2-methyl-4-phenylthiophene | 16939-14-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-4-phenylthiophene
• 英文别名: 2-Methyl-4-phenyl-thiophen
• CAS: 16939-14-3
• 化学式: C₁₁H₁₀S
• 分子量: 174.266
• InChiKey: BVZZYUSNOQMZMS-UHFFFAOYSA-N

物化性质

• 熔点：
  73.5-73.7 °C(Solv: ethanol (64-17-5))
• 沸点：
  272-274 °C(Press: 750 Torr)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-4-phenylthiophene 在 氢氧化钾 、 正丁基锂 、 四甲基乙二胺 、 一水合肼 作用下， 以 乙醚 、 正己烷 、 二乙二醇二甲醚 、 水 为溶剂， 生成 2-methyl-8H-indeno[2,1-b]thiophene
  参考文献：
  名称：

  Efficient Method for the Synthesis of Hetarenoindanones Based on 3-Arylhetarenes and Their Conversion into Hetarenoindenes

  摘要：

  A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl NiV-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff-Kishner by hydrazine in the presence of KOH to the corresponding hetarenoindenes.

  DOI：

  10.1021/jo049504w
• 作为产物：
  描述：

  (E/Z)-2-phenylpent-2-ene 在 铁粉 、 sulfur 作用下， 生成 2-methyl-4-phenylthiophene
  参考文献：
  名称：

  Woronkow; Broun, Zhurnal Obshchei Khimii, 1948, vol. 18, p. 70,74

  摘要：

  DOI：

文献信息

• γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and Their Application to the Preparation of Five-Membered Ring Heterocycles
  作者：Mei-Huey Lin、Yen-Chih Huang、Chung-Kai Kuo、Chang-Hsien Tsai、Yi-Syuan Li、Ting-Chia Hu、Tsung-Hsun Chuang

  DOI：10.1021/jo5001274

  日期：2014.3.21

  A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered

  已开发出一种简单的方法来合成γ-卤代烯酮。该方法采用的序列涉及初始的铟介导的苯甲酰卤与炔丙基溴的烯丙基化反应。该过程之后是形成的高烯丙基卤代醇的酸促进的重排反应。可以将新方法结合到有效合成各种五元杂环化合物的途径中。
• Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4-Selective CH Arylation Enabled by Boronic Acids
  作者：Sylvia Kirchberg、Satoshi Tani、Kirika Ueda、Junichiro Yamaguchi、Armido Studer、Kenichiro Itami

  DOI：10.1002/anie.201007060

  日期：2011.3.1

  It adds up to 4! Thiophenes and thiazoles can be arylated in the 4‐ rather than the expected 5‐position in a new CH functionalization reaction (see scheme; TEMPO: 2,2,6,6‐tetramethylpiperidine‐N‐oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment

  总计为4！噻吩和噻唑可以在新的CH官能化反应中的4位而不是预期的5位芳基化（请参阅方案； TEMPO：2,2,6,6-四甲基哌啶-N-氧基）。硼酸被证明是实现否则很难的C4选择性的关键。该方法被用于关键药理结构的简明合成，具有治疗阿尔茨海默氏病的潜力。
• [EN] PIPERIDINE-CONTAINING COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS CONTENANT DE LA PIPÉRIDINE ET LEURS UTILISATIONS
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010080864A1

  公开（公告）日：2010-07-15

  A method for preventing and/or treating a metabolic disease, cerebrovascular disease, etc. which comprises administering to a mammal an effective amount of the compound of the formula (I) wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof. And a novel compound of the formula (I-1): wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof has an anti-diabetic effect and a neuroprotective effect. Accordingly, the compound of the formula (I) and the compound of the formula (I-1) are useful in a method for preventing and/or treating for a metabolic disease such as diabetes, cerebrovascular disease such as stroke, etc.

  一种预防和/或治疗代谢性疾病、脑血管疾病等的方法，包括向哺乳动物施用化合物的有效量，其化学式为(I)，其中所有符号的含义与规范中定义的相同；其盐、N-氧化物、溶剂合物或前药。以及化学式(I-1)的新化合物：其中所有符号的含义与规范中定义的相同；其盐、N-氧化物、溶剂合物或前药具有抗糖尿病作用和神经保护作用。因此，化合物(I)和化合物(I-1)在预防和/或治疗代谢性疾病如糖尿病、脑血管疾病如中风等方面是有用的。
• Benzenesulfonyl chlorides: new reagents for access to alternative regioisomers in palladium-catalysed direct arylations of thiophenes
  作者：Kedong Yuan、Henri Doucet

  DOI：10.1039/c3sc52420e

  日期：——

  The palladium-catalysed coupling of benzenesulfonyl chlorides with thiophene derivatives allows regioselective access to β-arylated thiophenes. The reaction proceeds with easily accessible catalyst, base and substrates, without oxidant or ligand and tolerates a variety of substituents on both the benzene and thiophene moieties.

  钯催化的苯磺酰氯与噻吩衍生物的偶联使区域选择性地进入β-芳基噻吩。该反应在容易获得的催化剂，碱和底物的情况下进行，没有氧化剂或配体，并且在苯和噻吩部分上均具有多种取代基。
• Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones
  作者：Zhen-Kang Wen、Ting-Ting Song、Yu-Fang Liu、Jian-Bin Chao

  DOI：10.1039/c8cc01059e

  日期：——

  Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C–H functionalization under mild reaction conditions is

  由于竞争性的酮脱氢和共轭加成，环状烯酮与杂芳烃的脱氢偶联一直是一个长期的挑战。在本文中，报道了在温和的反应条件下，不同大小的环状烯酮与取代的噻吩的脱氢偶联反应，通过钯催化的CH-H官能化反应，构建β-噻吩环状烯酮化合物。具有不同官能团的简单取代的噻吩可以直接引入到环烯酮中，在噻吩部分的α位置具有主要的区域选择性，并且具有出色的官能团耐受性。还已经证明了偶联产物向合成有用的间-杂芳基化的苯酚衍生物的进一步的分子转化。