8-羟基-1,2,3,4-四氢喹啉 | 6640-50-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 8-羟基-1,2,3,4-四氢喹啉
• 中文别名: 1,2,3,4-四氢-8-羟基喹啉
• 英文名称: 1,2,3,4-tetrahydroquinolin-8-ol
• 英文别名: 8-hydroxy-1,2,3,4-tetrahydroquinoline；1.2.3.4-tetrahydro-8-hydroxy-quinoline；1,2,3,4-tetrahydro-8-quinolinol
• CAS: 6640-50-2
• 化学式: C₉H₁₁NO
• mdl: MFCD02656029
• 分子量: 149.192
• InChiKey: WYKWUPMZBGOFOV-UHFFFAOYSA-N

物化性质

• 熔点：
  121-121.5 °C
• 沸点：
  300.9±31.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R22,R52
• 海关编码：
  2933499090
• WGK Germany：
  3
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,2,3,4-Tetrahydroquinolin-8-ol
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H412: Harmful to aquatic life with long lasting effects
P273: Avoid release to the environment

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Section 3. Composition/information on ingredients.
Ingredient name: 1,2,3,4-Tetrahydroquinolin-8-ol
CAS number: 6640-50-2

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H11NO
Molecular weight: 149.2

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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

反应信息

• 作为反应物：
  描述：

  8-羟基-1,2,3,4-四氢喹啉 在 iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support 作用下， 以 乙腈 为溶剂， 100.0 ℃ 、1.5 MPa 条件下， 反应 24.0h， 以93%的产率得到8-羟基喹啉
  参考文献：
  名称：

  铁氮掺杂石墨烯/核壳催化剂的合成和表征：N-杂环的高效氧化脱氢

  摘要：

  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。

  DOI：

  10.1021/jacs.5b05674
• 作为产物：
  描述：

  5-氯-8-羟基喹啉 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 以72%的产率得到8-羟基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  DDI-6 的鉴定和合成，一种能够激活秀丽隐杆线虫和小鼠精子的喹啉类似物

  摘要：

  精子激活是雄配子能够受精的重要过程。由于秀丽隐杆线虫的过程在体外很容易重现，因此该生物体可作为研究它的极好模型。C. 线虫体内精子激活发生在精子发生过程中。包含在精子细胞内的膜细胞器 (MO) 与质膜融合，导致其内容物的细胞外释放和一些对受精必不可少的蛋白质从 MO 膜重新定位到精子表面。有趣的是，这些细胞学变化在顶体反应期间在小鼠精子中表现出类似的表现，这也代表了精子激活的一种形式，促使我们假设秀丽隐杆线虫和小鼠共享一个共同的精子激活机制。为了探索这一点，我们首先筛选了一个化学库来识别激活秀丽隐杆线虫的化合物精子。因为一种名为 DDI-6 的喹啉类似物似乎是一种候选精子激活剂，我们合成了它以用于进一步分析。这涉及市售的 5-氯-8-羟基喹啉的直接脱氯和氢解，这两个步骤都是产生 1,2,3,4-四氢-8-羟基喹啉的关键步骤，我们随后将磺酰胺基团引入到该化合物中。当线虫精子细胞单独用溶剂或新合成的

  DOI：

  10.1248/cpb.c21-00127
• 作为试剂：
  描述：

  N-Boc-4-哌啶甲酸乙酯 在 8-羟基-1,2,3,4-四氢喹啉 、 caesium carbonate 、 copper(I) bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 45.67h， 生成 tert-butyl 6-(1H-imidazol-1-yl)-1-oxo-1,3-dihydrospiro[indene-2 ,4’-piperidine]-1‘-carboxylate
  参考文献：
  名称：

  [EN] NOVEL HETEROCYCLIC DERIVATIVES USEFUL AS SHP2 INHIBITORS
  [FR] NOUVEAUX DÉRIVÉS HÉTÉROCYCLIQUES UTILES EN TANT QU'INHIBITEURS DE SHP2

  摘要：

  这项发明涉及某些新颖的吡嗪衍生物（化学式I）作为SHP2抑制剂，其化学式如下，以及它们的合成以及用于治疗SHP2介导的疾病的用途。更具体地，这项发明涉及融合杂环基衍生物，可用作SHP2的抑制剂，生产这类化合物的方法以及治疗SHP2介导的疾病的方法。

