1-甲磺酰基-2,5-二氢吡咯 | 246540-50-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 1-甲磺酰基-2,5-二氢吡咯
• 英文名称: 1-methanesulfonyl-2,5-dihydropyrrole
• 英文别名: 1-(methylsulfonyl)-2,5-dihydro-1H-pyrrole；1-methylsulfonyl-2,5-dihydropyrrole
• CAS: 246540-50-1
• 化学式: C₅H₉NO₂S
• 分子量: 147.198
• InChiKey: MYAFMESORGRBTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  239.5±43.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

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: 1-Methanesulfonyl-2,5-dihydropyrrole
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: 1-Methanesulfonyl-2,5-dihydropyrrole
CAS number: 246540-50-1

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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, refrigerated.
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: C5H9NO2S
Molecular weight: 147.2

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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, 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-甲磺酰基-2,5-二氢吡咯 在 盐酸 、 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 3-Chloro-1-methylsulfonylpyrrolidine
  参考文献：
  名称：

  一种3-氨基吡咯烷盐酸盐的合成方法

  摘要：

  本发明公开了一种3‑氨基吡咯烷盐酸盐的合成方法，包括S1：化合物I与化合物II环合反应得化合物III；S2：化合物III在卤化氢气体作用下得化合物IV；S3：用化合物IV与有机磺酰胺在碱存在下反应得化合物V；S4：化合物V与酸反应得到化合物VI。该3‑氨基吡咯烷盐酸盐的合成方法引进芳、烷磺酸基对两个氨基进行保护，脱保护时，可以使用单一反应条件，有效减少操作步骤；用苄基保护氨时，脱保护要用到贵金属钯和高压催化加氢，生产成本高，操作风险性高，使用芳、烷磺酸基保护，脱保护只需用酸催化水解，反应条件温和。

  公开号：

  CN112574086B
• 作为产物：
  描述：

  1-methylsulfonylpyrrole 在 sodium cyanoborohydride 作用下， 以 三氟乙酸 为溶剂， 以80%的产率得到1-甲磺酰基-2,5-二氢吡咯
  参考文献：
  名称：

  Chemoselective reduction of 2-acyl-N-sulfonylpyrroles: Synthesis of 3-pyrrolines and 2-alkylpyrroles

  摘要：

  吡咯的部分还原并不是一种常见的实践，尽管它提供了一条潜在的途径来合成常用于合成的吡咯啉构建块。我们研究了2-酰基-N-磺酰吡咯的还原，通过改变氢化剂来源和溶剂，实现了化学选择性还原，得到高产率的3-吡咯啉和烷基吡咯。

  DOI：

  10.1039/c1ob05111c

文献信息

• Direct Synthesis of Previously Inaccessible Bridgehead Azabicyclics by Intramolecular Cyclization of α-Sulfonamido and α-Sulfonimido Radicals
  作者：Leo A. Paquette、Choon Sup Ra、Jeffrey D. Schloss、Silvana M. Leit、Judith C. Gallucci

  DOI：10.1021/jo010216z

  日期：2001.5.1

  Syntheses of the first bridgehead sultams and the only known bridgehead disulfonimide are described. Both approaches capitalize on the electrophilicity of alpha-sulfonyl radicals and their propensity to undergo intramolecular ring closure. Where double bonds are concerned, 5-exo and 6-exo pathways operate preferentially as long as structural strain is not excessive. When the reaction center is a carbon-carbon

  描述了第一个桥头磺胺和唯一已知的桥头二磺酰亚胺的合成。两种方法都利用了α-磺酰基的亲电性和它们进行分子内闭环的倾向。在涉及双键的情况下，只要结构应变不过度，5-exo和6-exo途径就优先起作用。当反应中心是碳-碳三键时，第一个环化反应会产生乙烯基，该乙烯基具有足够的反应活性以捕获溶剂苯。在45的情况下，该顺序反应重要地导致引入足够活化的苯乙烯官能团以允许第二个闭环在动力学上可行。通过X射线晶体学方法已经阐明了12和17的固态结构特征。尽管与氮孤对相对于相邻磺酰基的排列方式的规范存在重大差异，但这些化合物仍具有良好的水解稳定性。对于13，可能产生α-磺酰胺碳负离子，并且已经实现了用乙酸铬酰的区域特异性氧化。
• An Unprecedented Stereoselective Titanium-Mediated Dihydrodimerization of Allyl Ethers and Allylamines
  作者：Armin de Meijere、Björn Stecker、Alexandre Kourdioukov、Craig M. Williams

