1-甲基吡咯-2-羧酸甲酯 | 37619-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-甲基吡咯-2-羧酸甲酯
• 中文别名: N-甲基吡咯-2-甲酸甲酯；1-甲基-2-甲氧羧基吡咯甲酯；1-甲基吡咯-3-羧酸甲酯
• 英文名称: methyl N-methylpyrrole-2-carboxylate
• 英文别名: methyl 1-methyl-1H-pyrrole-2-carboxylate；Methyl 1-methylpyrrole-2-carboxylate
• CAS: 37619-24-2
• 化学式: C₇H₉NO₂
• mdl: MFCD00052747
• 分子量: 139.154
• InChiKey: APHVGKYWHWFAQV-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C (sublm)(Press: 0.2 Torr)
• 沸点：
  96-98°C 15mm
• 密度：
  1.07±0.1 g/cm3(Predicted)
• 闪点：
  96-98°C/15mm
• 稳定性/保质期：
  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 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：
  密封、阴凉、干燥保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 1-methylpyrrole-2-carboxylate
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: Methyl 1-methylpyrrole-2-carboxylate
CAS number: 37619-24-2

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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: C7H9NO2
Molecular weight: 139.2

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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：

  1-甲基吡咯-2-羧酸甲酯 在 乙醇 、 一水合肼 作用下， 生成 1-甲基-1H-吡咯-2-碳酰肼
  参考文献：
  名称：

  Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds^1,2

  摘要：

  DOI：

  10.1021/ja01104a046
• 作为产物：
  描述：

  吡咯-2-羧酸 在 4-二甲氨基吡啶 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.25h， 生成 1-甲基吡咯-2-羧酸甲酯
  参考文献：
  名称：

  通过路易斯酸介导的重排合成 Armeniaspirol A 的结构异构体 Pseudoarmeniaspirol A

  摘要：

  天然产物 armeniaspirol 在 α,β-二氯-α,β-不饱和内酰胺支架中具有独特的螺环 N,O-缩酮，已证明其合成具有挑战性。在此，我们描述了快速生成该支架的吡咯-2-羧酸衍生物的氧化氯化作用。这种氧化的范围扩展到一系列酯和酰胺。由于氧化裂解，吡咯-2-酮无法转化为内酰胺。该结果出乎意料，因为氯-亚美尼亚螺醇是通过吡咯-2-酮的氧化氯化合成的。对这种成功氧化的检查表明，由于邻近游离苯酚的分子内捕获，防止了碎片化，因此可以访问所需的支架。使用甲基N的产品-methyl pyrrole -2-carboxylate oxidation 7b，我们试图获得天然产物armeniaspirol 2；然而，意外的路易斯酸介导的重排导致了结构异构体 pseudoarmeniaspirol A 1的形成。合成了一小组拟亚美尼亚螺醇类似物，并评估了抗生素活性、对亚美尼亚螺醇、ClpXP 和 ClpYQ

  DOI：

  10.1021/acs.joc.2c02331

文献信息

• PYRROLE mTORC INHIBITORS AND USES THEREOF
  申请人：Navitor Pharmaceuticals, Inc.

  公开号：US20190389843A1

  公开（公告）日：2019-12-26

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• One-Pot Synthesis of Homoallylic Ketones from the Addition of Vinyl Grignard Reagent to Carboxylic Esters
  作者：Karl A. Hansford、James E. Dettwiler、William D. Lubell

  DOI：10.1021/ol0359822

  日期：2003.12.1

  Fifteen homoallylic ketones have been synthesized in 26-77% yields on treatment of aromatic, aliphatic, and alpha-amino methyl carboxylates with excess vinylmagnesium bromide and catalytic amounts of a copper salt in THF. Alpha-amino homoallylic ketones derived from N-protected alpha-amino esters possessing aliphatic and alcohol side chains were synthesized in > or =98% enantiomeric purity. [reaction:

