2-乙酰基-1-甲苯磺酰基吡咯 | 129666-99-5

• 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: 2-乙酰基-1-甲苯磺酰基吡咯
• 英文名称: 2-acetyl-1-(4-toluenesulfonyl)pyrrole
• 英文别名: 1-(p-tolylsulfonyl)-2-acetylpyrrole；2-acetyl-N-p-toluenesulfonylpyrrole；1-(1-tosyl-1H-pyrrol-2-yl)ethanone；2-acetyl-1-tosylpyrrole；1-[1-(4-methylphenyl)sulfonylpyrrol-2-yl]ethanone
• CAS: 129666-99-5
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD00436532
• 分子量: 263.317
• InChiKey: MYLYBCZMJRPTEU-UHFFFAOYSA-N

物化性质

• 沸点：
  442.1±47.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.5
• 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: 2-Acetyl-1-tosylpyrrole
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: 2-Acetyl-1-tosylpyrrole
CAS number: 129666-99-5

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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: C13H13NO3S
Molecular weight: 263.3

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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：

  2-乙酰基-1-甲苯磺酰基吡咯 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 26.0h， 以81%的产率得到2-乙基吡咯
  参考文献：
  名称：

  Modular Access to Complex Prodiginines: Total Synthesis of (+)-Roseophilin via its 2-Azafulvene Prototropisomer

  摘要：

  Ansa-bridged, prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.

  DOI：

  10.1021/ja400473v
• 作为产物：
  描述：

  1-(对甲苯磺酰基)吡咯 、 乙酸酐 在 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以80.5%的产率得到2-乙酰基-1-甲苯磺酰基吡咯
  参考文献：
  名称：

  主链上含吡咯单元的聚喹啉和聚噻唑啉的合成及性能

  摘要：

  合成并表征了一系列八种新的在主链上具有吡咯异构体单元的聚喹啉和聚蒽唑啉。新型聚合物显示出高玻璃化转变温度（T g = 242-339°C）和出色的热稳定性（空气中T 5％ = 398-536°C，TGA）。相比于系列polyanthrazolines的，该系列聚喹啉表现出更高的热稳定性，更好的溶解度在普通有机溶剂中，并降低最大吸收波长（λ一最大值）。与2,5-吡咯联动Polyanthrazolines显示异常高的λ一个最大值（565纳米）和小的带隙（2.02电子伏特）。溶液中的所有聚合物在10 -2之间的光致发光量子产率低％和10 -5％，激发态寿命为0.28-1.29 ns。探索了分子结构，特别是吡咯键结构，对电子结构，热力学以及聚合物某些光学性质的影响。建议使用聚合物主链中的氢键模型来解释异构体聚合物的性能差异。另外，选择了一种聚喹啉（PBM）来检查质子的电导率。结果表明，PBM / H

  DOI：

  10.1021/ma025768d

文献信息

• Pyrroles substituted by oligonucleotides
  申请人：Mandrand Bernard

  公开号：US20060189555A1

  公开（公告）日：2006-08-24

  The invention relates to novel pyrrole derivatives of the formula (I) which make it possible to immobilize and address oligonucleotides by electropolymerization. Said invention also relates to thus produced electroactive polymers and to methods for using them for detecting, identifying and dosing analytes in a sampe. (I) wherein R 1 is one type of oligonucleotide, Y is S or O, X is a spacer arm selected from —(CH 2 )—O—, —(CH 2 )PO—[(CH 2 ) 2 —O] q —, —(CH2 )r ; —CO—NR—(CH 2)r -0-, —CH 2r —NCH 3 —(CH 2 ) r —O—, —CH 2 ) r CO—NR′—[CH 2 ) 2 —O] s —, —(CH 2 ) r NCH 3 [(CH 2 ) 2 —O]S—, R′ is H or CH 3 , n is an integer number ranging from 1 to 5, p is an integer number ranging from 1 to 2, q is an integer number ranging from 1 to 4, r is an integer number ranging from 1 to 3, r′ is an integer number ranging from 1 to 3, s is an integer number ranging from 1 to 3, n, p, q, r, r′ and s are identical or different, a pyrrole cycle is substituted in a position 2, 3, 4 or 5.

