6-methoxynaphthalene-1(2H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxynaphthalene-1(2H)-one
• 英文别名: 6-methoxy-1-naphthalenone；Ethyl (2E)-2-acetyl-3-(3,4-dichloroanilino)-2-propenoate；6-methoxy-2H-naphthalen-1-one
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: ZICHDXOPCVTBMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxynaphthalene-1(2H)-one 、 2,3-二氯-5,6-二氰基-1,4-苯醌 以 乙腈 为溶剂， 以28%的产率得到7-methoxynaphtho[1,2-b]furan-2,3-dicarbonitrile
  参考文献：
  名称：

  DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)

  摘要：

  A facile oxidative coupling of alpha-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available beta-diketones, simple ketones, and beta-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.

  DOI：

  10.1021/jo4026034

文献信息

• Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction
  作者：Fang Fang、Jie Xia、Siying Quan、Shanping Chen、Guo-Jun Deng

  DOI：10.1021/acs.joc.3c01700

  日期：2023.10.20

  A facile and practical approach for the preparation of substituted pyrimidines from ketones, NH4OAc, and N,N-dimethylformamide dimethyl acetal has been described. This NH4I-promoted three-component tandem reaction affords a broad range of substituted pyrimidines in acceptable yields under metal- and solvent-free conditions. The present methodology features the advantages of simple and easily available

  已经描述了由酮、NH 4 OAc和N , N-二甲基甲酰胺二甲基缩醛制备取代嘧啶的简单且实用的方法。这种 NH 4 I 促进的三组分串联反应在无金属和无溶剂的条件下以可接受的产率提供了多种取代的嘧啶。该方法具有起始原料简单易得、无金属和溶剂条件、底物范围广、官能团耐受性好以及克级合成等优点。
• DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene)
  作者：Zheng-Lin Wang、Hong-Liang Li、Li-Shi Ge、Xing-Lan An、Zi-Gang Zhang、Xiaoyan Luo、John S. Fossey、Wei-Ping Deng

  DOI：10.1021/jo4026034

  日期：2014.2.7

  A facile oxidative coupling of alpha-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available beta-diketones, simple ketones, and beta-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.