5,6,7,8-四氢-8-羟基喹啉 | 14631-46-0

• 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: 5,6,7,8-四氢-8-羟基喹啉
• 中文别名: 5,6,7,8-四氢喹啉-8-醇；8-羟基-5,6,7,8-四氢喹啉
• 英文名称: 5,6,7,8-tetrahydroquinoline-8-ol
• 英文别名: 5,6,7,8-tetrahydroquinolin-8-ol；8-hydroxy-5,6,7,8-tetrahydroquinoline；5,6,7,8-Tetrahydro-8-chinolinol；1'-Hydroxy-2,3-pyrido-Δ^5'-cyclohexen
• CAS: 14631-46-0
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: YCQHYOBSOVFBEB-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  88-96 °C(Press: 2 Torr)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温密封保存，并确保干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,6,7,8-Tetrahydroquinolin-8-ol
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 5,6,7,8-Tetrahydroquinolin-8-ol
CAS number: 14631-46-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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
Not specified
Appearance:
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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (5,6,7,8-Tetrahydroquinolin-8-ol)

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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：

  5,6,7,8-四氢-8-羟基喹啉 在 4-二甲氨基吡啶 、 sodium azide 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 甲基磺酰氯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 异丙醚 、 二甲基亚砜 为溶剂， 60.0 ℃ 、2.53 MPa 条件下， 反应 41.5h， 生成 (8R)-5,6,7,8-四氢-8-氨基喹啉
  参考文献：
  名称：

  手性 8-氨基-5,6,7,8-四氢喹啉衍生物在金属催化剂中用于 1-芳基取代-3,4-二氢异喹啉作为生物碱前体的不对称转移氢化。

  摘要：

  基于 8-氨基-5,6,7,8-四氢喹啉主链的手性二胺，称为 CAMPY (L1)，或 2-甲基取代的类似物 Me-CAMPY (L2)，被用作 Cp* 金属配合物中的新型配体对于一系列取代的二氢异喹啉 (DHIQ) 的 ATH，已知是合成生物活性生物碱的关键中间体。在这种反应中评估了不同的金属基配合物，铑催化剂 C3 和 C4，证明在反应性和对映选择性方面都是最有效的。尽管获得适度的对映体过量值（在底物 I 的情况下高达 69% ee），但当 La(OTf)3 用作有益添加剂时，即使在要求最苛刻的受阻底物的情况下，也成功实现了令人满意的定量转化，

  DOI：

  10.3390/molecules28041907
• 作为产物：
  描述：

  8-羟基喹啉 在 platinum(IV) oxide 、 C₃HF₃O 、 氢气 作用下， 反应 4.0h， 生成 5,6,7,8-四氢-8-羟基喹啉
  参考文献：
  名称：

  基于 8-氨基喹啉的单功能 Pt(II) 配合物的合成和药理表征

  摘要：

  在杂环化合物中，8-氨基喹啉及其衍生物已成为制备新型抗增殖金属药物的重要候选物。在这里，我们报告了使用 8 氨基喹啉及其手性 5,6,7,8-四氢衍生物作为螯合配体的一系列铂配合物的合成和细胞毒性评估。在所提出的配合物中，使用不同且适时地烷基化的咪唑来制备相应的单官能铂配合物。对高度侵袭性的 MDA-MB-231、侵袭性和低分化三阴性乳腺癌 (TNBC) 细胞系进行了初步细胞毒性评估，为 Pt-IV 提供了显着的 IC50 10.9±1.3 μM。这一系列复合物揭示了 p53 的诱导，干扰了细胞周期 G0/G1 期的进展。

  DOI：

  10.1002/ejic.201900644

文献信息

• [EN] NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE THIÉNOPYRIMIDINE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2015097123A1

  公开（公告）日：2015-07-02

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

  式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如描述中所述。
• Chemokine receptor binding heterocyclic compounds
  申请人：AnorMED, Inc.

