8-溴-1H-2-喹啉酮 | 67805-67-8

• 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: 8-溴-1H-2-喹啉酮
• 中文别名: N-丙基-N-[2-(2,4,6-三氯苯氧基)乙基]-1H咪唑-1-甲酰胺；旋保克；8-溴-2-(1H)-喹啉；8-溴喹啉-2-酮；N-丙基-N[α-(2,4,6-三氯苯氧基)乙基]-1H-咪唑-1-甲酰胺；咪鲜胺
• 英文名称: 8-bromoquinolin-2(1H)-one
• 英文别名: 8-bromo-1H-quinolin-2-one；8-bromo-1H-quinoline-2-one
• CAS: 67805-67-8
• 化学式: C₉H₆BrNO
• mdl: MFCD08741409
• 分子量: 224.057
• InChiKey: HGJBIJWBYATVQY-UHFFFAOYSA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  390.2±42.0 °C(Predicted)
• 密度：
  1.620±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Bromoquinolin-2(1H)-one
Synonyms: 8-Bromo-2-hydroxyquinoline

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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: 8-Bromoquinolin-2(1H)-one
CAS number: 67805-67-8

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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: C9H6BrNO
Molecular weight: 224.1

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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 bromide.

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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：

  8-溴-1H-2-喹啉酮 在 bis-triphenylphosphine-palladium(II) chloride 四乙基氯化铵 、 硝酸 、 铁粉 、 potassium carbonate 、 氯化铵 、 N,N-二甲基苯胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 29.5h， 生成 6-amino-8-naphthalen-1-yl-6-nitroquinoline-2-carbonitrile
  参考文献：
  名称：

  [EN] QUINOLINES AS INHIBITORS OF FARNESYL PYROPHOSPHATE SYNTHASE
  [FR] QUINOLÉINES EN TANT QU'INHIBITEURS DE LA FARNÉSYL PYROPHOSPHATE SYNTHASE

  摘要：

  本发明涉及式(I)化合物，其中取代基如说明书中所述，这些化合物作为法尼基焦磷酸合酶调节剂是有用的，例如在增殖性疾病的治疗中，涉及制造这些化合物的方法及其中间体。

  公开号：

  WO2009106586A1
• 作为产物：
  描述：

  8-溴-2-氯喹啉 在 sodium tetrachloroaurate(III) dihyrate 、 potassium tert-butylate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 21.0h， 生成 8-溴-1H-2-喹啉酮
  参考文献：
  名称：

  α-（N -2-喹啉基）酮的计算和实验评估：一类新型的非联芳基阻转异构体

  摘要：

  考虑到阻转异构体在不对称催化和药物中的有用性，已对取代的α-（N -2-喹啉基）酮进行了详尽的计算研究。这类叔酰胺是独特的，因为酰胺嵌入在芳族结构中，并且氮带有脂族取代基。使用一种计算方法，将8'-取代的喹诺酮类化合物确定为潜在的2类和3类阻转异构体靶标，其计算的C–N旋转势垒大于20 kcal / mol。报道了这些结果，以及合成这些靶标的实验性努力。

  DOI：

  10.1016/j.tetlet.2016.09.056

文献信息

• Fe and Co Complexes of Rigidly Planar Phosphino-Quinoline-Pyridine Ligands for Catalytic Hydrosilylation and Dehydrogenative Silylation
  作者：Debashis Basu、Ryan Gilbert-Wilson、Danielle L. Gray、Thomas B. Rauchfuss、Aswini K. Dash

  DOI：10.1021/acs.organomet.8b00416

  日期：2018.8.27

  of simple and complex 1-alkenes with a variety of hydrosilanes. Catalysts derived from MesNQpy exhibited low activity. Fe-RPQpy derived catalysts favor hydrosilylation, whereas Co-RPQpy based catalysts favor dehydrogenative silylation. Catalysts derived from CoX2(iPrPQpy) convert hydrosilanes and ethylene to vinylsilanes. Related experiments were conducted on propylene to give propenylsilanes.

