2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐 | 766545-20-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐
• 中文别名: 2-氯-5,6,7,8-四氢-1,6-二氮杂萘盐酸盐；2-氯-5,6,7,8-四氢-1,6-萘啶
• 英文名称: 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride
• 英文别名: 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine;hydrochloride
• CAS: 766545-20-4
• 化学式: C₈H₉ClN₂*ClH
• 分子量: 205.087
• InChiKey: FRACHJCOMOVESL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  24.9
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,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: 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine, HCl
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: 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine, HCl
CAS number: 766545-20-4

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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: C8H9ClN2.ClH
Molecular weight: 205.1

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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 chloride.

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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

用途

1,6-萘啶是二氮杂萘化合物中研究最为广泛的一种。它由两个含氮杂原子的芳香稠环组成，具有特殊的刚性平面结构，表现出良好的光物理和光化学性质，因此在有机发光材料、光电器件、荧光化学传感器、有机分子催化反应以及配位化学等领域有着广泛的应用。随着对1,6-萘啶研究的不断深入，在其环上引入多种不同基团形成的衍生物能够与生物小分子或金属离子作用，并具有可控的光物理性质。特别是某些1,6-萘啶衍生物表现出良好的生理活性，已被临床应用于治疗特定疾病。

制备

1,6-萘啶可通过取代甲酸三乙酯在碱性条件下进行关环反应制备，再经氢化还原获得目标产物。具体步骤如下：

图1展示了2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐的合成反应式。

在100毫升圆底烧瓶中加入2-羟基-5,6,7,8-四氢-1,6-萘啶和过量的三氯氧磷。可选择添加无水氯化铁或四甲基哌啶氮氧化物作为自由基抑制剂，并在氮气保护下加热回流反应。当三氯氧磷溶解开始反应，直至变为黑色黏稠液体时，即表明反应结束。通过薄层色谱检测反应进度。

冷却至室温后，将反应液倒入含有少量碎冰的烧杯中，并用浓氨水调节pH值至中性，从而析出大量褐色固体。过滤除去不溶物并干燥得粗产物。随后，利用柱层析硅胶进行分离纯化，淋洗剂为二氯甲烷与石油醚体积比1:10的混合液，最终得到目标产物2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐。

反应信息

• 作为反应物：
  描述：

  2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐 在 tris-(dibenzylideneacetone)dipalladium(0) 盐酸 、 sodium methylate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 6.5h， 生成 AMG 925
  参考文献：
  名称：

  FUSED TRICYCLIC DUAL INHIBITORS OF CDK 4/6 AND FLT3

  摘要：

  Formula I的化合物是CDK 4、CDK6和FLT3的有效抑制剂。这些化合物在治疗癌症和其他各种疾病条件方面非常有用。Formula I的化合物具有以下结构：其中R1是Formula IA、Formula IB、Formula IC或Formula ID的一个基团，其他变量的定义在此处提供。

  公开号：

  US20120244110A1
• 作为产物：
  描述：

  6-苄基-5,6,7,8-四氢-1,6-萘啶-2(1H)-酮 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 2-氯-5,6,7,8-四氢-1,6-萘啶盐酸盐
  参考文献：
  名称：

  Compounds and methods of use

  摘要：

  根据以下公式（I）提供化合物： 及其药学上可接受的盐，以及其药物组合物；其中X1、X2、X3、X4、Y、A、L1、L2、R1、R2、R5、m和n如本文所定义。本发明的化合物被认为对预防和治疗各种疾病条件有用。

  公开号：

  US11077101B1

文献信息

• Substituted 4-amino[1,2,4]triazolo[4,3-a] quinoxalines
  申请人：Pfizer Inc.

  公开号：US20040192698A1

  公开（公告）日：2004-09-30

  The present invention provides compounds of formula (I) 1 the prodrugs thereof, and the pharmaceutically acceptable salts of the compounds and prodrugs, wherein R a , R b , R 1 , and R 2 are as defined herein; pharmaceutical compositions thereof; and uses thereof.

