2-苯基咪唑并[1,2-a]吡啶-3-甲醛 | 3672-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基咪唑并[1,2-a]吡啶-3-甲醛
• 中文别名: 2-苯基咪唑并[1,2-A]吡啶-3-甲醛
• 英文名称: 2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 3672-39-7
• 化学式: C₁₄H₁₀N₂O
• mdl: MFCD00964691
• 分子量: 222.246
• InChiKey: GDQWGRMPXASNTI-UHFFFAOYSA-N

物化性质

• 溶解度：
  >33.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 储存条件：
  存储条件：2-8°C，密封，干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde
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: 2-Phenyl-imidazo[1,2-a]pyridine-3-carbaldehyde
CAS number: 3672-39-7

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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: C14H10N2O
Molecular weight: 222.2

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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：

  2-苯基咪唑并[1,2-a]吡啶-3-甲醛 在 叔丁基过氧化氢 、 碘 作用下， 以 水 、 乙腈 为溶剂， 以82%的产率得到3-iodo-2-phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Metal-free oxidative decarbonylative halogenation of fused imidazoles

  摘要：

  已经开发出一种高效策略，用于在温度控制下，在TBHP存在的情况下对卡巴醛咪唑融合杂环进行脱甲酰卤代反应。

  DOI：

  10.1039/d1nj04440k
• 作为产物：
  描述：

  2-苯基咪唑并[1,2-a]吡啶 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 以73%的产率得到2-苯基咪唑并[1,2-a]吡啶-3-甲醛
  参考文献：
  名称：

  咪唑并吡啶Oxindole缀合物的合成及生物评价作为微管靶向剂。

  摘要：

  合成了咪唑并吡啶-羟吲哚缀合物文库，并研究了其对多种人类癌细胞系的抗癌活性。一些测试化合物，如10，10e中，10f中，与10千，表现出有前途的抗增殖活性与GI 50值的范围为0.17〜9.31μ中号。流式细胞仪分析表明，用这些化合物处理的MCF-7细胞以浓度依赖的方式停滞在细胞周期的G 2 / M期。更特别地，化合物10f对微管蛋白聚合显示出显着的抑制作用。所有这些化合物使线粒体膜电位去极化并引起细胞凋亡。这些结果进一步证实了Ser473处Akt的磷酸化降低。胚胎发育研究表明，铅化合物10 f和10 k导致斑马鱼胚胎发育延迟。化合物10 f与微管蛋白的对接表明，咪唑并[1,2- a ]吡啶部分占据了微管蛋白的秋水仙碱结合位点。

  DOI：

  10.1002/cmdc.201300308

文献信息

• Synthesis of functionalized chromene and spirochromenes using l -proline-melamine as highly efficient and recyclable homogeneous catalyst at room temperature
  作者：Sakkani Nagaraju、Banoth Paplal、Kota Sathish、Santanab Giri、Dhurke Kashinath

  DOI：10.1016/j.tetlet.2017.09.060

  日期：2017.11

  commercially cheap l-proline and melamine for the synthesis of chromenes and spirochromenes (spirooxindoles) via multicomponent reactions at room temperature. Systematic studies were conducted in order to achieve desired reactivity and recyclability of the catalyst using various α-amino acids and aromatic amines as donor-acceptor pairs. Among the screened combinations, l-proline and melamine (3:1 ratio;

  使用便宜的1-脯氨酸和三聚氰胺开发了一种有效且可循环使用的均相催化剂，用于在室温下通过多组分反应合成色烯和螺环色酮（螺并辛多烯）。为了使用各种α-氨基酸和芳族胺作为供体-受体对，进行系统研究以实现所需的反应性和催化剂的可回收性。在筛选的组合中，l脯氨酸和三聚氰胺（3：1的比例；占总重量的3 mol％）被认为是最佳的催化剂，可以在室温下非常短的时间内（1-15分钟）以优异的产率（高达99％）提供所需的产品在DMSO中作为溶剂。通过添加EtOAc来回收催化剂，并且在不损失催化活性的情况下重复使用多达5个循环。
• Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of <i>tert</i>-butyl hydroperoxide as both an oxidant and a methylene source
  作者：Om P. S. Patel、Nitesh Kumar Nandwana、Ajay Kumar Sah、Anil Kumar

  DOI：10.1039/c8ob02432d

  日期：——

  A metal-free method is developed for the aminomethylation of imidazoheterocycles with 2/4-aminoheterocycles using TBHP as a carbon source as well as an oxidant.

