6-溴-1,2,3,4-四氢喹啉 | 22190-35-8

• 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-溴-1,2,3,4-四氢喹啉
• 英文名称: 6-bromo-1,2,3,4-tetrahydroquinoline
• CAS: 22190-35-8
• 化学式: C₉H₁₀BrN
• mdl: MFCD04966989
• 分子量: 212.089
• InChiKey: WEHMHBSITKCQBY-UHFFFAOYSA-N

物化性质

• 沸点：
  303.1±31.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-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-Bromo-1,2,3,4-tetrahydroquinoline
CAS number: 22190-35-8

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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: C9H10BrN
Molecular weight: 212.1

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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 bromide.

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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-溴-1,2,3,4-四氢喹啉 在 copper(l) iodide 、 溴 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 5-溴-6-甲氧基喹啉
  参考文献：
  名称：

  区域选择性溴化：溴化甲氧基喹啉的合成

  摘要：

  简单的合成方法为有价值的多官能溴化methoxyquinolines合成所述10 - 13，20 - 21，和24 - 25。描述了三种区域选择性途径，以方便地在C-2，C-3和C-5位置上使用分子溴在温和的反应条件下通过连续的反应步骤制备溴化甲氧基喹啉。在溴化6-溴-8-甲氧基-1,2,3,4-四氢喹啉（8）的同时选择性地得到3,6-二溴-8-甲氧基喹啉（10）和3,5,6-三溴-8-甲氧基喹啉（8）。11），6,8-二甲氧基-1,2,3,4-四氢喹啉（9）导致形成3-bromo-6,8-dimethoxyqinoline（12）和tribromide 13。另一方面，直接溴化6-甲氧基-17和6,8-二甲氧基喹啉（19）得到5-溴衍生物20和21。然而，反应3，6-二甲氧基喹啉（8）导致二溴化形成2，5-二溴喹啉（24）。此过程选择性地导致喹啉环在C-2和C-5位置均被官能化。

  DOI：

  10.1016/j.tet.2017.07.044
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 6-溴-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  铜催化水合二羧酸二叔丁酯的氧催化氧化成偶氮二甲酸二叔丁酯及其在温和条件下对1,2,3,4-四氢喹啉的脱氢作用

  摘要：

  用均相的CuI和偶氮二甲酸二叔丁酯开发了一种新型的共催化体系，用于在温和条件下对1,2,3,4-四氢喹啉进行好氧脱氢。发达共催化体系是由二-叔丁基偶氮二羧酸酯介导的二- 1,2,3,4-四氢喹啉和好氧氧化再生的脱氢叔丁基偶氮二羧酸酯选自二叔使用分子氧作为丁基hydrazodicarboxylate终端氧化剂。发达的铜和偶氮二羧酸二叔丁酯助催化体系有效地合成了各种喹啉。

  DOI：

  10.1021/acs.orglett.6b03166

文献信息

• [EN] GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE GLYCOLATE OXYDASE POUR LE TRAITEMENT D'UNE MALADIE
  申请人：BIOMARIN PHARM INC

  公开号：WO2020257487A1

  公开（公告）日：2020-12-24

  Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.

  本文描述了化合物、制备这种化合物的方法、含有这种化合物的药物组合物和药物，以及使用这种化合物治疗或预防与甘氧酸代谢缺陷相关的疾病或紊乱的方法，例如与甘氧酸氧化酶（GO）或草酸代谢变化相关的疾病或紊乱。这些疾病或紊乱包括与产生过多草酸相关的甘氧酸代谢紊乱，例如原发性高草酸尿症。
• 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。
• Spin Delocalization, Polarization, and London Dispersion Forces Govern the Formation of Diradical Pimers
  作者：Joshua P. Peterson、Arkady Ellern、Arthur H. Winter

  DOI：10.1021/jacs.0c00190

  日期：2020.3.18

  divergent dimerization be-havior by measuring the strength of each radical association by variable-temperature EPR spectroscopy, determining the mode of dimerization (sigma or pi dimer) by UV-Vis spectroscopy and X-ray crystallography, and performing computational analysis. We evaluated three different hypotheses to explain the difference in the dimerization behavior: (1) that the dimerization behavior

  一些自由基足够稳定以被分离，但大多数要么是不稳定的瞬态物质，要么作为与二聚体形式平衡的亚稳定物质存在，通常是自旋配对 sigma 二聚体或 pi 二聚体（pimer）。为了深入了解二聚化的不同模式，我们合成并评估了一个包含 15 个芳基二氰基甲基自由基的库，以探索导致 sigma 与 pi 二聚化的结构和分子参数。我们通过变温 EPR 光谱测量每个自由基结合的强度，通过紫外-可见光谱和 X 射线晶体学确定二聚体（σ 或 pi 二聚体）的模式，并进行计算分析来评估发散二聚化行为。我们评估了三种不同的假设来解释二聚化行为的差异：(1) 二聚化行为是由自由基自旋密度决定的；(2) 它是由自由基极化率决定的；(3) 它是由二聚体的伦敦分散稳定性决定的。然而，没有单一参数模型本身是可预测的。结合计算的自旋离域度或自由基极化率以及计算的 pi 二聚体中有吸引力的伦敦色散力的估计值的双参数模型导致了对 sigma
• [EN] INTRACELLULAR RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS MODULATEURS DE RÉCEPTEURS INTRACELLULAIRES ET PROCÉDÉS DE PRODUCTION ET D'UTILISATION DE CEUX-CI
  申请人：LIGAND PHARM INC

  公开号：WO2006019716A1

  公开（公告）日：2006-02-23

  This invention relates to compounds of Formula I, II or III with the definitions of R1-R10 according to claim 1 that bind to intracellular receptors and/or modulate activity of intracellular receptors, and to methods for making and using such compounds.

  这项发明涉及具有根据权利要求1中R1-R10的定义的化合物I、II或III，这些化合物与细胞内受体结合和/或调节细胞内受体活性，并涉及制备和使用这类化合物的方法。
• Hydrogenation of Quinaldine and Benzylic Aldehydes both Separately and Combined in a Tandem Hydrogenation–Reductive Alkylation of Quinaldine by Aldehydes with Iridium Benzoquinoline Catalysts
  作者：Michael G. Manas、Jonathan Graeupner、Laura J. Allen、Graham E. Dobereiner、Kerry C. Rippy、Nilay Hazari、Robert H. Crabtree

  DOI：10.1021/om400267n

  日期：2013.8.26

  under mild conditions. Our best catalyst is active in a significantly wider range of solvents than our previous systems. In the presence of a suitable base, the Ir(III) species is also able to hydrogenate the C═O bonds of aldehydes. When quinolines and aldehydes are present together, the Ir(III) complex catalyzes a tandem reaction in which the quinoline is first hydrogenated to a tetrahydroquinoline that

  Ir（III）的一系列环金属化苯并喹啉络合物在温和条件下催化喹啉杂环的氢化。与我们以前的系统相比，我们最好的催化剂在更大范围的溶剂中具有活性。在合适的碱存在下，Ir（III）物种也能够氢化醛的C = O键。当喹啉和醛一起存在时，Ir（III）络合物催化串联反应，在该反应中，喹啉首先被氢化为四氢喹啉，随后被醛还原烷基化。还原性烷基化与醛加氢成醇竞争，因此烷基化的四氢喹啉的高收率需要存在过量的醛。