吡咯-3-甲醛 | 7126-39-8

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 吡咯-3-甲醛
• 中文别名: 3-吡咯甲醛
• 英文名称: pyrrole-3-carboxaldehyde
• 英文别名: 1H-pyrrole-3-carbaldehyde；pyrrole-3-carbaldehyde；3-formylpyrrole；1H-pyrrole-3-carboxaldehyde；pyrrole-3-carboxyaldehyde；1H pyrrole-3-formaldehyde
• CAS: 7126-39-8
• 化学式: C₅H₅NO
• mdl: MFCD03426733
• 分子量: 95.1008
• InChiKey: CHNYVNOFAWYUEG-UHFFFAOYSA-N

物化性质

• 熔点：
  65-68℃
• 沸点：
  238.3±13.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 溶解度：
  易溶于可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S36/37
• 危险类别码：
  R43
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于惰性气体中，避免与空气接触。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
1H-Pyrrole-3-carbaldehyde
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
1H-Pyrrole-3-carbaldehyde
Ingredient name:
CAS number: 7126-39-8

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5NO
Molecular weight: 95.1

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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.

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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

制备方法与用途

吡咯-3-甲醛是一种生物化学试剂，可用作生物材料或有机化合物，广泛应用于生命科学领域的研究。

反应信息

• 作为反应物：
  描述：

  吡咯-3-甲醛 在 一水合肼 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 以73%的产率得到3-甲基吡咯
  参考文献：
  名称：

  氨基酸型念珠菌百合生物碱和百合碱的合成；NMR光谱和DFT构象分析的协同使用确定它们的相对构型

  摘要：

  我们据此报道了从假丝百合中分离出的六个外消旋生物碱的合成。它们的共同结构特征是五元内酰胺环，在黄酮类生物碱lalaline的情况下，其附着在分子的芳香核上，而在其他五种化合物则通过氨基功能连接到吡咯烷酮环的氮原子上。这些天然产物的合成是通过曼尼希型烷基化反应，以环状N-酰基亚胺离子为中间体。除了合成以外，这些天然产物迄今尚未探索的立体化学是通过基于NMR的质子-质子距离测量和在DFT级进行的理论构象分析相结合来确定的。

  DOI：

  10.1016/j.tet.2020.131827
• 作为产物：
  描述：

  (氯亚甲基)二甲基氯化铵 在 sodium hydride 、 三异丙基氯硅烷 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以38%的产率得到吡咯-3-甲醛
  参考文献：
  名称：

  Acid secretion inhibitor

  摘要：

  本发明提供一种具有优越的抑制酸分泌作用并显示抗溃疡活性等的化合物。本发明提供一种由式(I)表示的化合物，其中R1是一种含氮的单环杂环基，可选择地与苯环或杂环缩合，该含氮的单环杂环基可选择地与苯环或杂环缩合，可选择地具有取代基，R2是可选择地取代的C6-14芳基，可选择地取代的噻吩基或可选择地取代的吡啶基，R3和R4分别是氢原子，或者R3和R4中的一个是氢原子，另一个是可选择地取代的较低烷基基团、酰基、卤原子、氰基或硝基，R5是烷基或其盐。

  公开号：

  US20070060623A1

文献信息

• Addition reaction of various azoles to perfluoromethyl vinyl ether
  作者：Kirill I. Petko、Andrey A. Filatov

  DOI：10.1007/s10593-021-02965-9

  日期：2021.6

  The addition reaction of perfluoromethyl vinyl ether to various azoles – derivatives of pyrrole, imidazole, pyrazole, indole, benzotriazole, carbazole, and triazole has been demonstrated. The reaction conditions depended both on melting point and nucleophilicity of the heterocycle. The obtained products are hydrolytically and thermally stable, have highly lipophilic moiety and can serve as useful precursors

