2-(2-噻吩基)吡咯烷 | 90090-64-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(2-噻吩基)吡咯烷
• 中文别名: 2-(噻吩-2)-吡咯烷；2-(噻吩-2-基)吡咯烷
• 英文名称: 2-(thiophen-2-yl)pyrrolidine
• 英文别名: 2-thiophen-2-ylpyrrolidine
• CAS: 90090-64-5
• 化学式: C₈H₁₁NS
• mdl: MFCD00052889
• 分子量: 153.248
• InChiKey: BNUVOMNEUJWHCF-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO（微溶）、乙醇（微溶）、甲醇（微溶）
• 稳定性/保质期：

  按规定使用和贮存的不会分解，避氧化物、潮湿。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi,C
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  存放在密闭、阴凉、干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-(Thiophen-2-yl)pyrrolidine
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-(Thiophen-2-yl)pyrrolidine
Ingredient name:
CAS number: 90090-64-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H11NS
Molecular weight: 153.2

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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：

  2-(2-噻吩基)吡咯烷 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 (1R,2R)-1-Methyl-2-thiophen-2-yl-1-trimethylsilanylmethyl-pyrrolidinium; iodide
  参考文献：
  名称：

  Rearrangement of cis- and trans-1-methyl-2-(2-thienyl)pyrrolidinium 1-methylides in a non-basic medium

  摘要：

  在非碱性介质中生成的顺式-1-甲基-2-(2-噻吩基)吡咯烷鎓 1-甲酰胺顺式-2 异构化为(E)-和(Z)-5-甲基-3a,4,5,6,7,8-六氢噻吩并[3,2-c]偶氮嗪的混合物，即(E)-6 和(Z)-6。后者 (Z)-6 在水中环化为顺式-类-顺式-5-甲基-3a,6,7,8,8a,8b-六氢-4H-噻吩并[2′,3′-c]吡咯并[1,2-a]吡咯鎓盐 8；反式-2 通过自由基裂解和再结合途径得到 1-甲基-3-（2-噻吩基）哌啶 7 和 (E)-6 的混合物。

  DOI：

  10.1039/a703068a
• 作为产物：
  描述：

  4-di(2-thienyl)-1,4-butanedione 在 3 A molecular sieve 、 甲酸铵 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以32%的产率得到2-(2-噻吩基)吡咯烷
  参考文献：
  名称：

  A Convenient Method for C-Azanucleosides Synthesis

  摘要：

  DOI：

  10.1021/jo960523i
• 作为试剂：
  描述：

  2,4-二硝基酚 在 3-氟-5-(三氟甲基)苯乙酮 、 2-(2-噻吩基)吡咯烷 、 sodium carbonate 作用下， 反应 3.5h， 以82%的产率得到2-氨基-4-硝基苯酚
  参考文献：
  名称：

  一种醋丁洛尔药物中间体2-氨基-4-硝基苯酚的合成方法

  摘要：

  本发明公开了一种醋丁洛尔药物中间体2?氨基?4?硝基苯酚的合成方法,通过将2，4?二硝基苯酚加入3?氟?5?(三氟甲基)苯乙酮和碳酸钠溶液混合溶液中，升高温度，滴加2?(噻吩?2?基)吡咯烷,加完后继续搅拌，再经过过滤、降温析出固体，将固体溶于二甲亚砜溶液中，加入草酸溶液，再经过分子筛脱色、抽滤、洗涤、重结晶，得晶体2?氨基?4?硝基苯酚。相比于传统的合成方法，本发明提供的合成方法，反应收率大大提高，同时本发明提供了一种新的合成路线，为进一步提升反应收率打下了良好的基础。

  公开号：

  CN105777560A

文献信息

• Palladium-catalyzed ortho-olefination of 2-arylpyrrolidines: A tool for increasing structural complexity in nitrogen heterocycles
  作者：Pablo D. Legarda、Alfonso García-Rubia、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1016/j.tet.2018.05.076

  日期：2018.7

  of the (2-pyridyl)sulfonyl unit as directing functionality and readily removable N-protecting group has enabled an efficient and practical transformation of 2-arylpyrrolidine derivatives into more complex tricyclic frameworks via palladium-catalyzed ortho-olefination with electron deficient alkenes and subsequent cyclization upon N-deprotection under mild conditions. The key cross coupling step in the

  （2-吡啶基）磺酰基单元作为直接官能团和易于除去的N-保护基团的双重作用使得能够通过钯催化的与缺电子烯烃的邻位烯烃化反应将2-芳基吡咯烷衍生物有效而实用地转化为更复杂的三环骨架。和随后在温和条件下在N-脱保护下环化。在三氟甲磺酸N-氟-2,4,6-三甲基吡啶鎓（[F +]）的存在下，关键的交叉偶联步骤既高效又可耐受两个偶联伙伴处的各种空间和电子变化。通过的还原条件适当选择，Ñ-磺酰基脱保护基可以选择性地形成苯并-稠合的吡咯烷或稠合的吡咯烷基-苯并氮杂framework骨架。
• CHEMICAL COMPOUNDS
  申请人：Deng Jianghe

