6-甲基咪唑并[1,2-a]吡啶-3-甲醛 | 933752-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 6-甲基咪唑并[1,2-a]吡啶-3-甲醛
• 中文别名: 6-甲基咪唑并[1,2-A]吡啶-3-甲醛
• 英文名称: 6-methylimidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 933752-89-7
• 化学式: C₉H₈N₂O
• mdl: MFCD09994344
• 分子量: 160.175
• InChiKey: DFECGQLPNSSUAQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  储存条件：2-8℃，请使用惰性气体保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Methylimidazo[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: 6-Methylimidazo[1,2-a]pyridine-3-carbaldehyde
CAS number: 933752-89-7

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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: C9H8N2O
Molecular weight: 160.2

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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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  6-甲基咪唑并[1,2-a]吡啶	6-methylimidazo[1,2-a]pyridine	874-38-4	C8H8N2	132.165

反应信息

• 作为反应物：
  描述：

  6-甲基咪唑并[1,2-a]吡啶-3-甲醛 在 盐酸 、 sodium tetrahydroborate 、 正丁基锂 、 nickel(II) chloride hexahydrate 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 16.75h， 生成 2-fluoro-3-(6-methylimidazo[1,2-a]pyridin-3-yl)-2-phosphonopropanoic acid
  参考文献：
  名称：

  鉴定膦酸酯的咪唑并[1,2- a ]吡啶环的优先位置，以开发Rab Geranylgeranyl Transferase（RGGT）抑制剂。

  摘要：

  Rab GTPase家族的成员是囊泡运输的主要监管者。当失调时，它们与许多病理状态相关。抑制RGGT（一种负责Rab GTPases的翻译后香叶基香叶基化反应的酶）代表了一种控制这些蛋白活性的方法。由于调节RGGT的分子数量有限，因此我们将分子建模与生物学分析相结合，以确定首次报道的RGGT抑制剂膦酰基羧酸酯的修饰方式如何合理地增进对它们的结构-活性关系的了解。我们已经确定了咪唑[1,2- a]吡啶环，可在不影响化合物效能的情况下对其进行修饰。如此修饰的化合物是Rab11A异戊烯基化的微摩尔抑制剂，同时对Rap1A / Rap1B修饰无活性，并具有抑制HeLa癌细胞系增殖的能力。这些发现通过分子对接得到合理化，分子对接认为膦酸和羧基的相互作用对于RGGT结合位点的膦酰基羧酸酯定位起决定性作用。

  DOI：

  10.1021/acs.jmedchem.7b00811
• 作为产物：
  描述：

  2-氨基-5-甲基吡啶 在 silver hexafluoroantimonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 生成 6-甲基咪唑并[1,2-a]吡啶-3-甲醛
  参考文献：
  名称：

  2-氨基吡啶和丙醛之间的多相金（I）催化环化生成 3-酰基咪唑并[1,2-a]吡啶

  摘要：

  在 3 mol% MCM-41 固定化膦金 (I) 配合物 (MCM-41-PPh3-AuCl) 和 AgSbF6 存在下，在 25 °C 的 CH2Cl2 中，在空气中实现 2-氨基吡啶和丙醛之间的异质环化，以良好的收率产生各种 3-酰基咪唑并[1,2-a]吡啶。这种非均相金 (I) 催化剂可以通过简单的程序轻松制备，通过反应溶液过滤回收并循环使用 7 次而不会显着降低活性。

  DOI：

  10.3184/174751918x15314807595487

文献信息

• Transition Metal-Mediated C═O and C═C Bond-Forming Reactions: A Regioselective Strategy for the Synthesis of Imidazo[1,2-<i>a</i>]pyridines and Imidazo[1,2-<i>a</i>]pyrazines
  作者：Hua Cao、Xiaohang Liu、Jinqiang Liao、Jianping Huang、Huifang Qiu、Qinlin Chen、Yaoyi Chen