  公开号：

  WO2018172984A1

文献信息

• Structures of Addition Products of Acetylenedicarboxylic Acid Esters with Various Dinucleophiles. An application of C, H-spin-coupling constants
  作者：Ulrich Vögeli、Wolfgang von Philipsborn、Kuppuswamy Nagarajan、Mohan D. Nair

  DOI：10.1002/hlca.19780610207

  日期：1978.3.8

  Heterocyclic compounds obtained by addition of acetylenedicarboxylic acid esters to thioureas, cyclic amidines and o-difunctionalized aromatic systems have been studied by 13C-NMR. In particular, C, H-spin-coupling constants over two and three bonds were used to differentiate between the various constitutional isomers and to establish the configuration of trisubstituted exocyclic C, C-double bonds

  通过13 C-NMR研究了通过将乙炔二羧酸酯加到硫脲，环am和邻双官能化的芳族体系中得到的杂环化合物。特别地，在两个和三个键上的C，H-自旋偶联常数用于区分各种结构异构体并建立三取代的外环C，C-双键的构型。邻位顺式和反式C，H-spin偶联的构型意义和诊断价值在本系列中再次得到证明。
• Sulfonamide peri-substituted bicyclics for occlusive artery disease
  申请人：Singh Jasbir

  公开号：US20060079520A1

  公开（公告）日：2006-04-13

  Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:

  酰基磺酰胺，带有周取代的融合双环环化合物，用于治疗或预防前列腺素介导的疾病或症状。这些化合物的一般公式为 代表性示例是：
• 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。
• Selective N-cycle hydrogenation of quinolines with sodium borohydride in aqueous media catalyzed by hectorite-supported ruthenium nanoparticles
  作者：Bing Sun、Diego Carnevale、Georg Süss-Fink

  DOI：10.1016/j.jorganchem.2016.07.010

  日期：2016.10

  new catalyst containing metallic ruthenium nanoparticles intercalated in hectorite (nanoRu′@hectorite) was found to catalyze the reduction of quinoline and quinoline derivatives by NaBH4 in aqueous solution to give selectively the corresponding 1,2,3,4-tetrahydroquinolines (N-cycle hydrogenation). In most cases the reaction can be done under mild conditions (25–60 °C) without pressure equipment, conversion

  发现一种新的包含嵌入锂蒙脱石中的金属钌纳米颗粒的催化剂（nano Ru'@锂蒙脱石）可以催化NaBH 4在水溶液中还原喹啉和喹啉衍生物，从而选择性地得到相应的1,2,3,4-四氢喹啉（N -循环氢化）。在大多数情况下，该反应可以在温和的条件下（25-60°C）进行，而无需加压设备，转化率和选择性均优于99％。对于位阻衍生物，该反应可以在压力容器中在自生压力（最高9 bar）下进行。异喹啉和喹喔啉也经历选择性氮-环加氢，但是将2-苯基-喹啉加氢得到2-苯基-5,6,7,8-四氢喹啉（C-环加氢）。同位素标记实验与静电势的半经验计算相结合，支持了一种杂化氢化机理，其中涉及NaBH 4的氢化物和H 2 O的质子。催化剂纳米Ru'@锂蒙脱石可以循环再利用。
• Cobalt Encapsulated in N-Doped Graphene Layers: An Efficient and Stable Catalyst for Hydrogenation of Quinoline Compounds
  作者：Zhongzhe Wei、Yiqing Chen、Jing Wang、Diefeng Su、Minghui Tang、Shanjun Mao、Yong Wang

  DOI：10.1021/acscatal.6b01240

  日期：2016.9.2

  Porous nitrogen-doped graphene layers encapsulating cobalt nanoparticles (NPs) were prepared by the direct pyrolysis process. The resulting hybrids catalyze the hydrogenation of diverse quinoline compounds to access the corresponding tetrahydro derivatives (THQs), important molecules present in fine and bulk chemicals. Near-quantitative yields of the corresponding THQs were obtained under optimized

  通过直接热解工艺制备了包裹钴纳米颗粒（NPs）的多孔氮掺杂石墨烯层。所得的杂化物催化各种喹啉化合物的氢化反应，以进入相应的四氢衍生物（THQ），四氢衍生物（THQs）是精细和散装化学品中存在的重要分子。在优化条件下获得了相应的THQ的近乎定量的产率。值得注意的是，各种有用的取代喹啉和其他生物学上重要的N-杂芳烃也是可行的。催化剂稳定性的提高归因于包封结构，它可以极大地减少贱金属的浸出程度并保护金属NP不会变大。