  已证明全氟甲基乙烯基醚与各种唑类（吡咯、咪唑、吡唑、吲哚、苯并三唑、咔唑和三唑的衍生物）的加成反应。反应条件取决于杂环的熔点和亲核性。所得产物具有水解和热稳定性，具有高度亲脂性，可作为不同生物活性化合物合成的有用前体。
• Platinum-Catalyzed Domino Reaction with Benziodoxole Reagents for Accessing Benzene-Alkynylated Indoles
  作者：Yifan Li、Jerome Waser

  DOI：10.1002/anie.201412321

  日期：2015.4.27

  platinum‐catalyzed cyclization/alkynylation domino process to selectively obtain C5‐ or C6‐functionalized indoles starting from easily available pyrroles. The work combines, for the first time, a platinum catalyst with ethynylbenziodoxole hypervalent iodine reagents in a domino process for the synthesis of polyfunctionalized arene rings and gives access to important building blocks for the synthesis of bioactive

  吲哚在天然产物，生物活性分子和有机材料中无处不在。因此，它们的合成或功能化是有机化学研究的重要领域。大多数工作着重于吡咯环的安装或改装。使用未取代的吡咯环访问苯环官能化的吲哚仍然更具挑战性。本文报道的是铂催化的环化/炔基多米诺骨牌工艺，从易于获得的吡咯开始，选择性地获得C5或C6功能化的吲哚。该工作首次在多米诺骨牌工艺中将铂催化剂与乙炔基苯并恶唑高价碘试剂结合在一起，以合成多官能化的芳烃环，并为生物活性化合物和有机材料的合成提供了重要的组成部分。
• Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones
  作者：Amy Boylan、Thien S. Nguyen、Brian J. Lundy、Jian-Yuan Li、Ravikrishna Vallakati、Sasha Sundstrom、Jeremy A. May

  DOI：10.3390/molecules26061615

  日期：——

  Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the

  影响烯基硼酸与杂芳基连接的烯酮共轭加成反应速率的两个关键因素：感应吸电子杂原子与成键位点的接近度以及可用杂原子孤对对稳定产生的正电荷的共振贡献在烯酮β-位。对于前者，杂原子距离烯酮β-碳越近，反应越快。对于后者，苄基阳离子电荷的共振稳定性更强，可加速反应。因此，反应速率通过感应吸电子元件的更接近而增加，但如果涉及共振效应，则观察到具有给电子能力的速率增加。提出了异构底物这些趋势的证据，并且这些见解的应用允许反应条件改善与以前有问题的底物的反应性。
• [EN] SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY<br/>[FR] DÉRIVÉS D'OXINDOLE SPIRO-SUBSTITUÉS AYANT UNE ACTIVITÉ SUR AMPK
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014202580A1

  公开（公告）日：2014-12-24

  The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

  本发明涉及具有有价值的药理特性的式(I)化合物，特别是AMPK激活剂，因此在治疗某些可以通过激活该受体预防或治疗的疾病方面具有用处。这些化合物适用于治疗和预防可以受该受体影响的疾病，如代谢性疾病，特别是2型糖尿病。
• Direct aldol and tandem Mannich reactions in room temperature ammonia solutions
  作者：Lichun Feng、Lijin Xu、Kimhung Lam、Zhongyuan Zhou、C.W. Yip、Albert S.C. Chan

  DOI：10.1016/j.tetlet.2005.10.050

  日期：2005.12

  An economical, simple, and efficient direct aldol reaction via the double activation of both aldehydes and ketones by ammonia has been developed. An unprecedented tandem Mannich reaction was observed when hydroxybenzaldehydes, pyrrole-2-carboxyaldehyde, and indole-3-carboxyaldehyde were employed to afford 2,2-dimethyl-6-aryl-4-pyrilidinones in moderate to good yields.

  已经开发了通过氨对醛和酮的双重活化而进行的经济，简单和有效的直接羟醛反应。当使用羟基苯甲醛，吡咯-2-羧基醛和吲哚-3-羧基醛以中等到良好的收率得到2,2-二甲基-6-芳基-4-吡咯烷酮时，观察到了前所未有的串联曼尼希反应。

表征谱图