  DOI：10.1021/jo501671x

  日期：2014.11.21

  A novel and convenient transformation for the regiospecific synthesis of functionalized imidazo[1,2-a]pyridine aldehydes/ketones and 3-vinyl imidazo[1,2-a]pyridines has been developed via copper(I)- and palladium(II)-catalyzed cyclization. The one-pot reaction proceeds smoothly with commercially available catalysts and affords the products in moderate to good yields. It represents an efficient approach

  一种新颖的和便利的转化为官能化的咪唑并特异合成[1,2一]吡啶醛/酮和3-乙烯基咪唑并[1,2一]吡啶已经经由铜开发（I） -和钯（II） -催化环化。一锅法反应使用市售催化剂可顺利进行，并以中等至良好的收率提供产物。它代表在温和条件下形成C–N，C═O和C═C键的有效方法。
• Cu-Catalyzed Synthesis of 3-Formyl Imidazo[1,2-<i>a</i>]pyridines and Imidazo[1,2-<i>a</i>]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources
  作者：Changqing Rao、Shaoyu Mai、Qiuling Song

  DOI：10.1021/acs.orglett.7b02015

  日期：2017.9.15

  A highly efficient synthesis of 3-formyl imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrimidine, under Cu-catalyzed aerobic oxidative conditions and by utilizing ethyl tertiary amines as carbon sources, is disclosed. A novel activation mode of ethyl tertiary amines in which simultaneous selective cleavage of C–C bond and C–N bond of ethyl group with molecular oxygen as terminal oxidant in this one-pot

  公开了在Cu催化的需氧氧化条件下并利用乙基叔胺作为碳源的3-甲酰基咪唑并[1,2- a ]吡啶和咪唑并[1,2- a ]嘧啶的高效合成方法。首次报道了一种乙基叔胺的新型活化方式，其中在此一锅操作方案中首次报道了用分子氧作为末端氧化剂同时选择性地裂解乙基的C–C键和C–N键。该反应具有广泛的底物范围，良好的官能团耐受性以及多样化且有价值的产品。
• Copper-Catalyzed Intramolecular Dehydrogenative Aminooxygenation: Direct Access to Formyl-Substituted Aromatic N-Heterocycles
  作者：Honggen Wang、Yong Wang、Dongdong Liang、Lanying Liu、Jiancun Zhang、Qiang Zhu

  DOI：10.1002/anie.201100362

  日期：2011.6.14

  A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper‐mediated oxygen activation process via a peroxy–copper(III)

  已经开发了通过分子内脱氢氨基氧化作用直接合成甲醛的方法。该方法在氧气下在DMF或DMA中使用催化量的铜（II），不需要其他氧化剂（请参见方案）。机理研究表明，醛的羰基氧原子是通过过氧铜（III）中间体通过铜介导的氧活化过程从氧衍生而来的。
• 一种合成甲酰基取代的咪唑并[1,2a]吡啶类化合物的方法
  申请人：浙江工业大学

  公开号：CN110577527A

  公开（公告）日：2019-12-17

  本发明公开了一种合成甲酰基取代的咪唑并[1，2a]吡啶类化合物的方法，按照如下步骤进行：以式Ⅰ所示取代吡啶烯丙基胺类化合物为起始物，在氧化剂作用下，以2,2,6,6‑四甲基哌啶氮氧化物为添加剂，以乙腈或乙腈与水的混合液为溶剂，于反应温度30℃～100℃下反应1～8小时，所得反应液经分离纯化制备得到式Ⅱ所示甲酰基取代的咪唑并[1，2a]吡啶类化合物。本发明安全环保，不产生废气废水；底物适应性好，各种取代基都可以实现芳构化/甲酰基化；反应条件温和；原料不需事先芳构化或甲酰基化，反应步骤简单，且是一种合成各种甲酰基取代的咪唑并[1，2a]吡啶类化合物的新路线。
• Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines
  作者：Damian Kusy、Waldemar Maniukiewicz、Katarzyna M. Błażewska

  DOI：10.1016/j.tetlet.2019.151244

  日期：2019.11

  An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2- a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.

  一种高效，无金属的3-甲酰基咪唑合成方法[1,2- 据报道有]吡啶。该方法利用可商购的基材，并且具有广泛的基材范围。分离了中间体烯胺，并提出了合理的反应机理。