2-氯-1-(5-甲基-噻吩-2-基)-乙酮 | 31772-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-1-(5-甲基-噻吩-2-基)-乙酮
• 中文别名: 2-氯-1-(5-甲基-2-噻吩基)乙酮
• 英文名称: 2-chloro-1-(5-methylthiophen-2-yl)ethan-1-one
• 英文别名: 2-Chloro-1-(5-methylthiophen-2-yl)ethanone
• CAS: 31772-42-6
• 化学式: C₇H₇ClOS
• mdl: MFCD00464874
• 分子量: 174.651
• InChiKey: IQLSTLPOEOWEOC-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42℃ (DEC.)
• 沸点：
  284℃
• 密度：
  1.264
• 闪点：
  126℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Chloro-1-(5-methyl-thiophen-2-yl)-ethanone
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-Chloro-1-(5-methyl-thiophen-2-yl)-ethanone
CAS number: 31772-42-6

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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: C7H7ClOS
Molecular weight: 174.6

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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, hydrogen chloride, 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-氯-1-(5-甲基-噻吩-2-基)-乙酮 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 3-(2,5-dimethylthiophen-3-yl)-4-[2-methyl-5-(2-methylthiazol-4-yl)thiophen-3-yl]furan-2,5-dione
  参考文献：
  名称：

  Synthesis and photochromic properties of dithienylmaleimides with sulfur-containing fragments

  摘要：

  合成了多种含硫二噻吩马来酰亚胺衍生物。对所得化合物的光谱和动力学特性进行了研究，结果表明合成的所有二噻吩乙烯均具有光致变色性能。

  DOI：

  10.1007/s11172-012-0295-z
• 作为产物：
  描述：

  2-lithio-5-methylthiophene 在 盐酸 、 乙醇 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 2-氯-1-(5-甲基-噻吩-2-基)-乙酮
  参考文献：
  名称：

  新型构件：1-Aryl-2-chloro-1-ethoxyethenes – 制备和转化

  摘要：

  我们在此描述了一种通过二氯乙醛二乙基缩醛与各种芳基和烯基锂化合物高产率反应制备 1-芳基-2-氯-1-乙氧基乙烯 2a-u（阿尔茨海默病的前药）的简单方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600863

文献信息

• 3-Haloquinolines by Friedländer Reaction of α-Haloketones
  作者：Sergey V. Ryabukhin、Vasiliy S. Naumchik、Andrey S. Plaskon、Oleksandr O. Grygorenko、Andrey A. Tolmachev

  DOI：10.1021/jo2008252

  日期：2011.7.15

  A general approach to 3-fluoro-, 3-chloro-, and 3-bromoquinolines which relies on organosilane-promoted Friedländer reaction of α-haloketones is described. The scope of the methylene component as well as influence of the organosilane component on the outcome of the reaction is studied. The method can be used under parallel synthesis conditions.

  描述了一种依赖于有机硅烷促进的α-卤代酮的Friedländer反应的3-氟，3-氯和3-溴喹啉的通用方法。研究了亚甲基组分的范围以及有机硅烷组分对反应结果的影响。该方法可以在平行合成条件下使用。
• An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Olena Savych、Sergey Pipko、Angelika Konovets、Maxim O. Platonov、Oleksandr V. Vasylchenko、Vasyl V. Hurmach、Oleksandr O. Grygorenko

  DOI：10.1021/acscombsci.7b00163

  日期：2018.1.8

  An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200–350, cLogP 1–3) was prepared. The success rate of the method was analyzed as a function of physicochemical parameters

  开发了一种通过原位生成的2,2,2-三氟乙基氨基甲酸酯与α-氨基酯反应平行合成乙内酰脲文库的方法。为了证明该方法的实用性，准备了根据铅样标准（MW 200–350，cLogP 1-3）设计的1158个乙内酰脲文库。分析了该方法的成功率与产品理化参数的关系，发现该方法可以被认为是用于铅导向合成的工具。通过合理设计，使用开发的方法进行平行合成，计算机模拟和体外筛选相结合的方法，发现了一种含乙内酰脲的超微摩尔主要分子，可作为Aurora激酶A抑制剂。
• Thienyl and Phenyl α-Halomethyl Ketones:  New Inhibitors of Glycogen Synthase Kinase (GSK-3β) from a Library of Compound Searching
  作者：Santiago Conde、Daniel I. Pérez、Ana Martínez、Concepción Perez、Francisco J. Moreno

  DOI：10.1021/jm034108b

  日期：2003.10.1

  (AD). Its inhibition is a valid approach to the treatment of AD. In this initial letter, some thienyl and phenyl alpha-halomethyl ketones are described as new non-ATP competitive inhibitors of GSK-3beta. They are considered as lead compounds for designing and synthesizing new series, to carry out SAR studies, clear up the mechanism of action, and, in general, evaluate their therapeutical usefulness.