  在用过量的乙烯基溴化镁和催化量的铜盐在THF中处理芳族，脂肪族和α-氨基甲基羧酸盐后，已以26-77％的产率合成了15个均烯丙基酮。衍生自具有脂肪族和醇侧链的N-保护的α-氨基酯衍生的α-氨基均烯丙基酮，其对映体纯度> 98％或= 98％。[反应：看文字]
• Direct C–H Arylation of Thiophenes at Low Catalyst Loading of a Phosphine-Free Bis(alkoxo)palladium Complex
  作者：Yabo Li、Jingran Wang、Mengmeng Huang、Zhiwei Wang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo402745b

  日期：2014.4.4

  An efficient phosphine-free direct C–H arylation of thiophenes at the α-position has been developed at low catalyst loading of bis(alkoxo)palladium complex (Cat.I, 0.1–0.2 mol %). The developed synthetic method can be applied to the synthesis of α-aryl/heteroaryl thiophenes from aryl or heteroaryl bromides in good to excellent yields and is compatible with the substrates bearing electron-donating or

  在双（烷氧基）钯配合物（Cat.I，0.1-0.2 mol％）的低催化剂负载下，已开发出一种有效的无磷的噻吩在α位上无膦直接CH芳基化的化合物。所开发的合成方法可用于从芳基或杂芳基溴化物以良好至优异的产率合成α-芳基/杂芳基噻吩，并且与带有给电子或吸电子基团的底物相容。噻吩2位和5位的反应性是相同的，并且在最佳条件下不依赖于空间位阻。该条件还可以以高转化率应用于其他杂环部分，例如苯并噻吩，苯并呋喃和吡咯。
• Cu-Mediated C–H ¹⁸F-Fluorination of Electron-Rich (Hetero)arenes
  作者：Matthew S. McCammant、Stephen Thompson、Allen F. Brooks、Shane W. Krska、Peter J. H. Scott、Melanie S. Sanford

  DOI：10.1021/acs.orglett.7b01902

  日期：2017.7.21

  to form a (mesityl)(aryl)iodonium salt. This salt is then used in situ in a Cu-mediated radiofluorination with [18F]KF. This approach leverages the stability and availability of electron-rich arene starting materials to enable mild late-stage radiofluorination of toluene, anisole, aniline, pyrrole, and thiophene derivatives. The radiofluorination has been automated to access a 41 mCi dose of an 18F-labeled

  该通讯描述了一种富电子芳烃的亲核放射性氟化方法。该反应涉及富电子芳烃与 MesI(OH)OT 的初始 C(sp 2 )–H 官能化，形成(异三叉基)(芳基)碘鎓盐。然后将该盐用于用[ 18 F]KF进行Cu介导的放射性氟化反应中。该方法利用富电子芳烃起始材料的稳定性和可用性，实现甲苯、苯甲醚、苯胺、吡咯和噻吩衍生物的温和后期放射性氟化。放射性氟化已自动获得 41 mCi 剂量的18 F 标记的尼美舒利衍生物，其比活性高 (2800 ± 700 Ci/mmol)。
• <i>Para</i>-Selective Cu-Catalyzed C–H Aryloxylation of Electron-Rich Arenes and Heteroarenes
  作者：Igors Sokolovs、Edgars Suna

  DOI：10.1021/acs.joc.5b02728

  日期：2016.1.15

  Cu-catalyzed reaction of phenols with electron-rich arene or heteroarene ligands of unsymmetrical diaryl-λ3-iodanes is a key step in the developed one-pot two-step method for intermolecular para-selective C–H aryloxylation of heteroarenes and arenes.

  铜-催化的与富电子芳烃或杂芳烃配体酚的反应不对称二芳基- λ 3 -iodanes是在分子间的发达一锅两步法的关键步骤对杂芳烃和芳烃-选择性C-H aryloxylation。

表征谱图