4-methyloxy-2,5-dihydrothiophene-3-carbonitrile | 146496-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 4-methyloxy-2,5-dihydrothiophene-3-carbonitrile
• 英文别名: 4-Methoxy-2,5-dihydrothiophene-3-carbonitrile
• CAS: 146496-38-0
• 化学式: C₆H₇NOS
• 分子量: 141.194
• InChiKey: HBSHLXJYUZWGJL-UHFFFAOYSA-N

物化性质

• 沸点：
  350.8±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyloxy-2,5-dihydrothiophene-3-carbonitrile 在 N-溴代丁二酰亚胺(NBS) 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 2-bromo-4-cyano-3-methoxythiophene
  参考文献：
  名称：

  Facile Synthesis of 3-Alkoxy-4-cyanothiophenes As New Building Blocks for Donor−Acceptor Conjugated Systems

  摘要：

  3-Alkoxy-4-cyanothiophenes are efficiently synthesized in two steps from the readily available 4-cyano-3-oxotetrahydrothiophene. Regioisomers of bithiophene derivatives are easily synthesized by playing on the strong electronic dissymmetry of the thiophene ring induced by the alkoxy and cyano groups.

  DOI：

  10.1021/ol200296j
• 作为产物：
  描述：

  4-氰基-3-四氢噻吩酮 、 三氟甲烷磺酸甲酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以55%的产率得到4-methyloxy-2,5-dihydrothiophene-3-carbonitrile
  参考文献：
  名称：

  Facile Synthesis of 3-Alkoxy-4-cyanothiophenes As New Building Blocks for Donor−Acceptor Conjugated Systems

  摘要：

  3-Alkoxy-4-cyanothiophenes are efficiently synthesized in two steps from the readily available 4-cyano-3-oxotetrahydrothiophene. Regioisomers of bithiophene derivatives are easily synthesized by playing on the strong electronic dissymmetry of the thiophene ring induced by the alkoxy and cyano groups.

  DOI：

  10.1021/ol200296j

文献信息

• Competition for regiochemical control between substituents of some 2,3-disubstituted buta-1,3-dienes in the Diels–Alder reactions
  作者：Ta-Shue Chou、Chin-Yao Chang、Meng-Chu Wu、Shao-Hwa Hung、Hui-Ming Liu、Wen-Yuan Yeh

  DOI：10.1039/c39920001643

  日期：——

  Several 3,4-disubstituted 3-sulfolenes 1a–j, the precursors for the corresponding 2,3-disubstituted 1,3-dienes 2a–j, are conveniently prepared and undergo Diels–Alder reactions smoothly with methyl acrylate under thermal conditions where the order of para-directing ability of different substituents is OTBS≃CN > SPh > OMe≃CO2Me > OTs > OAc.

  几种 3,4-二取代的 3-亚砜 1aâj 是相应的 2,3-二取代的 1,3-二烯 2aâj 的前体，可以方便地制备，并在热条件下与丙烯酸甲酯顺利进行 DielsâAlder 反应，不同取代基的对位定向能力顺序为 OTBSâCN > SPh > OMeâCO2Me > OTs > OAc。
• [EN] A WEAK ELECTRON-DONATING BUILDING BLOCK, COPOLYMERS THEREOF AND THEIR PREPARATION METHODS AS WELL AS THEIR APPLICATIONS<br/>[FR] ÉLÉMENT STRUCTURAL FAIBLE DONNEUR D'ÉLECTRONS, COPOLYMÈRES DE CEUX-CI ET LEURS PROCÉDÉS DE PRÉPARATION ET APPLICATIONS
  申请人：UNIV SOUTH SCIENCE & TECHNOLOGY CHINA

  公开号：WO2018076247A1

  公开（公告）日：2018-05-03

  A weak electron-donating building block, copolymers thereof and their preparation methods as well as their applications. The weak electron-donating building block provided by the present invention is of Formula I. In the present invention, incorporating strong electron-withdrawing substituents into the electron-rich 3, 3' -dialkyoxy-2, 2' -bithiophene leads to new monomers with weaker electron donating abilities and hence lower-lying HOMOs.