4,6,7,8-四氢-2,5(1H,3H)-喹啉二酮 | 5057-12-5

• 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 - 有机氧化合物
• 中文名称: 4,6,7,8-四氢-2,5(1H,3H)-喹啉二酮
• 中文别名: 4,6,7,8-四氢-1H，3H-喹啉-2,5-二酮；4,6,7,8-四氢-1H,3H-喹啉-2,5-二酮
• 英文名称: 4,6,7,8-tetrahydro-2,5(1H,3H)-quinolinedione
• 英文别名: 3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione；hexahydroquinoline-2,5-dione；3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinequinone；Octahydrochinolin-2,5-dion；4,6,7,8-tetrahydro-1H,3H-quinoline-2,5-dione；3,4,7,8-tetrahydro-2,5(1H,6H)-quinolinedione；3,4,5,6,7,8-hexahydrocarbostyril-5-one；1,3,4,6,7,8-hexahydroquinoline-2,5-dione
• CAS: 5057-12-5
• 化学式: C₉H₁₁NO₂
• mdl: MFCD01111799
• 分子量: 165.192
• InChiKey: KNRFNTVMEIIKEB-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于室温下，应保持干燥和密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4,6,7,8-TETRAHYDRO-1H,3H-QUINOLINE-2,5-DIONE
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: 4,6,7,8-TETRAHYDRO-1H,3H-QUINOLINE-2,5-DIONE
CAS number: 5057-12-5

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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: C9H11NO2
Molecular weight: 165.2

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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：

  4,6,7,8-四氢-2,5(1H,3H)-喹啉二酮 在 palladium on activated charcoal 盐酸 、 ruthenium trichloride 、 氢氧化钾 、 sodium hydroxide 、 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 双氧水 、 diborane(6) 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 25.0h， 生成 (4aα,5β,8aβ)-decahydroquinoline-5-carboxylic acid hydrochloride
  参考文献：
  名称：

  反式十氢喹啉-5-羧酸差向异构体的立体选择性合成。γ-氨基丁酸的非对映两性离子探针在体外和体内的相关生物学特性。

  摘要：

  描述了由乙烯基双环酰亚胺10合成反式-（4aα，8aβ）-十氢喹啉-5-羧酸（3和4）的5β和5α差向异构体。还原反式-5-（1,3-二噻-2-基）八氢-2（1H）-喹啉酮（13），得到5个α-（1,3-二噻-2-基）化合物16。 Trans-4合成的关键步骤，而硼氢化-H2O2处理苯甲基反八氢-5-亚甲基-1（2H）-喹啉羧酸酯（21）生成5β-羟甲基化合物22是关键的合成步骤。 3.研究了这些反式非对映异构体3和4以及先前制备的顺式类似物1和2与脑组织中GABAA和GABAB受体和微毒素结合位点以及神经元GABA转运系统相互作用的能力。像1和2 当将trans-3或-4给予脑室内小鼠时，会引起强直阵挛性癫痫发作。在体外，仅反式4弱抑制[3H] GABA与GABAA和GABAB受体的结合。大剂量（10 mg / kg）地西epa逆转了trans-3和trans-4的惊厥活性。尽管反式3更

  DOI：

  10.1021/jm00151a001
• 作为产物：
  描述：

  1,3-环己二酮 在 ammonium acetate 作用下， 反应 6.25h， 生成 4,6,7,8-四氢-2,5(1H,3H)-喹啉二酮
  参考文献：
  名称：

  稳定的盐酸卡替洛尔及其制法和眼用药物组 合物

  摘要：

  本发明涉及稳定的盐酸卡替洛尔及其制法和眼用药物组合物。具体的，本发明涉及一种制备盐酸卡替洛尔的方法，其包括如下步骤：制备3‑氨基‑2‑环己烯酮、制备四氢‑2,5(1H,6H)‑喹啉二酮、制备5‑羟基‑3,4‑二氢‑2(1H)‑喹诺酮、制备5‑(2,3‑环氧丙氧基)‑3,4‑二氢‑2(1H)‑喹诺酮、制备盐酸卡替洛尔。进一步的，本发明还提供了一种照本发明方法制备得到的盐酸卡替洛尔原料药，以本发明制得的盐酸卡替洛尔为原料药制备得到的眼用药物组合物，以及本发明制得的盐酸卡替洛尔在制备用于治疗或预防青光眼或高眼压症的药物中的用途。本发明方法具有优异的药学特征例如所制得的原料药和制剂具有优异的稳定性。

  公开号：

  CN107337639B

文献信息

• 3,4-Dihydrocarbostyril derivatives and process for producing the same
  申请人：OtsukaPharmaceutical Co., Ltd.

  公开号：US04256890A1

  公开（公告）日：1981-03-17

  Novel compounds represented by the formula ##STR1## wherein R.sup.1, R.sup.2, and R' and R" are defined as hereinafter, having a blocking activity on .beta.-adrenergic nerves, novel intermediates useful for synthesis thereof and processes for preparing the same are disclosed. When substitution is at the 5-position and R.sup.1 and R.sup.2 are hydrogen, R' and R" are not simultaneously hydrogen and a 1 to 4 carbon atom alkyl group in the claimed compound.

