1-甲苯磺酰基-1H-吡咯-3-羧酸甲酯 | 212071-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-甲苯磺酰基-1H-吡咯-3-羧酸甲酯
• 英文名称: methyl 1-tosyl-1H-pyrrole-3-carboxylate
• 英文别名: methyl 2-[1-(p-tolylsulfonyl)pyrrol-3-yl]acetate；methyl N-tosylpyrrole-3-carboxylate；methyl 1-(4-methylphenyl)sulfonylpyrrole-3-carboxylate
• CAS: 212071-00-6
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: DFOVPGKRRVEJGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 1-tosyl-1h-pyrrole-3-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-tosyl-1h-pyrrole-3-carboxylate
CAS number: 212071-00-6

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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: C13H13NO4S
Molecular weight: 279.3

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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, sulfur 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-甲苯磺酰基-1H-吡咯-3-羧酸甲酯 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以73.3%的产率得到1-(p-methylphenylsulfonyl)-3-pyrrolylmethanol
  参考文献：
  名称：

  CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO

  摘要：

  该发明涉及钙依赖性蛋白激酶1（CDPK1）的抑制剂及其药物制剂。该发明进一步涉及使用该发明的新型抑制剂治疗寄生虫感染的方法，例如弓形虫、疟原虫、人类小肠球虫或小肠球小弓形虫感染。

  公开号：

  US20210347780A1
• 作为产物：
  描述：

  2,3-丁二烯酸甲酯 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 生成 1-甲苯磺酰基-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines:  A Convenient Synthesis of Pentabromopseudilin

  摘要：

  The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron deficient imines is described. Triphenylphosphine-catalyzed reaction of-methyl a,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A:reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

  DOI：

  10.1021/jo9723063

文献信息

• Rh(II)-Catalyzed Monocyclopropanation of Pyrroles and Its Application to the Synthesis Pharmaceutically Relevant Compounds
  作者：Jiantao Fu、Nikolai Wurzer、Verena Lehner、Oliver Reiser、Huw M. L. Davies

  DOI：10.1021/acs.orglett.9b02250

  日期：2019.8.2

  we report Rh(II)-catalyzed monocyclopropanation reactions on pyrroles in the presence of aryldiazoacetates, providing the corresponding dearomatized products with high levels of enantioselectivity (up to >99% ee). Under the catalysis of Rh2(R-p-PhTPCP)4, a broad range of pyrrole substrates and aryldiazoacetates are shown to be compatible. Utilizing these valuable chiral building blocks, we further demonstrate

  在这里，我们报告在芳基重氮乙酸酯存在下，Rh（II）催化的吡咯在吡咯上的单环丙烷化反应，为相应的脱芳构产物提供了高水平的对映选择性（最高> 99％ee）。在Rh 2（R - p- PhTPCP）4的催化下，各种吡咯底物和芳基重氮乙酸酯显示出相容性。利用这些有价值的手性结构单元，我们通过从单环丙烷化产物合成均-β-脯氨酸类似物和β-氨基羧酸（β-ACC）衍生物，进一步证明了这种转化的应用。
• Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
  作者：Yao Ouyang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1002/anie.201803566

  日期：2018.6.4

  large number of reagents have been developed for the synthesis of trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is the use of less expensive and practical trifluoromethyl sources. We report herein the unprecedented direct trifluoromethylation of (hetero)arenes using trifluoromethanesulfonic anhydride as a radical trifluoromethylation reagent by merging photoredox

  已经开发了用于合成三氟甲基化化合物的大量试剂。然而，三氟甲基化反应中的持续挑战是使用较便宜且实用的三氟甲基来源。我们在此报道了通过合并光氧化还原催化作用和吡啶活化作用，使用三氟甲磺酸酐作为自由基三氟甲基化试剂，对（杂）芳烃进行了前所未有的直接三氟甲基化。此外，实现了将三氟甲磺酸酐的CF 3和OTf基团同时引入内部炔烃以进入四取代的三氟甲基化的烯烃。由于三氟甲磺酸酐是一种低成本且含量丰富的化学品，因此该方法为生产三氟甲基化化合物提供了一种经济高效的实用途径。
• CONDUCTING POLYMERS AND USES THEREOF
  申请人：Travas-Sejdic Jadranka

  公开号：US20090215958A1

  公开（公告）日：2009-08-27

  A conducting polymer including a conducting linker to connect a probe to the polymer, the linker including an unsaturated organic chain.

  一种导电聚合物，包括导电连接物将探针连接至聚合物，连接物包括不饱和有机链。
• Conducting polymers and uses thereof
  申请人：Travas-Sejdic Jadranka

  公开号：US08378058B2

  公开（公告）日：2013-02-19

  A conducting polymer including a conducting linker to connect a probe to the polymer, the linker including an unsaturated organic chain.

  一种导电聚合物，包括导电连接物将探针连接到聚合物上，连接物包括不饱和有机链。
• Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles
  作者：Zhenrong Xu、Xiyan Lu

  DOI：10.1016/s0040-4039(97)00656-4

  日期：1997.5

  In the presence of a catalytic amount of triphenylphosphine, methyl 2,3-butadienoate smoothly reacted with aromatic or heteroaromatic N-tosylimines at room temperature to afford the [3+2] cycloaddition product in excellent yield. (C) 1997 Elsevier Science Ltd.