5,6,7,8-四氢喹啉-5-酮 | 53400-41-2

• 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: 5,6,7,8-四氢喹啉-5-酮
• 中文别名: 7,8-二氢-6H-喹啉-5-酮；5,6,7,8-四氢-5-喹啉酮；7,8-二氢喹啉-5(6H)-酮
• 英文名称: 5,6,7,8-tetrahydroquinolin-5-one
• 英文别名: 7,8-dihydroquinolin-5(6H)-one；7,8-dihydroquinoline-5(6H)-one；5,6,7,8-tetrahydro-5-quinolinone；5-oxo-5,6,7,8-tetrahydroquinoline；5-oxo-5H-6,7,8-trihydroquinoline；7,8-dihydro-6H-quinolin-5-one
• CAS: 53400-41-2
• 化学式: C₉H₉NO
• mdl: MFCD02181161
• 分子量: 147.177
• InChiKey: YHHBKPWMEXGLKE-UHFFFAOYSA-N

物化性质

• 沸点：
  116-117 °C(Press: 6 Torr)
• 密度：
  1.168±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免接触空气。

SDS

Material Safety Data Sheet

---

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

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5,6,7,8-Tetrahydroquinolinone-5
CAS number: 53400-41-2

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H9NO
Molecular weight: 147.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5,6,7,8-四氢喹啉-5-酮 在 lithium aluminium tetrahydride 、 ammonium acetate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 67.5h， 生成 5-(N-ethyl)amino-5,6,7,8-tetrahydroquinoline
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉 在 FeH₆Mo₆O₂₄^(3-)*3H₃N*3H⁽¹⁺⁾*7H₂O 、 双氧水 、 溴乙酸乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以60%的产率得到5,6,7,8-四氢喹啉-5-酮
  参考文献：
  名称：

  溴化物协同温和条件下 铁催化的C（sp 3）–H键的氧化功能†

  摘要：

  使用溴离子作为促进剂，可通过无机配体负载的铁催化剂和过氧化氢对CH键进行有效的氧化和官能化，从而制备相应的酮。初步的机理研究表明，溴离子可以与FeMo 6结合形成超分子形式（FeMo 6 ·2Br），可以有效地催化反应。

  DOI：

  10.1039/c9cc03939b

文献信息

• Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
  作者：Xue Li、Fang Bai、Chaogan Liu、Xiaowei Ma、Chengzhi Gu、Bin Dai

  DOI：10.1021/acs.orglett.1c02651

  日期：2021.10.1

  An efficient electrochemical method for benzylic C(sp3)–H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry

  已经开发了一种用于苄基 C(sp 3 )-H 键氧化的有效电化学方法。各种甲基芳烃、甲基杂芳烃和苄基（杂）亚甲基可以在未分割的电池中以中等至极好的收率转化为所需的芳醛和芳酮，使用 O 2作为氧源，高氯酸镥作为电解质。在循环伏安法研究、18 O 标记实验和自由基捕获实验的基础上，提出了一种可能的单电子转移机制用于电氧化反应。
• Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with <i>N</i>-Nosyl-<i>O</i>-(2-bromoethyl)hydroxylamine
  作者：Binyu Wu、Hongbing Chen、Min Gao、Xiangnan Gong、Lin Hu

  DOI：10.1021/acs.orglett.1c01091

  日期：2021.6.4

  α-aminomethylation reaction of aromatic cyclic β-keto phosphonates with N-nosyl-O-(2-bromoethyl)hydroxylamine in the presence of DBU base has been developed, affording a range of 1,3-aminoalcohols in good yields. The resultant products could be flexibly transformed into the spirocyclic and bispirocyclic azetidines via one step of Mitsunobu reaction. Mechanistic study revealed that hydroxylamine in situ generated

  在 DBU 碱存在下，芳香环 β-酮膦酸酯与N - nosyl - O-（2-溴乙基）羟胺的前所未有的串联 α-羟甲基化和 α-氨基甲基化反应被开发出来，得到了一系列 1,3-氨基醇收益良好。所得产物可以通过Mitsunobu反应一步灵活地转化为螺环和双螺环氮杂环丁烷。机理研究表明，羟胺原位生成甲醛和诺磺酰胺，进而引发连续的 Horner-Wadsworth-Emmons、Michael 和 aldol 反应。
• Heterocyclic derivatives as metabotropic glutamate receptor modulators
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP2650284A1

  公开（公告）日：2013-10-16

  The invention relates to heterocyclic derivatives of formula I as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  这项发明涉及公式I的杂环衍生物及其药学上可接受的盐。该发明还涉及制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病是有用的。
• Electrocyclization of cis-dienals in organic synthesis: a new and versatile synthetic method for the preparation of aryl- and heteroaryl-fused coumarins
  作者：Yung-Son Hon、Tze-Wei Tseng、Chia-Yi Cheng

  DOI：10.1039/b912887e

  日期：——

  Benzo-, furo-, thieno-, and pyrido[f]coumarins were prepared by generating the 2H-pyran-2-one moieties from the oxidation of the corresponding 2H-pyran rings, which were formed in situ from the electrocyclization of cis-dienals.

  通过从相应的2H-吡喃环的氧化反应生成2H-吡喃-2-酮部分来制备苯并，呋喃-，噻吩并-和吡啶并[f]香豆素，它们是由顺式C-环的电环化而形成的。日记。
• Spiro Hydantoin Aldose Reductase Inhibitors
  作者：Reinhard Sarges、Rodney C. Schnur、John L. Belletire、Michael J. Peterson

  DOI：10.1021/jm00396a037

  日期：1988.1

  formation from glucose, catalyzed by the enzyme aldose reductase, is believed to play a role in the development of certain chronic complications of diabetes mellitus. Spiro hydantoins derived from five- and six-membered ketones fused to an aromatic ring or ring system inhibit aldose reductase isolated from calf lens. In vivo these compounds are potent inhibitors of sorbitol formation in sciatic nerves of

  据信由醛糖还原酶催化的葡萄糖形成山梨醇在糖尿病的某些慢性并发症的发生中起作用。源自与芳香族环或环系统融合的五元和六元酮的螺乙内酰脲抑制从小牛晶状体分离的醛糖还原酶。在体内，这些化合物是链脲佐剂化大鼠坐骨神经中山梨醇形成的有效抑制剂。在衍生自6-卤代的2,3-二氢-4H-1-苯并吡喃-4-酮（4-苯并二氢吡喃酮）的螺旋乙内酰脲中可达到最佳的体内活性。在2,4-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷] -2'，5'-二酮中，活性仅存在于4S异构体化合物115（CP-45,634，USAN ：山梨醇）。该化合物目前正用于测试人体，