1,2,3,4-四氢喹啉-5-胺 | 36887-98-6

• 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: 1,2,3,4-四氢喹啉-5-胺
• 英文名称: 1,2,3,4-tetrahydroquinolin-5-amine
• 英文别名: 5-amino-1,2,3,4-tetrahydroquinoline
• CAS: 36887-98-6
• 化学式: C₉H₁₂N₂
• 分子量: 148.208
• InChiKey: WOHCILOGDCVXRE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±31.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C，需充气并避免光照。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,2,3,4-Tetrahydroquinolin-5-amine
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: 1,2,3,4-Tetrahydroquinolin-5-amine
CAS number: 36887-98-6

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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, refrigerated.
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: C9H12N2
Molecular weight: 148.2

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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：

  1,2,3,4-四氢喹啉-5-胺 在 potassium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  作用于 Asp375 ​​的基于 5-氨基四氢喹啉的 LSD1 抑制剂的设计、合成和生物学评价

  摘要：

  赖氨酸特异性组蛋白去甲基化酶 1 (LSD1) 的异常表达与不同的癌症类型有关，LSD1 抑制活性似乎在癌症治疗中具有很高的治疗潜力。在这里，我们报告了基于 5-氨基四氢喹啉的新型 LSD1 抑制剂的设计、合成和生化评估。其中，化合物A6、A8、B1 - B5和C4对LSD1显示出较好的抑制作用，IC 50 = 0.19–0.82 µM。选择了几种有效的化合物来评估它们对 LSD1 高表达的 A549 细胞和 MCF-7 细胞的抗增殖活性。通过分子对接揭示了化合物的潜在结合模式，以合理化化合物对 LSD1 的效力。我们的数据认识到，5-氨基四氢喹啉支架可作为开发用于癌症治疗的有效 LSD1 抑制剂的起点。

  DOI：

  10.1002/ardp.202100102
• 作为产物：
  描述：

  5-氨基喹啉 在 二乙基硅烷 、 三(五氟苯基)硼烷 、 盐酸 作用下， 以 氯仿 、 乙醚 为溶剂， 反应 13.0h， 以84%的产率得到1,2,3,4-四氢喹啉-5-胺
  参考文献：
  名称：

  用氢硅烷将取代的喹啉氢化还原为四氢喹啉

  摘要：

  通过使用氢硅烷作为还原剂，开发了一种无金属氢化还原取代的 N-杂芳烃的方法。优化条件成功应用于喹啉、喹喔啉和喹啉N-氧化物的反应。它们对于还原带有氨基或羟基的喹啉也很有效，其中 H2 是通过胺或羟基部分的脱氢甲硅烷基化而产生的。初步的机理研究表明，催化循环的第一步是将氢硅烷 1,4-加成到喹啉中，得到 1,4-二氢喹啉；随后进行（转移）氢化以提供作为最终产品的四氢喹啉。

  DOI：

  10.1055/s-0036-1588442

文献信息

• Rhodium catalyzed hydrogenation of nitrogen heteroaromatics under water gas shift conditions. Selective synthesis of 1,2,3,4-tetrahydroquinolines and -formyl-1,2,3,4-tetrahydroisoquinolines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Yoshiaki Hirai

  DOI：10.1016/s0040-4039(00)95653-3

  日期：1987.1

  Quinolines and isoquinolines are hydrogenated selectively in the nitrogen-containing ring by means of carbon monoxide and water in the presence of catalytic amount of rhodium carbonyl cluster.

  在催化量的羰基铑簇存在下，借助一氧化碳和水在含氮环中将喹啉和异喹啉选择性氢化。
• Rhodium Catalyzed Hydrogenation of Quinolines and Isoquinolines under Water-Gas Shift Conditions
  作者：Shun-Ichi Murahashi、Yasushi Imada、Yoshiaki Hirai

  DOI：10.1246/bcsj.62.2968

  日期：1989.9

  Wide variety of quinolines and isoquinolines can be hydrogenated selectively in the nitrogen-containing ring by means of carbon monoxide and water in the presence of catalytic amount of rhodium carbonyl cluster. These reactions provide a useful method for the preparation of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydroisoquinolines which are key intermediates for the synthesis of isoquinoline

  在催化量的铑羰基簇的存在下，通过一氧化碳和水可以在含氮环中选择性地氢化多种喹啉和异喹啉。这些反应为制备 1,2,3,4-四氢喹啉和 1,2,3,4-四氢异喹啉提供了一种有用的方法，它们是合成异喹啉生物碱和其他生物活性氮化合物的关键中间体。
• Metal-free Reduction of Nitro Aromatics to Amines with B2(OH)4/H2O
  作者：Haifeng Zhou、Yasuhiro Uozumi、Danyi Chen、Yanmei Zhou、Sensheng Liu、Qixing Liu、Kaili Zhang

  DOI：10.1055/s-0037-1610086

  日期：2018.8

  A metal-free reduction of nitro aromatics mediated by di­boronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.

