啉还原为合成通用的四氢喹啉分子。在碘（20mol％）作为催化剂的存在下，以氢硼烷作为还原剂容易地进行喹啉和其他N-杂芳烃的还原。宽泛的官能团耐受性，良好的收率和温和的反应条件意味着较高的实用性。
• Activation of Quinolines by Cationic Chalcogen Bond Donors
  作者：P. Wonner、T. Steinke、S. M. Huber

  DOI：10.1055/s-0039-1690110

  日期：2019.9

  chalcogen bond donors in the catalytic activation of quinoline derivatives is presented. In the presence of selected catalysts, rate accelerations of up to 2300 compared to virtually inactive reference compounds are observed. The catalyst loading can be reduced to 1 mol% while still achieving nearly full conversion for electron-poor and electron-rich quinolines. Contrary to expectations, preorganized catalysts

  介绍了已经建立的以及新型的基于硒和硫的阳离子硫属元素键供体在喹啉衍生物的催化活化中的应用。在所选催化剂的存在下，与几乎无活性的参考化合物相比，观察到高达 2300 的速率加速。对于缺电子和富电子喹啉，催化剂负载量可以降低到 1 mol%，同时仍能实现几乎完全转化。与预期相反，预先组织的催化剂比更灵活的变体活性更低。