  本发明提供了式(I)的化合物 1 的前药，以及所述化合物和前药的药学上可接受的盐，其中R a ，R b ，R 1 和R 2 如本文所定义；其药物组合物；以及其用途。
• [EN] TETRAHYDRONAPHTHYRIDINES AND AZA DERIVATIVES THEREOF AS HISTAMINE H3 RECEPTOR ANTAGONISTS<br/>[FR] TÉTRAHYDRONAPHTHYRIDINES ET SES DÉRIVÉS AZA À TITRE D'ANTAGONISTES DES RÉCEPTEURS D'HISTAMINE H3
  申请人：EVOTEC NEUROSCIENCES GMBH

  公开号：WO2009121812A1

  公开（公告）日：2009-10-08

  The invention relates to compounds of formula (I), wherein X1a, X1 to X5, Ra, Rb, n and R have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

  该发明涉及式(I)的化合物，其中X1a，X1至X5，Ra，Rb，n和R的含义如描述和权利要求中所述。所述化合物可用作组胺H3受体拮抗剂。该发明还涉及药物组合物，以及制备此类化合物的方法，以及作为药物的生产和使用。
• [EN] AZETIDINES AND CYCLOBUTANES AS HISTAMINE H3 RECEPTOR ANTAGONISTS<br/>[FR] AZÉTIDINES ET CYCLOBUTANES COMME ANTAGONISTES DES RÉCEPTEURS H3 DE L'HISTAMINE
  申请人：EVOTEC NEUROSCIENCES GMBH

  公开号：WO2009135842A1

  公开（公告）日：2009-11-12

  The invention relates to compounds of formula (I) wherein R, R0, R1, m, n and X1 to X4 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antagonists. The invention also relates to pharmaceutical compositions, the preparation of such compounds as well as the production and use as medicament.

  本发明涉及具有式(I)的化合物，其中R，R0，R1，m，n和X1至X4如描述和权利要求中所引述的含义。所述化合物作为组胺H3受体拮抗剂是有用的。本发明还涉及药物组合物，以及此类化合物的制备以及作为药品的生产和使用。
• [EN] SUBSTITUTED 2H-[1,2,4]TRIAZOLO[4,3-A]PYRAZINES AS GSK-3 INHIBITORS<br/>[FR] 2H-[1,2,4]TRIAZOLO[4,3-A]PYRAZINES SUBSTITUEES EN TANT QU'INHIBITEURS DE LA GSK-3
  申请人：PFIZER PROD INC

  公开号：WO2005035532A1

  公开（公告）日：2005-04-21

  The invention relates to compounds of formula (I) prodrugs thereof, and the pahrmaceutically acceptabel salts of the compounds and prodrugs, wherein Ra, Rb, R1 and R2 are as defined herein; pharmaceutical compositions thereof; and uses thereof.

  这项发明涉及到式(I)化合物及其前药，以及该化合物和前药的药用可接受盐，其中Ra、Rb、R1和R2如本文所定义；药物组合物；以及它们的用途。
• [EN] SUBSTITUTED 1,1'-BIPHENYL COMPOUNDS AND METHODS USING SAME<br/>[FR] COMPOSÉS 1,1'-BIPHÉNYLE SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ARBUTUS BIOPHARMA INC

  公开号：WO2021158481A1

  公开（公告）日：2021-08-12

  The present invention includes substituted 1,1'-biphenyl compounds, analogues thereof, and compositions comprising the same. In one aspect, the compounds contemplated in the invention can be used to treat, ameliorate, or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient. In another aspect, the compounds contemplated in the invention can be used to treat, ameliorate, and/or prevent cancer in a patient.

  本发明包括取代的1,1'-联苯化合物，其类似物，以及包含它们的组合物。在一个方面，本发明中考虑的化合物可用于治疗、改善或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。在另一个方面，本发明中考虑的化合物可用于治疗、改善和/或预防患者体内的癌症。