  已经开发出一种由二硼酸在温和条件下用水作为氢供体和溶剂介导的硝基芳烃的无金属还原。以良好的官能团耐受性和良好的收率获得了一系列芳香胺。
• [EN] 4-SUBSTITUTED 4, 6-DIALKOXY-CINNOLINE DERIVATIVES AS PHOSPODIESTERASE 10 INHIBITORS FOR THE TREATMENT OF PSYCHIATRIC OR NEUROLOGICAL SYNDROMS<br/>[FR] DERIVES DE 4, 6-DIALKOXY-CINNOLINE SUBSTITUES EN POSITION 4 EN TANT QU'INHIBITEURS DE PHOSPODIESTERASE 10 POUR LE TRAITEMENT DE SYNDROMES PSYCHIATRIQUES OU NEUROLOGIQUES
  申请人：MEMORY PHARM CORP

  公开号：WO2006028957A1

  公开（公告）日：2006-03-16

  The present disclosure relates generally to the field of phosphodiesterase 10 (PDE10) enzyme inhibition by cinnoline compounds of Formulas: (I) and (II); wherein R'-R3 and R15-R18 are as defined herein. Still further, the present invention provides methods for synthesizing compounds with such activity and selectivity, as well as methods of and corresponding pharmaceutical compositions for treating a patient, e.g., mammals, including humans, in need of PDE inhibition. Treatment is preferably for a disease state that involves elevated intracellular PDE10 levels or decreased cAMP and/or cGMP levels, e.g., involving neurological or psychiatric syndromes, especially those states associated with psychoses, most especially schizophrenia or bipolar disorder, obsessive-compulsive disorder, and/or Parkinson’s disease. In particular, such psychoses, obsessive-compulsive disorder, and/or Parkinson’s disease are due at least in part to catabolism of intracellular cAMP and/or cGMP levels by PDE10 enzymes or where such an impaired condition can be improved by increasing cAMP and/or cGMP levels.

  本公开涉及磷酸二酯酶10（PDE10）酶被Formula（I）和（II）的喹啉类化合物抑制；其中R'-R3和R15-R18如本文所定义。此外，本发明提供了合成具有此类活性和选择性的化合物的方法，以及用于治疗需要PDE抑制的患者，例如哺乳动物，包括人类的方法和相应的药物组合物。治疗最好用于涉及细胞内PDE10水平升高或cAMP和/或cGMP水平降低的疾病状态，例如涉及神经系统或精神症候群，尤其是与精神病、强迫症、帕金森病有关的状态。特别是这些精神病、强迫症和/或帕金森病至少部分是由PDE10酶分解细胞内cAMP和/或cGMP水平引起的，或者这种受损状态可以通过增加cAMP和/或cGMP水平来改善。
• Continuous and Selective Hydrogenation of Heterocyclic Nitroaromatics in a Micropacked Bed Reactor
  作者：Xiaonan Duan、Xuepeng Wang、Xingkun Chen、Jisong Zhang

  DOI：10.1021/acs.oprd.1c00164

  日期：2021.9.17

  selective hydrogenation of heterocyclic nitroaromatics and the reductions of 5-nitroisoquinoline to 5-aminoisoquinoline and 5-amino-1,2,3,4-tetrahydroisoquinoline are selected as the model reactions. With the optimal reaction conditions, maximal yields of 99.9% (5-aminoisoquinoline) and 99.3% (5-amino-1,2,3,4-tetrahydroisoquinoline) are obtained successfully. Moreover, this system exhibits remarkable performance

  杂环硝基芳烃的加氢在制药工业中对关键中间体的合成具有重要意义。然而，传统间歇式反应器回混严重，传质性能差，难以实现高选择性，对后续的分离过程提出了很高的要求。在这项工作中，开发了一种基于微填充床反应器的连续流动系统，用于杂环硝基芳烃的选择性加氢，并选择将 5-硝基异喹啉还原为 5-氨基异喹啉和 5-氨基-1,2,3,4-四氢异喹啉作为模型反应。在最佳反应条件下，成功获得了99.9%（5-氨基异喹啉）和99.3%（5-氨基-1,2,3,4-四氢异喹啉）的最大产率。而且，该系统对相关杂环硝基芳烃的选择性加氢表现出卓越的性能，收率均超过97.5%。与间歇式反应器相比，连续流动系统能够实现杂环硝基芳烃的高效加氢和显着的目标产物选择性，反应时间更短，操作更安全。