  公开号：US20090143372A1

  公开（公告）日：2009-06-04

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  这项发明涉及新型吲哚羧酰胺衍生物。具体而言，该发明涉及符合以下式I的化合物： 其中R1、R2、R3、U和V如下定义，并且其药学上可接受的盐。该发明的化合物是IKK2的抑制剂，可用于治疗与不当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和慢性阻塞性肺病（COPD）。因此，该发明进一步涉及包含该发明化合物的药物组合物。该发明还进一步涉及使用该发明化合物或包含该发明化合物的药物组合物抑制IKK2活性和治疗相关疾病的方法。
• [EN] 5-AMINO-8-(4-PYRIDYL)-[1,2,4]TRIAZOLO[4,3-C]PYRIMIDIN-3-ONE COMPOUNDS FOR USE AGAINST CANCER<br/>[FR] COMPOSÉS DE 5-AMINO-8-(4-PYRIDYL)-[1,2,4]TRIAZOLO [4,3-C]PYRIMIDIN-3-ONE DESTINÉS À ÊTRE UTILISÉS CONTRE LE CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2021191378A1

  公开（公告）日：2021-09-30

  Described herein are triazalone compounds of Formula (I) and pharmaceutically acceptable salts thereof. Methods of making and using compounds of Formula (I) are also described. Compounds of Formula (I) and pharmaceutically acceptable salts thereof can be useful as adenosine receptor antagonists, for example in the treatment of diseases or conditions mediated by the adenosine receptor, such as cancer, movement disorders, or attention disorders.

  本文描述了式（I）的三唑酮化合物及其药用盐。还描述了制备和使用式（I）化合物的方法。式（I）的化合物及其药用盐可用作腺苷受体拮抗剂，例如在治疗由腺苷受体介导的疾病或症状，如癌症、运动障碍或注意力障碍方面。
• Direct α-C–H bond functionalization of unprotected cyclic amines
  作者：Weijie Chen、Longle Ma、Anirudra Paul、Daniel Seidel

  DOI：10.1038/nchem.2871

  日期：2018.2

  Direct α-C–H bond functionalization of unprotected cyclic amines Direct α-C–H bond functionalization of unprotected cyclic amines, Published online: 06 November 2017; doi:10.1038/nchem.2871NatureArticleSnippet(type=short-summary, markup= Cyclic amines bearing α-substituents are valuable building blocks for drug discovery and natural product synthesis. Introduction of α-substituents via site-selective

  未保护的环胺的直接α-C–H键官能化 未保护的环胺的直接α-C–H键官能化，在线发布：2017年11月6日；doi：10.1038 / nchem.2871NatureArticleSnippet（type = short-summary，markup = 带有α-取代基的环胺是药物发现和天然产物合成的重要组成部分。通过位点选择性取代C–H键引入α取代基极具吸引力，但通常仅限于受保护的胺底物。现在，基于操作上简单的氢化物转移的方法可以在未保护的胺上引入α取代基。，isJats = true）
• Facile One-Pot Parallel Synthesis of 3-Amino-1,2,4-triazoles
  作者：Andrey V. Bogolyubsky、Olena Savych、Anton V. Zhemera、Sergey E. Pipko、Alexander V. Grishchenko、Anzhelika I. Konovets、Roman O. Doroshchuk、Dmytro N. Khomenko、Volodymyr S. Brovarets、Yurii S. Moroz、Mykhailo Vybornyi

  DOI：10.1021/acscombsci.8b00060

  日期：2018.7.9

  strategy suitable for the quick preparation of a library of structurally diverse 1,2,4-triazoles in a one-pot setting. The key steps include the formation of thioureas followed by S-alkylation using 1,3-propane sultone and consecutive ring closure leading to the desired 1,2,4-triazoles. Parallel synthesis yields thousands of 1,2,4-triazoles in a cost- and time-efficient manner from commercially available

  1,2,4-三唑基序存在于许多商业化和研究性生物活性分子中。尽管它对于药物化学很重要，但缺乏针对该分子核心的便捷组合方法。在这里，我们提出一种合成策略，适合在一锅设置中快速制备结构多样的1,2,4-三唑库。关键步骤包括形成硫脲，然后使用1,3-丙烷磺酸内酯进行S-烷基化和连续闭环，从而得到所需的1,2,4-三唑。平行合成可从市售化学品中以节省成本和时间的方式产生数千个1,2,4-三唑。