  公开号：US06750348B1

  公开（公告）日：2004-06-15

  This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1 to R7 may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6 alkyl; R8 is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″ group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6 alkyl group, (3) a C0-6 alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6 alkylamino or C3-7 cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.

  这项发明涉及一类新型的杂环化合物，它们结合趋化因子受体，抑制其天然配体的结合。这些化合物通过结合趋化因子受体，包括CXCR4和CCR5，从而抑制这些趋化因子的后续结合，产生对HIV感染的保护效果。本发明提供了一个式I的化合物 其中，W是氮原子，Y不存在，或者W是碳原子，Y═H； R1至R7可以相同也可以不同，并且独立地选择自氢或直链、支链或环状的C1-6烷基； R8是一个取代的杂环基或取代的芳香基 Ar是一个芳香或杂芳环，每个环在单个或多个非连接位置可选择地取代有电子给体或吸引体基团； n和n′独立地为0-2； X是下式的一个基团： 其中，环A是一个可选择地取代的饱和或不饱和的5或6元环，P是一个可选择地取代的碳原子、一个可选择地取代的氮原子、硫或氧原子。环B是一个可选择地取代的5到7元环。上述式中的环A和环B可以通过基团V从任何位置连接到基团W，其中V是一个化学键，一个(CH2)n″基团（其中n″=0-2）或一个C═O基团。Z是(1)一个氢原子，(2)一个可选择地取代的C1-6烷基基团，(3)一个用可选择地取代的芳香或杂环基团取代的C0-6烷基基团，(4)一个可选择地取代的C0-6烷基氨基或C3-7环烷氨基基团，(5)一个可选择地取代的羰基或磺酰基。这些化合物还包括任何药学上可接受的酸盐和金属络合物，以及它们的任何立体异构体形式和立体异构体形式的混合物。
• Synthesis of Enantiomerically Pure 8-Substituted 5,6,7,8-Tetrahydroquinolines
  作者：Junichi Uenishi、Masahiro Hamada

  DOI：10.1055/s-2002-23537

  日期：——

  substitution reaction with the azide, thioacetate, and dimethyl malonate anions and benzylamine gives the corresponding substituted products in an enantiomerically pure form with an inversion of the configuration in good yields. The methanolysis of (S)-5,6,7,8-tetrahydroquinolin-8-yl acetate in the presence of potassium carbonate and alkylation of the resulting thiol anion with alkyl halides in a one-pot

  对映体纯 (S)-5,6,7,8-四氢喹啉-8-醇 [(S)-1] 和 (R)-8-acetoxy-5,6,7,8-四氢喹啉 [(R)-2 ] 已经通过脂肪酶催化的外消旋 5,6,7,8-四氢喹啉-8-醇 [(')-1] 的动力学乙酰化以优异的化学产率制备。(R)-1 的甲磺酰化，然后与叠氮化物、硫代乙酸根和丙二酸二甲酯阴离子和苄胺发生取代反应，以良好的收率得到对映体纯形式的相应取代产物。(S)-5,6,7,8-四氢喹啉-8-乙酸酯在碳酸钾存在下的甲醇分解和所得硫醇阴离子与卤代烷在单锅反应中的烷基化反应得到 5,6,7 ,8-四氢喹啉-8-基硫醚。
• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• [EN] HETEROCYCLE SUBSTITUTED PYRIDINE DERIVATIVE ANTIFUNGAL AGENTS<br/>[FR] AGENTS ANTIFONGIQUES DÉRIVÉS DE PYRIDINE SUBSTITUÉS PAR UN HÉTÉROCYCLE
  申请人：AMPLYX PHARMACEUTICALS INC

  公开号：WO2019113542A1

  公开（公告）日：2019-06-13

  Described herein are heterocycle substituted pyridine derivative antifungal agents and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for the treatment of fungal diseases and infections.

  本文描述了杂环取代吡啶衍生物抗真菌药剂和包含该化合物的药物组合物。这些化合物和组合物对于治疗真菌病和感染是有用的。