3-乙酰基-1-甲苯磺酰基吡咯 | 106058-85-9

• 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: 3-乙酰基-1-甲苯磺酰基吡咯
• 英文名称: 1-(1-tosyl-1H-pyrrol-3-yl)ethan-1-one
• 英文别名: 3-acetyl-1-tosylpyrrole；N-tosyl-3-acetyl pyrrole；1-(1-Tosyl-1h-pyrrol-3-yl)ethanone；1-[1-(4-methylphenyl)sulfonylpyrrol-3-yl]ethanone
• CAS: 106058-85-9
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD00143087
• 分子量: 263.317
• InChiKey: NDOSNRLQNYYVKV-UHFFFAOYSA-N

物化性质

• 熔点：
  68-72°C
• 沸点：
  88 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 安全说明：
  S26
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  存储条件：2-8°C，干燥密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-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: 3-Acetyl-1-tosylpyrrole
CAS number: 106058-85-9

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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：

  3-乙酰基-1-甲苯磺酰基吡咯 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 3-乙基-1H-吡咯
  参考文献：
  名称：

  具有近定量双向光开关的吡咯半硫靛抗有丝分裂剂，可以单细胞精度光控制细胞微管动力学**

  摘要：

  我们通过合理设计细胞骨架蛋白微管蛋白的光药物PHTub抑制剂，报告了新兴的近定量光开关吡咯半硫靛蓝的首次细胞应用。PHTub允许在活细胞中同时进行可见光成像和光开关，提供微管动力学的细胞精确光调制，以及对细胞周期进程和细胞死亡的光控制。这是首次将半硫靛蓝光药物用于活细胞的高时空分辨率生物控制。它还通过启用暗活性设计来克服细胞光图案化过程中残留的背景活性，展示了近定量光开关的实用性。这项工作为使用PHTub进行高精度微管研究开辟了新视野，并展示了吡咯半硫靛蓝作为一系列其他生物靶标的光控制的有价值支架的细胞适用性。

  DOI：

  10.1002/anie.202104794
• 作为产物：
  描述：

  吡咯-3-甲醛 在 4-二甲氨基吡啶 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 3-乙酰基-1-甲苯磺酰基吡咯
  参考文献：
  名称：

  Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

  摘要：

  A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

  DOI：

  10.1021/jacs.5b00613

文献信息

• [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION<br/>[FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)
  申请人：ASTEX THERAPEUTICS LTD

  公开号：WO2013064538A1

  公开（公告）日：2013-05-10

  The invention provides compounds of the formula (I): or a salt, N-oxide or tautomer thereof, wherein A is CH, CF or nitrogen; E is CH, CF or nitrogen; and R0 is hydrogen or C1-2 alkyl; R1a is selected from CONH2; CO2H; an optionally substituted acyclic C1-8 hydrocarbon group; and an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1, 2, 3 or 4 are heteroatom ring members selected from O, N and S; R2 is selected from hydrogen and a group R2a; R2a is selected from an optionally substituted acyclic d-8 hydrocarbon group; an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1 or 2 ring members are heteroatom ring members selected from O, N and S; and an optionally substituted bicyclic heterocyclic group of 9 or 10 ring members, of which 1 or 2 ring members are nitrogen atoms; wherein at least one of R1 and R2 is other than hydrogen; R3 is an optionally substituted 3- to 10-membered monocyclic or bicyclic carbocyclic or heterocyclic ring containing 0, 1, 2 or 3 heteroatom ring members selected from N, O and S; R4a is selected from halogen; cyano; C1-4 alkyl optionally substituted with one or more fluorine atoms; C1-4 alkoxy optionally substituted with one or more fluorine atoms; hydroxy-C1-4 alkyl; and C1-2 alkoxy-C1-4 alkyl; R5 is selected from hydrogen and a substituent R5a; and R5a is selected from C1-2 alkyl optionally substituted with one or more fluorine atoms; C1-3 alkoxy optionally substituted with one or more fluorine atoms; halogen; cyclopropyl; cyano; and amino, The compounds have activity against hepatitis C virus and can be used in the prevention or treatment of hepatitis C viral infections.

  该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。
• 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 (±)-γ-Lycorane by Using an Intramolecular Friedel–Crafts Reaction
  作者：Bao Doan、Xin Tan、Chin Ang、Roderick Bates

  DOI：10.1055/s-0036-1589067

  日期：2017.10

  Abstract A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block. The synthesis employs both an intermolecular and an intramolecular Friedel–Crafts reaction, as well as a completely diastereoselective hydrogenation of a late-stage pyrrole intermediate. A total synthesis of γ-lycorane has been achieved by employing N-tosylpyrrole as a key building block

  摘要 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。 通过使用N-甲苯磺酰基吡咯作为主要的结构单元，可以实现γ-二十烷的全合成。合成过程同时使用分子间和分子内Friedel-Crafts反应，以及后期吡咯中间体的完全非对映选择性氢化。
• Direct Enamido C(sp²)−H Diphosphorylation Enabled by a PCET‐Triggered Double Radical Relay: Access to<i>gem</i>‐Bisphosphonates
  作者：Hao‐Qiang Cao、Hao‐Nan Liu、Zhe‐Yuan Liu、Bao‐Kun Qiao、Fa‐Guang Zhang、Jun‐An Ma

  DOI：10.1002/chem.202000517

  日期：2020.4.24

  electron-transfer (PCET)-triggered enamido C(sp2 )-H diphosphorylation. This reaction represents a rare example of realizing the challenging double C-P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves

  在这里，我们报告通过质子耦合电子转移（PCET）触发的烯键式C（sp2）-H双磷酸化来构造有价值的gem-BP的新颖而直接的协议。该反应代表了一个难得的例子，该例子实现了在单个碳原子上形成具有挑战性的双CP键，从而在银介导的条件下轻松地从简单的酰胺中获得了多种结构多样的双膦酸酯。初步的机理研究表明，二磷酸化涉及两轮PCET引发的自由基中继过程。
• Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents
  作者：Raphael K. Klake、Samantha L. Gargaro、Skyler L. Gentry、Sharon O. Elele、Joshua D. Sieber

  DOI：10.1021/acs.orglett.9b02973

  日期：2019.10.4

  N-substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocontrol. This methodology allows access to chiral γ-hydroxyaldehyde equivalents that were applied in the synthesis of chiral γ-lactones and 2,5-disubstitued tetrahydrofurans.

  我们报道了利用手性烯丙酰胺产生的N-取代的烯丙基等价物对酮进行烯丙基化的立体选择性方法的发展。通过为Cu催化剂选择合适的配体，可以获得良好的非对映异构控制的高线性选择性。该方法允许获得手性γ-羟醛等效物，该手性γ-羟醛等效物用于合成手性γ-内酯和2,5-二取代的四氢呋喃。