  制备了一种新的刚性平面PNN配体平台的Co和Fe二卤化物配合物，并将其作为烯烃氢化硅烷化的预催化剂。将Thummel的8-溴-2-（吡啶-2'-基）喹啉锂化，然后用（i- Pr）2 PCl和（C 6 F 5）2 PCl处理，得到膦-喹啉-吡啶配体，缩写为R PQpy对于R ＝i- Pr和C 6 F 5。这些配体与铁和钴的二氯化物和二溴化物形成1：1加合物。FeBr 2（iPr PQpy），FeBr 2（ArFPQpy），CoCl 2（iPr PQpy），CoBr 2（iPr PQpy）和CoCl 2（ArF PQpy）证实这些配合物的M–P–C–C–N–C–C–N部分在0.078范围内为平面不同于前几代的PNN配合物，其平面度偏差约为0.35。键距和磁性表明Fe络合物为高自旋，而钴络合物为高自旋或参与自旋平衡。还研究了R PQpy配体的NNN类似物，其中膦基被异丁烯酮取代。FeBr 2（Mes
• [EN] AMIDES AS PIM INHIBITORS<br/>[FR] AMIDES CONVENANT COMME INHIBITEURS DES PIM
  申请人：AMGEN INC

  公开号：WO2013130660A1

  公开（公告）日：2013-09-06

  The invention relates to amide-containing compounds of formula (1), and salts thereof. In some embodiments, the invention relates to inhibitors or modulators of Pim-1 and/or Pim-2, and/or Pim-3 protein kinase activity or enzyme function. In still further embodiments, the invention relates to pharmaceutical compositions comprising compounds disclosed herein, and their use in the prevention and treatment of Pim kinase related conditions and diseases, preferably cancer.

  本发明涉及式(1)的含酰胺化合物及其盐。在一些实施例中，本发明涉及Pim-1和/或Pim-2和/或Pim-3蛋白激酶活性或酶功能的抑制剂或调节剂。在更进一步的实施例中，本发明涉及包含本文披露的化合物的药物组合物，及其用于预防治疗Pim激酶相关状况和疾病，尤其是癌症的应用。
• Noncovalent Interactions in Ir-Catalyzed C–H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
  作者：Md Emdadul Hoque、Ranjana Bisht、Chabush Haldar、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.7b04490

  日期：2017.6.14

  An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented

  描述了一种用于芳族酯的对位选择性硼化的有效策略。为了获得高的对位选择性，已经开发了一种新的催化体系，该体系改变了联吡啶的核心结构。有人提出，L型配体对于通过非共价相互作用识别酯羰基的氧原子的功能至关重要，这为超选择性C–H活化/硼化提供了空前的控制因素。
• Compounds
  申请人：Cailleau Nathalie

  公开号：US20080221110A1

  公开（公告）日：2008-09-11

  Tricyclic nitrogen containing compounds and their use as antibacterials

  三环氮含化合物及其作为抗菌剂的用途
• Scalable and Practical Synthesis of Halo Quinolin-2(1<i>H</i>)-ones and Quinolines
  作者：Cornelia Zaugg、Gunther Schmidt、Stefan Abele

  DOI：10.1021/acs.oprd.7b00124

  日期：2017.7.21

  A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28–93% yield (2 steps). The

  提出了一种实用且可扩展的卤代喹啉-2（1 H）-one合成方法。杂环很容易从廉价的卤代苯胺中以两步顺序进入。在碱性条件下，苯胺用3,3-二甲氧基丙酸甲酯以定量收率酰化。粗制酰胺在硫酸中环化成所需的卤代喹啉-2（1 H）-1，产率为28-93％（2步）。合成序列已成功应用于800 g规模。具有强吸电子基团或给电子基团的苯胺对于该方法而言是较差的底物。将6-碘喹啉-2（1H）-1和6-溴-8-碘喹啉-2（1H）-1进一步官能化以获得被各种官能团取代的喹啉。