  该发明涉及公式（I）的新型吡咯衍生物，可以通过电聚合固定和寻址寡核苷酸。该发明还涉及因此产生的电活性聚合物，以及使用它们用于检测、鉴定和定量样品中的分析物的方法。在公式（I）中，R1是一种类型的寡核苷酸，Y是S或O，X是从—（CH2）—O—、—（CH2）PO—（（CH2）2—O）q—、—（CH2）r；—CO—NR—（CH2r）-O-、—CH2r—NCH3—（CH2）r—O—、—CH2rCO—NR′—（CH2）2—O）s—、—（CH2）rNCH3（（CH2）2—O）S—中选择的间隔臂，R′是H或CH3，n是从1到5的整数，p是从1到2的整数，q是从1到4的整数，r是从1到3的整数，r′是从1到3的整数，s是从1到3的整数，n、p、q、r、r′和s是相同或不同的，吡咯环在位置2、3、4或5上被取代。
• Synthesis of Azaheterocycles from Aryl Ketone <i>O</i>-Acetyl Oximes and Internal Alkynes by Cu–Rh Bimetallic Relay Catalysts
  作者：Pei Chui Too、Sze Hui Chua、Siong Heng Wong、Shunsuke Chiba

  DOI：10.1021/jo200897q

  日期：2011.8.5

  A synthetic method for azaheterocycles from aryl ketone O-acetyl oximes and internal alkynes has been developed by using the Cu(OAc)2–[Cp*RhCl2]2 bimetallic catalytic system. The reactions proceeded with both of anti- and syn-isomers of oximes with a wide scope of substituents. The Cu–Rh bimetallic system could be applied for the synthesis of isoquinolines as well as β-carboline, furo[2.3-c]pyridine

  利用Cu（OAc）2- [Cp * RhCl 2 ] 2双金属催化体系，开发了一种由芳基酮O-乙酰基肟和内部炔烃合成氮杂杂环的方法。该反应在具有广泛取代基的肟的反-和顺-异构体上进行。Cu-Rh双金属系统可用于合成异喹啉以及β-咔啉，呋喃[2.3- c ]吡啶，吡咯并[2,3- c ]吡啶和噻吩并[2,3- c ]吡啶衍生物。
• Cobalt-Catalyzed Oxygenation/Dearomatization of Furans
  作者：Jonathan P. Oswald、K. A. Woerpel

  DOI：10.1021/acs.joc.8b01183

  日期：2018.8.17

  The dearomatization of aromatic compounds using cobalt(II) acetylacetonate with triplet oxygen and triethylsilane converts furans, benzofurans, pyrroles, and thiophenes to a variety of products, including lactones, silyl peroxides, and ketones.

  使用乙酰丙酮钴（II）与三重态氧和三乙基硅烷对芳香族化合物进行脱芳香化处理，可将呋喃，苯并呋喃，吡咯和噻吩转化为多种产品，包括内酯，过氧化甲硅烷基和酮。
• Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles
  作者：Joydev K. Laha、Shubhra Sharma、Rohan A. Bhimpuria、Neetu Dayal、Gurudutt Dubey、Prasad V. Bharatam

  DOI：10.1039/c7nj01709j

  日期：——

  oxidative C-2 arylation followed by sulfonyl migration is described. The simple, easy access to the highly functionalized free-NH pyrroles secures opportunities for the preparation of compounds with promising biological activities in contemporary organic synthesis. The event of sulfonyl migration from pyrrole-N to C-3 is thermodynamically favored as revealed by density functional methods. The different plausible

  描述了通过钯催化的氧化C-2芳基化然后由磺酰基迁移而首次开发的由N-磺酰基吡咯一次合成2-芳基-3-烷基/芳基-磺酰基-（NH）-吡咯的方法。简单，容易地获得高度官能化的游离NH吡咯，为制备具有当代有机合成中具有良好生物活性的化合物提供了机会。如密度泛函方法所揭示，磺酰基从吡咯-N迁移至C-3的事件在热力学上是有利的。还讨论了磺酰基迁移的不同可能机理。
• A new method for the acylation of pyrroles
  作者：Chuanjun Song、David W. Knight、Maria A. Whatton (neé Fagan)

  DOI：10.1016/j.tetlet.2004.10.133

  日期：2004.12

  N-Tosylpyrroles can be very efficiently converted into the corresponding 2-acylpyrroles by reaction with carboxylic acids and trifluoroacetic anhydride; little or none of the isomeric 3-acyl derivatives are formed.

  Ñ -Tosylpyrroles可以非常有效地转换成与羧酸和三氟乙酸酐反应相应的2- acylpyrroles; 几乎没有或没有形成任何异构的3-酰基衍生物。