  DOI：10.1055/s-2000-6297

  日期：——

  3-Phenylallyl ether 17, 2,5-dihydrofuran (1) and N-acceptor-substituted 2,5-dihydropyrrols 4, 6, 8, 10, 12 upon treatment with cyclohexylmagnesium bromide in the presence of Ti(Oi-Pr)4 were found to undergo a diastereoselective dihydrodimerization affording 1,5-dienes, d,l-2,3-diethenylbutane-1,4-diol (51% yield) and d,l-2,3-diethenyl-1,4-bis(sulfonylamino)butanes (43 - 52%), respectively. In the presence of titanium bis(4R,5R)-taddolate, the dihydrodimerization of 1 proceeded with 35 - 38% chemical yield and up to 94% ee.

  在 Ti(Oi-Pr)4存在下，用环己基溴化镁处理 3-苯基烯丙基醚 17、2,5-二氢呋喃（1）和 N-受体取代的 2,5-二氢吡咯 4、6、8、10、12 后，发现它们会发生非对映选择性二氢二聚化，生成 1、5-二烯、d,l-2,3-二乙烯基-1,4-丁二醇（产率 51%）和 d,l-2,3-二乙烯基-1,4-双（磺酰氨基）丁烷（产率 43 - 52%）。在双(4R,5R)-涕灭酸钛存在下，1 的二氢化二聚反应以 35 - 38% 的化学收率进行，ee 值高达 94%。
• SUBSTITUTED 2-AMINO-FUSED HETEROCYCLIC COMPOUNDS
  申请人：Huang Liming

  公开号：US20100056506A1

  公开（公告）日：2010-03-04

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, wherein: R 1 , R 2 , Z 1 , t, and ring A are as defined in the specification. The invention also relates to pharmaceutical compositions comprising the compounds of formula (I) and methods of treating a condition that is mediated by the modulation of JNK, such as diabetes, the method comprising administering to a mammal an effective amount of a compound of formula (I).

  本发明涉及公式（I）的化合物，或其药学上可接受的盐或溶剂，其中：R1、R2、Z1、t和环A如规范中所定义。本发明还涉及包含公式（I）化合物的制药组合物以及治疗通过调节JNK介导的疾病的方法，如糖尿病，该方法包括向哺乳动物投与公式（I）化合物的有效量。
• Substituted 2-amino-fused heterocyclic compounds
  申请人：Pfizer Inc.

  公开号：US07998978B2

  公开（公告）日：2011-08-16

  The present invention relates to compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof, wherein: R1, R2, Z1, t, and ring A are as defined in the specification. The invention also relates to pharmaceutical compositions comprising the compounds of formula (I) and methods of treating a condition that is mediated by the modulation of JNK, such as diabetes, the method comprising administering to a mammal an effective amount of a compound of formula (I).

  本发明涉及式（I）的化合物，或其药学上可接受的盐或溶剂，其中：R1、R2、Z1、t和环A如规范中所定义。本发明还涉及包括式（I）的化合物的制药组合物以及用于治疗通过调节JNK介导的疾病，如糖尿病的方法，该方法包括向哺乳动物投与式（I）的化合物的有效量。
• Synthesis and Protein Kinase C Inhibitory Activities of Balanol Analogs with Replacement of the Perhydroazepine Moiety
  作者：Yen-Shi Lai、José S. Mendoza、G. Erik Jagdmann、David S. Menaldino、Christopher K. Biggers、Julia M. Heerding、Joseph W. Wilson、Steven E. Hall、Jack B. Jiang、William P. Janzen、Lawrence M. Ballas

  DOI：10.1021/jm960497g

  日期：1997.1.1

  Balanol is a potent protein kinase C (PKC) inhibitor that is structurally composed of a benzophenone diacid, a 4-hydroxybenzamide, and a perhydroazepine ring. A number of balanol analogs in which the perhydroazepine moiety is replaced have been synthesized and their biological activities evaluated against both PKC and cAMP-dependent kinase (PKA). The results suggested that the activity and the isozyme/kinase selectivity of these compounds are largely related to the conformation about this nonaromatic structural element of the molecules.