5-氰基异喹啉 | 27655-41-0

• 物质功能分类: 医药中间体 - 异喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 5-氰基异喹啉
• 英文名称: isoquinoline-5-carbonitrile
• 英文别名: Isochinolin-5-carbonitril；5-Cyanoisoquinoline
• CAS: 27655-41-0
• 化学式: C₁₀H₆N₂
• mdl: MFCD03109890
• 分子量: 154.171
• InChiKey: XVJDHUCBVHTPGE-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140℃
• 沸点：
  267.53°C (rough estimate)
• 密度：
  1.1975 (rough estimate)

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：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 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：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Cyanoisoquinoline
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: 5-Cyanoisoquinoline
CAS number: 27655-41-0

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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: C10H6N2
Molecular weight: 154.2

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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：

  5-氰基异喹啉 在 盐酸 、 水 作用下， 反应 6.0h， 以84%的产率得到异喹啉-5-甲酸
  参考文献：
  名称：

  ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE

  摘要：

  从包括式(I)的异喹啉-5-羧酰胺衍生物、药用盐、异构体、水合物和溶剂化物的化合物中选择的化合物对于预防或治疗由蛋白激酶异常激活引起的与异常细胞生长相关的疾病是有效的。

  公开号：

  US20150191450A1
• 作为产物：
  描述：

  5-氨基异喹啉 在 碳酸氢钠 、 sodium nitrite 作用下， 以 盐酸 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 以56%的产率得到5-氰基异喹啉
  参考文献：
  名称：

  HIV protease inhibitors

  摘要：

  HIV蛋白酶抑制剂是通过化学合成获得的，它们可以抑制或阻断HIV蛋白酶酶的生物活性，导致HIV病毒的复制终止。这些化合物以及含有这些化合物和可选的其他抗病毒药物作为活性成分的药物组合物，适用于治疗感染HIV病毒的患者或宿主，该病毒已知会导致艾滋病。

  公开号：

  US05484926A1

文献信息

• Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
  作者：Arne Heusler、Julian Fliege、Tobias Wagener、Frank Glorius

  DOI：10.1002/anie.202104115

  日期：2021.6.14

  sensitive reagents restricts the applicability in synthetic laboratories. Herein, we report the synthesis of a broad variety of N-substituted 1,4- and 1,2-dihydropyridines by very mild and selective reduction with amine borane for the first time.

  脱芳构化是将容易获得的N-杂环转化为部分饱和基序的有效方法。二氢衍生物的操纵具有巨大的潜力，并提供了获得各种半饱和 N-杂环结构单元的途径。然而，目前的策略范围有限，敏感试剂的使用限制了合成实验室的适用性。在此，我们首次报道了通过用胺硼烷进行非常温和的选择性还原来合成多种 N-取代的 1,4- 和 1,2-二氢吡啶。
• Visible Light-Mediated Direct Decarboxylative C–H Functionalization of Heteroarenes
  作者：R. Aleyda Garza-Sanchez、Adrian Tlahuext-Aca、Ghazal Tavakoli、Frank Glorius

  DOI：10.1021/acscatal.7b01133

  日期：2017.6.2

  The direct visible light-mediated C–H alkylation of heteroarenes using aliphatic carboxylic acids is reported. This mild method proceeds at low catalyst loadings (0.5 mol %) and has a high functional group tolerance and a broad substrate scope. Notably, functionalization of (iso)quinoline, pyridine, phthalazine, benzothiazole, and other heterocyclic derivatives with both cyclic and acyclic primary

  据报道，使用脂肪族羧酸的直接可见光介导的杂芳烃的CH烷基化。这种温和的方法在低催化剂负载量（0.5摩尔％）下进行，并且具有较高的官能团耐受性和广泛的底物范围。值得注意的是，在室温下，在标准条件下，将（异）喹啉，吡啶，酞嗪，苯并噻唑和其他杂环衍生物与环状和非环状的伯，仲和叔羧酸以及氨基和脂肪酸一起官能化。该协议可以将丰富的原料快速转化为医学上相关的“类药物”部分。
• Tertiary Alcohols as Radical Precursors for the Introduction of Tertiary Substituents into Heteroarenes
  作者：Spencer P. Pitre、Mikko Muuronen、Dmitry A. Fishman、Larry E. Overman

  DOI：10.1021/acscatal.9b00405

  日期：2019.4.5

  Despite many recent advances in the radical alkylation of electron-deficient heteroarenes since the seminal reports by Minisci and co-workers, methods for the direct incorporation of tertiary alkyl substituents into nitrogen heteroarenes are limited. This report describes the use of tert-alkyl oxalate salts, derived from tertiary alcohols, to introduce tertiary substituents into a variety of heterocyclic

  尽管自Minisci和同事的开创性报道以来，在缺电子杂芳烃的自由基烷基化方面取得了许多新进展，但是将叔烷基取代基直接掺入氮杂芳烃的方法仍然受到限制。该报告描述了使用衍生自叔醇的草酸叔烷基酯盐将叔取代基引入各种杂环底物中。该反应具有相当宽的范围，在温和条件下迅速进行，并通过光化学或热活化来引发。通过闪光光解研究获得了对更高产率的可见光引发过程的潜在机制的见解，而计算研究则提供了对反应范围的见解。
• Nucleophilic trifluoromethylation of azinium salts with Zn(CF3)2·bpy
  作者：Shitao Pan、Xiu Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1016/j.tet.2021.132477

  日期：2021.11

  (Trifluoromethyl)zinc complexes have been widely used in metal-mediated trifluoromethylation reactions. However, direct nucleophilic addition with a (trifluoromethyl)zinc complex is rare. In this article, we describe an unprecedented trifluoromethylation of azinium salts using Zn(CF3)2·bpy as CF3 source, giving 1-(4-methoxybenzyl)-2-(trifluoromethyl)-1,2-dihydroquinolines as products. The latter species

  （三氟甲基）锌配合物已广泛用于金属介导的三氟甲基化反应。然而，与（三氟甲基）锌配合物的直接亲核加成很少见。在本文中，我们描述了使用 Zn(CF 3 ) 2 ·bpy 作为 CF 3源的 azinium 盐的前所未有的三氟甲基化，得到 1-(4-甲氧基苄基)-2-(三氟甲基)-1,2-二氢喹啉作为产物。后一种物质在氧化条件下进一步转化为 2-三氟甲基喹啉。这项工作还表明，配体在调节（三氟甲基）锌配合物的反应性方面起着重要作用。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXO GROUP LTD

  公开号：WO2009133136A1

  公开（公告）日：2009-11-05

  The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.

  这项发明涉及具有药理活性的新型噁二唑衍生物，其制备方法，含有它们的药物组合物以及它们在治疗各种疾病中的用途。