6-氰基异喹啉 | 106778-42-1

• 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: 6-氰基异喹啉
• 中文别名: 6-异喹啉甲腈
• 英文名称: isoquinoline-6-carbonitrile
• 英文别名: 6-cyanoisoquinoline
• CAS: 106778-42-1
• 化学式: C₁₀H₆N₂
• mdl: MFCD09991660
• 分子量: 154.171
• InChiKey: DCSWGUBEMVRKQO-UHFFFAOYSA-N

物化性质

• 沸点：
  341.5±15.0 °C(Predicted)
• 密度：
  1.21±0.1 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 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: 6-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: 6-Cyanoisoquinoline
CAS number: 106778-42-1

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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：

  6-氰基异喹啉 在 盐酸 作用下， 以82 %的产率得到6-异喹啉甲酸
  参考文献：
  名称：

  AKT 氨基噻二唑抑制剂的结构优化

  摘要：

  我们在此报告了一系列新型 AKT 激酶抑制剂的发现和结构引导优化。基于对2的预测活性结合构象的对接研究，开发了一系列有效的N-取代-5-(异喹啉-6-基)-1,3,4-噻二唑-2-胺。该系列中的化合物在癌细胞中实现了 AKT 通路抑制，这是通过抑制通路蛋白 pGSK 和 pFKHR 来衡量的。在荷瘤小鼠的单剂量 PK/PD 体内研究中进一步评估了化合物12 ，并证明了对直接底物 GSK 和途径生物标志物 S6 的磷酸化的抑制。

  DOI：

  10.1007/s00044-023-03072-4
• 作为产物：
  描述：

  在 nickel(II) iodide 、 三甲基溴硅烷 、 三(三甲基硅基)硅烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 17.0h， 生成 6-氰基异喹啉
  参考文献：
  名称：

  芳基卤化物的光化学启用的镍催化氰化

  摘要：

  报道了使用 1,4-二氰基苯作为氰化剂的光促进 Ni 催化的芳基卤化物氰化反应。广泛的芳基溴化物、氯化物和药物样分子可以转化为相应的腈（65 个例子）。机理研究表明，在辐照下，氧化加成产物 Ni(II)(dtbbpy)( p -C 6 H 4 CN)(CN) 发生 Ni-芳基键均裂，生成芳基自由基和 Ni(I) -CN 物质，后者引发随后的氰化反应。

  DOI：

  10.1021/acs.orglett.2c00203

文献信息

• Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith
  申请人：D'Sidocky Neil R.

  公开号：US20080242694A1

  公开（公告）日：2008-10-02

  Provided herein are Heterocyclic Compounds having the following structure: wherein R 1 , R 2 , X, Y and Z are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heterocyclic Compound to a patient in need thereof.

  本文提供具有以下结构的杂环化合物： 其中R1、R2、X、Y和Z如本文所定义，包含有效量杂环化合物的组合物，以及治疗或预防癌症、炎症性疾病、免疫疾病、代谢性疾病以及通过给予患者需要的有效量杂环化合物来抑制激酶途径治疗或预防的疾病的方法。
• Direct Arylation of Unactivated Alkanes with Heteroarenes by Visible-Light Catalysis
  作者：Cheng Huang、Jing-Hao Wang、Jia Qiao、Xiu-Wei Fan、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.joc.9b01603

  日期：2019.10.18

  we describe the successful arylation of unactivated alkanes with heteroarenes by using iridium polypyridyl complexes as the photocatalyst and persulfate as the HAT catalyst precursor under visible-light irradiation. This reaction features good functional group tolerance and broad scope with regard to both alkane and heteroarene substrates (37 examples), which allows direct access to alkyl-substituted

  脂肪族CH键的官能化既是有机合成中的主要挑战，也是理想的目标。在这里，我们描述了通过使用铱多吡啶基配合物作为光催化剂，过硫酸盐作为HAT催化剂前体在可见光照射下成功地将未活化的烷烃与杂芳烃芳基化。该反应对烷烃和杂芳烃底物均具有良好的官能团耐受性和广泛的适用范围（37个实例），可直接使用烷基取代的N-杂芳烃，这是天然产物和生物活性分子的关键结构基序。
• 5-碘异喹啉类化合物的高收率合成方法
  申请人：常州工学院

  公开号：CN112300072A

  公开（公告）日：2021-02-02

  本发明涉及5‑碘异喹啉类化合物的高收率合成方法，将异喹啉类化合物、N‑碘代丁二酰亚胺以及酸液在氮气气氛下于反应温度‑5℃以下搅拌反应1h～5h，反应结束后，加入碱液搅拌以淬灭反应，经过后处理得到5‑碘异喹啉类化合物；其中所述异喹啉类化合物为异喹啉、烷基取代异喹啉或卤素取代异喹啉。本发明方法能够高效高收率制得5‑碘异喹啉类化合物，本发明方法的5位碘取代产物收率在80wt％以上，即使是在中试过程中5‑碘异喹啉类化合物产物的收率仍在75wt％以上，具有较大的工业应用价值，适于工业化批量生产。
• Chemoselective N–H functionalization of indole derivatives <i>via</i> the Reissert-type reaction catalyzed by a chiral phosphoric acid
  作者：Yue Cai、Qing Gu、Shu-Li You

  DOI：10.1039/c8ob01863d

  日期：——

  An asymmetric N-alkylation of indole derivatives via the Reissert-type reaction was realized in the presence of a catalytic amount of chiral phosphoric acid. Various enantioenriched indoles with N-1 substituted by 1,2-dihydroisoquinoline could be obtained under mild conditions in good yields and enantioselectivities at room temperature (up to 98% yield, 94% ee). The current method is compatible with

  在催化量的手性磷酸的存在下，通过Reissert型反应实现了吲哚衍生物的不对称N-烷基化。在温和的条件下，可以在室温下以良好的收率和对映选择性（高达98％的收率，94％ee）获得各种被1，2-二氢异喹啉取代的N -1的对映体富集的吲哚。当前的方法与克级反应兼容，并且产物可以进行多种化学转化。
• 氮杂环类衍生物、其制备方法及其医药用途
  申请人：北京越之康泰生物医药科技有限公司

  公开号：CN109232533A

  公开（公告）日：2019-01-18

  本发明涉及一种氮杂环类衍生物、其制备方法及其医药用途。特别地，本发明涉及通式(I)所示的氮杂环类衍生物、其制备方法、含有该衍生物的药物组合物，以及其作为SMO拮抗剂，特别是在治疗与Hedgehog信号通路相关的疾病如癌症中的用途。其中通式(I)中的各基团的定义与说明书中的定义相同。