  以 TBHP 为碳源和氧化剂，开发了一种咪唑杂环与 2/4- 氨基杂环进行氨基甲基化的无金属方法。
• H₂O₂/DMSO-Promoted Regioselective Synthesis of 3,3′-Bisimidazopyridinylmethanes via Intermolecular Oxidative C(sp²)–H Bond Activation of Imidazoheterocycles
  作者：Om P. S. Patel、Devireddy Anand、Rahul K. Maurya、Prem P. Yadav

  DOI：10.1021/acs.joc.6b01355

  日期：2016.9.2

  under air. A library of 3,3′-bis(2-arylimidazo[1,2-a]pyridin-3-yl)methanes has been achieved in good to excellent yields. The present methodology has been successfully applied to imidazo[2,1-b]thiazoles and imidazo[2,1-b]benzothiazoles. Furthermore, the current approach was also extended for the synthesis of unsymmetrical 3,3′-bisimidazopyridinylmethanes under optimized reaction conditions. A mechanistic

  在过去的十年中，无金属的C–C键形成方法因其易用性和低成本而备受关注。该报告代表了一种新的，无金属的3,3'-双咪唑并吡啶甲基甲烷的合成方法，该方法是通过咪唑并[1,2- a ]吡啶的分子间氧化C（sp 2）-H键分子间氧化，并以二甲基亚砜作为碳合成子（CH 2）在空气中使用H 2 O 2作为温和的氧化剂。已经获得了3,3'-双（2-芳基咪唑并[1,2- a ]吡啶-3-基）甲烷的文库，收率良好至极佳。本方法已成功地应用于咪唑并[2,1- b ]噻唑和咪唑并[2,1- b]苯并噻唑。此外，当前的方法也扩展到在优化的反应条件下合成不对称的3,3'-双咪唑并吡啶基甲烷。根据自由基清除剂的实验，DMSO- d 6和ESI-MS的观察结果，提出了一种机理途径。
• Synthesis of Indolizines via Reaction of 2-Substitued Azaarenes with Enals by an Amine-NHC Relay Catalysis
  作者：Hongxian Li、Xiangmin Li、Yang Yu、Jianjun Li、Yuan Liu、Hao Li、Wei Wang

  DOI：10.1021/acs.orglett.7b00566

  日期：2017.4.21

  A metal-free catalytic strategy for the facile synthesis of biologically relevant molecular architectures indolizines and imidazopyridines has been developed. The process is promoted by amine and N-heterocyclic carbene (NHC) relay catalysis via Michael addition-[3 + 2] fusion of simple azaarenes and α,β-unsaturated aldehydes. The preparative power is demonstrated in the synthesis of anxiolytic drug

  已经开发了一种无金属催化策略，用于轻松合成生物学相关的分子结构吲哚嗪和咪唑并吡啶。胺和N-杂环卡宾（NHC）中继催化通过简单的氮杂芳烃和α，β-不饱和醛的Michael加成-[3 + 2]融合促进了该过程。通过两次简单的一锅操作合成抗焦虑药物沙立肽，证明了制备能力，总收率达45％。
• CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines
  作者：Jaideep B. Bharate、Sheenu Abbat、Prasad V. Bharatam、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1039/c5ob00776c

  日期：——

  Copper bromide catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes provides direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines.

  铜溴化物催化的氧化偶联反应将2-氨基吡啶与肉桂醛直接偶联，可直接合成3-甲醛基-2-苯基咪唑并[1,2-a]吡啶。