  糖原合酶激酶（GSK-3beta）在阿尔茨海默氏病（AD）中起着至关重要的作用。它的抑制是治疗AD的有效方法。在此首封信中，一些噻吩基和苯基α-卤代甲基酮被描述为GSK-3beta的新型非ATP竞争性抑制剂。它们被认为是设计和合成新系列，进行SAR研究，阐明作用机理以及总体上评估其治疗用途的先导化合物。
• Compounds and their therapeutic use
  申请人：——

  公开号：US20030199508A1

  公开（公告）日：2003-10-23

  Compounds of formula I: 1 [wherein: X represents —CH═CH—, —CH═CR—, —CR═CR—, —CO—, —O—, —NH—, —NR—, S—, —SO—, —SO 2 —, —CH═N—, —CR═N—, —CH═N(O)—, —CR═N(O)— or any other atom or group of atoms capable of forming a S— or 6-membered heterocyclic ring; Y 1 , Y 2 and Y 3 independently represent hydrogen or halogen; R 1 , R 2 and R 3 are independently represent hydrogen, halogen, hydrocarbyl (—R), hydroxyl (—OH), hydrocarbyloxy (—O—R), mercapto (—SH), hydrocarbylthio (—S—R), hydrocarbylsulfinyl (—SO—R), hydrocarbylsulfonyl (—SO 2 —R), nitro (—NO 2 ), amino (—NH 2 ), hydrocarbylamino (—NHR), bis(hydrocarbyl)amino (—NR 2 ), hydrocarbylcarbonylamino (—NH—CO—R), cyano (—CN), carbamoyl (—CONH 2 ), hydrocarbylcarbarnoyl (—CONHR), bis(hydrocarbyl)carbamoyl (—CONR 2 ), carboxyl (—CO 2 H), hydrocarbyloxycarbonyl (—CO 2 R), formyl (—CHO), hydrocarbylcarbonyl (—COR), hydrocarbylcarbonyloxy (—OCOR), optionally substituted heteroaryl or optionally substituted heterocyclic; and the hydrocarbyl group R is a straight or branched chain hydrocarbyl group selected from alkyl, alkenyl, alkynyl, aryl, aralkyl, aralkenyl and aralkynyl, which may optionally be substituted by one or more substituents, selected from those defined above in relation to R1, R2 and R3]; are of use in the manufacture of a medicament for the treatment including prophylaxis of disease mediated by the activation of GSK-3.

  公式I的化合物：其中：X代表—CH₂CH—、—CH₂CR—、—CR₂CR—、—CO—、—O—、—NH—、—NR—、S—、—SO—、—SO₂—、—CH₂N—、—CR₂N—、—CH₂N(O)—、—CR₂N(O)—或任何其他能够形成S—或6元杂环的原子或原子团；Y₁、Y₂和Y₃独立地代表氢或卤素；R₁、R₂和R₃独立地代表氢、卤素、烃基（—R）、羟基（—OH）、烃氧基（—O—R）、巯基（—SH）、烃硫基（—S—R）、烃基磺基（—SO—R）、烃基磺酰基（—SO₂—R）、硝基（—NO₂）、氨基（—NH₂）、烃基氨基（—NHR）、双（烃基）氨基（—NR₂）、烃基羰基氨基（—NH—CO—R）、氰基（—CN）、氨基甲酰基（—CONH₂）、烃基甲酰胺基（—CONHR）、双（烃基）氨基甲酰基（—CONR₂）、羧基（—CO₂H）、烃氧羰基（—CO₂R）、甲酰基（—CHO）、烃基羰基（—COR）、烃基羰氧基（—OCOR）、可选地取代的杂芳烃或可选地取代的杂环；烃基R为直链或支链烃基，选自烷基、烯基、炔基、芳基、芳基烷基、芳基烯基和芳基炔基，该基团可以选择地被一个或多个取代基取代，所述取代基选自与R₁、R₂和R₃相关定义的那些取代基；用于制造一种药物，用于治疗包括预防GSK-3激活介导的疾病的药物。
• The Ir-Catalyzed Asymmetric Hydrogenation of α-Halogenated Ketones Utilizing Cinchona-Alkaloid-Derived NNP Ligand to Produce (<i>R</i>)- and (<i>S</i>)-Halohydrins
  作者：Qian Chen、Hao Sun、Linlin Li、Jie Tian、Qian Xu、Nana Ma、Li Li、Lin Zhang、Chun Li

  DOI：10.1021/acs.joc.2c02109

  日期：2022.12.2

  hydrogenation of α-halogenated ketones with iridium catalyst was developed, utilizing easily accessed cinchona-alkaloid-based NNP ligands. Various α-chloroacetophenones, heterocyclic thienyl and furanyl substrates, and even bromoketones were completely converted to the desired chiral halohydrins by this protocol. Both (R)- and (S)-chiral halohydrins can be prepared by changing the configurations of the chiral

  利用易于获取的基于金鸡纳生物碱的 NNP 配体，开发了铱催化剂对 α-卤化酮的不对称氢化。通过该协议，各种 α-氯苯乙酮、杂环噻吩基和呋喃基底物，甚至溴酮完全转化为所需的手性卤代醇。( R )- 和 ( S )- 手性卤代醇都可以通过改变手性配体 NNP 的构型来制备，分别具有高达 99.6% ee（对映体过量）和 98.8% ee。此外，有效地进行了克级实验。