4-amino-3-(furan-2-carbonyl)-2-(methylsulfanyl)naphthalene-1-carbonitrile | 1616775-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-amino-3-(furan-2-carbonyl)-2-(methylsulfanyl)naphthalene-1-carbonitrile
• 英文别名: 4-Amino-3-(furan-2-carbonyl)-2-methylsulfanylnaphthalene-1-carbonitrile
• CAS: 1616775-88-2
• 化学式: C₁₇H₁₂N₂O₂S
• 分子量: 308.36
• InChiKey: BELDEBQZLMCOKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  alpha-氰基-邻-苯乙腈 、 1-(furan-2-yl)-3,3-bis(methylthio)prop-2-en-1-one 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以91%的产率得到4-amino-3-(furan-2-carbonyl)-2-(methylsulfanyl)naphthalene-1-carbonitrile
  参考文献：
  名称：

  Base mediated synthesis of α-aminated aroyl/acetylnaphthalenes through [4+2] annulations

  摘要：

  We have developed a base promoted simple, efficient and alternative approach for the synthesis of 4-amino-3-aroyl//heteroaroyl/acetyl-2-methylsulfanyl-naphthalene-1-carbonitriles by reaction of easily accessible 3,3-bis(methylthio)-1-aryl/heteroaryl/acetylprop-2-en-1-one and 2-cyanomethyl-benzonitrile. Reaction of 1-(2-halo/methoxy-phenyl)-3,3-bis(methylthio)prop-2-en-1-one and 2-cyanomethylbenzonitrile under basic conditions also afforded 6-(methylthio)-7-oxo-7,12-dihydrobenzo[c]acridine-5-carbonitrile along with usual product. Structure of the synthesized product has been confirmed by single X-ray crystallography. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.09.089

文献信息

• Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C–C bond formation strategy
  作者：Surjeet Singh、Pratik Yadav、Satya Narayan Sahu、Ismail Althagafi、Abhinav Kumar、Brijesh Kumar、Vishnu Ji Ram、Ramendra Pratap

  DOI：10.1039/c4ob00432a

  日期：——

  new precursor 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile has been synthesized by the reaction of 2-cyanomethylbenzonitrile, carbon disulfide and methyl iodide under basic conditions. The reaction of 2-(1-cyano-2,2-bis(methylthio)vinyl)benzonitrile with various functionalized aryl/heteroaryl methyl ketones or acetone under basic conditions afforded 4-amino-3-aroyl/heteroaroyl/acetyl-2-methylsul

  在碱性条件下，通过2-氰基甲基苄腈，二硫化碳和甲基碘的反应，合成了一种新的前体2-（1-氰基-2,2-双（甲硫基）乙烯基）苄腈。2-（1-氰基-2,2-双（甲硫基）乙烯基）苄腈与各种官能化的芳基/杂芳基甲基酮或丙酮在碱性条件下反应，得到4-氨基-3-芳酰基/杂芳酰基/乙酰基-2-甲基硫烷基萘通过（5C + 1C）环化策略获得高产率的-1-腈; 这涉及顺序的分子间，然后是分子内的CC键形成反应。产物的结构通过单晶X射线晶体学确认。