  所表示的新化合物，其分子式为##STR1##，其中R.sup.1、R.sup.2和R'以及R"的定义如下，具有阻断β-肾上腺素神经的活性，新的中间体对合成有所帮助，以及制备这些化合物的过程。当取代位置在5位且R.sup.1和R.sup.2为氢时，所申请的化合物中R'和R"不能同时为氢和1到4个碳原子的烷基团。
• Pharmaceutical compositions containing quinolin-2,5-diones, new
  申请人：Karl Thomae GmbH

  公开号：US05068334A1

  公开（公告）日：1991-11-26

  This invention relates to pharmaceutical compositions containing quinolin-2,5-diones of formula ##STR1## wherein A, B, R.sup.1 to R.sup.3 and X are defined hereinbelow, some of which are novel, which compounds have valuable pharmacological properties, particularly analgesic antipyretic and/or antiphlogistic effects, to new intermediates and processes for preparing them.

  这项发明涉及含有式##STR1##的喹啉-2,5-二酮的药物组合物，其中下文定义了A、B、R^1至R^3和X，其中一些是新颖的，这些化合物具有有价值的药理特性，特别是镇痛、退热和/或抗炎作用，以及用于制备它们的新中间体和工艺。
• 3,4-Dihydrocarbostyril derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04329468A1

  公开（公告）日：1982-05-11

  Novel compounds represented by the formula ##STR1## wherein R.sup.1, R.sup.2, R' and R" are defined as hereinafter, having a blocking activity on .beta.-adrenergic nerves, novel intermediates useful for synthesis thereof and processes for preparing the same are disclosed. When substitution is at the 5-position and R.sup.1 and R.sup.2 are hydrogen, R' and R" are not simultaneously hydrogen and a 1 to 4 carbon atom alkyl group in the claimed compound.

  本发明公开了一种由以下式子表示的新化合物：##STR1## 其中R.sup.1、R.sup.2、R'和R"的定义如下，具有对β-肾上腺素能神经的阻断活性，公开了用于合成其的新中间体以及制备它们的过程。当取代基位于5位且R.sup.1和R.sup.2为氢时，R'和R"不能同时为氢，而在所要求的化合物中为1至4碳原子烷基。
• PROCESS FOR PREPARING TETRAHYDROQUINOLONE ETHERS AND NOVEL INTERMEDIATES THEREFOR
  申请人：FUJI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0273987A1

  公开（公告）日：1988-07-13

  A process for preparing a tetrahydroquinolone ether represented by formula (i) and a novel intermediate represented by formula (VIII) for preparing said ether; wherein R' represents a straight-chain or branched alkyl group having 1 to 4 carbon atoms and R3 represents an alkylsulfonyloxy, arylsu- lfonyloxy, acyloxy or hydroxy group or a halogen atom. This process is characterized in that a 3-substituted 1,2-propylene oxide or 3-substituted 1,2-propanediol is reacted with octahydroquinoline-2,5-dione in the presence of an acid catalyst to produce a compound of the above general formula (VII), which i3 the m reacted with an alkylamine represented by the formula of R1-NH2 (wherein R' is as defined above) to produce a novel compound represented by formula (VIII),

  一种制备式(i)代表的四氢喹啉酮醚的工艺和一种制备所述醚的式(VIII)代表的新型中间体；其中R'代表具有1至4个碳原子的直链或支链烷基，R3代表烷基磺酰氧基、芳基磺酰氧基、酰氧基或羟基或卤原子。该工艺的特点是，在酸催化剂存在下，将 3-取代的 1，2-环氧丙烷或 3-取代的 1，2-丙二醇与八氢喹啉-2，5-二酮反应，生成上述通式(VII)的化合物，再与 R1-NH2（其中 R'如上定义）式所代表的烷基胺反应，生成式(VIII)所代表的新型化合物、
• Verwendung von Chinolin-2,5-dionen in einem Arzneimittel mit einer analgetischen, antipyretischen und/oder einer antiphlogistischen Wirkung
  申请人：Dr. Karl Thomae GmbH

  公开号：EP0338228A2

  公开（公告）日：1989-10-25

  Die vorliegende Erfindung betrifft Arzneimittel, enthaltend Chinolin-2,5-dione der Formel in der A, B, R₁ bis R₃ und X wie in den Ansprüchen 1 bis 6 definiert sind, sowie neue Chinolin-2,5-dione gemäß den An­sprüchen 10 bis 14, welche wertvolle pharmakologische Eigen­schaften aufweisen, insbesondere eine analgetische, antipyre­tische und/oder antiphlogistische Wirkung, neue Zwischenpro­dukte und Verfahren zu ihrer Herstellung.

  本发明涉及含有 2,5-喹啉二酮的药物，其式为 其中 A、B、R₁至 R₃和 X 如权利要求 1 至 6 所定义，以及根据权利要求 10 至 14 所述的新型喹啉-2,5-二酮，它们具有重要的药理特性，特别是镇痛、解热和/或抗血栓作用，以及制备它们的新型中间体和工艺。