6-(4-methoxyphenyl)-5-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile | 198135-56-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-methoxyphenyl)-5-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 6-(4-methoxyphenyl)-5-methyl-4-(methylsulfanyl)-2-oxo-2H-pyran-3-carbonitrile；6-(4-methoxyphenyl)-5-methyl-4-methylsulfanyl-2-oxopyran-3-carbonitrile
• CAS: 198135-56-7
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: BVNAIKKJMXBBDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)-5-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile 在 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2-(6-isopropyl-4-(4-methoxyphenyl)-3-methyl-5-phenyl-2H-pyran-2-ylidene)acetonitrile
  参考文献：
  名称：

  优先氧气支架合成的面向多样性的通用协议：吡喃酮，香豆素，苯并香豆素和萘香豆素†

  摘要：

  一种新的合成各种功能化特权氧杂环骨架的通用方法，即。开发了吡喃酮，香豆素和苯甲酰香豆素。合成过程是通过碳负离子诱导的内酯与各种亚甲基羰基化合物的环转化，然后由DDQ介导的氧杂亚砜中间体的氧化裂解而实现的。研究在DDQ存在下将草酰亚烷基中间体转化为相应的羰基化合物的机理表明，该反应是通过形成迈克尔加合物而不是分子间电荷转移复合物。该方法提供了对氧杂环分子框架上的许多官能团具有耐受性的多种特权支架的制造。

  DOI：

  10.1039/c3ob40859k
• 作为产物：
  描述：

  3,3-双(甲硫基)-2-氰基丙烯酸乙酯 、 对甲氧基苯丙酮 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 6-(4-methoxyphenyl)-5-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile
  参考文献：
  名称：

  通过新型CC键形成反应的功能性联苯芳基的区域选择性合成

  摘要：

  通过吸电子或供电子取代基官能化的不对称联芳基的快速合成方法得到了描述，并通过羰基诱导的2 H-吡喃-2-酮与丙二腈的极佳收率进行了环转化。

  DOI：

  10.1016/j.tetlet.2005.06.034

文献信息

• A Metal-Free Approach for the Synthesis of 2-Tetralones via Carbanion-Induced Ring Transformation of 2H-Pyran-2-ones
  作者：Fateh Singh、Samata Shetgaonkar

  DOI：10.1055/s-0036-1591591

  日期：2018.9

  economical and tolerates a wide range of functional groups. A metal-free, ultrasound-assisted approach for the synthesis of highly functionalized 2-tetralones in high yields is described. The process involves ring transformation of 2H-pyran-2-ones with the spirocyclic ketone 1,4-cyclohexandione monoethylene ketal to yield spiro­cyclic ketals and subsequent acid-mediated hydrolysis. This protocol is free from

  摘要 描述了一种无金属，超声辅助的高产率合成高度功能化的2-四氢萘酮的方法。该方法涉及用螺环酮1，4-环己二酮单亚乙基缩酮对2 H-吡喃-2-酮进行环转化，以产生螺环缩酮，然后进行酸介导的水解。该方案不含任何有机金属试剂，经济且可耐受多种官能团。 描述了一种无金属，超声辅助的高产率合成高度功能化的2-四氢萘酮的方法。该方法涉及用螺环酮1，4-环己二酮单亚乙基缩酮对2 H-吡喃-2-酮进行环转化，以产生螺环缩酮，然后进行酸介导的水解。该方案不含任何有机金属试剂，经济且可耐受多种官能团。
• Regioselective synthesis of 2-amino-isophthalonitriles through a ring transformation strategy
  作者：Fateh V. Singh、Vijay Kumar、Brijesh Kumar、Atul Goel

  DOI：10.1016/j.tet.2007.08.056

  日期：2007.11

  An expeditious synthesis of several 2-amino-isophthalonitriles and their biaryl compounds is described and illustrated by carbanion-induced ring transformation of functionalized 2H-pyran-2-ones with malononitrile in excellent yields. The strength of the reaction lies in the creation of an aromatic ring at room temperature from six-membered lactones under mild reaction conditions. This approach is an

  描述了几种2-氨基-间苯二甲腈及其联芳基化合物的快速合成方法，并通过羰基诱导的官能化的2 H-吡喃-2-酮与丙二腈的极高收率进行了环转化。反应的强度在于在室温下由六元内酯在温和的反应条件下产生芳环。该方法是2 H-吡喃-2-酮与亲二烯物的Diels-Alder反应的替代方法，后者需要强制加热条件才能获得苯衍生物。
• Arylanthranilodinitriles: A new biaryl class of antileishmanial agents
  作者：Fateh V. Singh、Rit Vatsyayan、Uma Roy、Atul Goel

  DOI：10.1016/j.bmcl.2006.02.012

  日期：2006.5

  A series of anthranilodinitrile-based biaryls were synthesized and evaluated in vitro against extracellular promastigotes and intracellular amastigotes of Leishmania donovani. Among various screened compounds, a biaryl with trifluoromethyl group 5f showed 83% inhibition against promastigotes and 70% inhibition against amastigotes of L. donovani at 8 and 20 mu g/mL concentrations, respectively. (C) 2006 Elsevier Ltd. All rights reserved.
• 3-Cyano-6-(4-methoxyphenyl)-5-methyl-4-methylthio-2<i>H</i>-pyran-2-one
  作者：A. Azim、V. S. Parmar、W. Errington

  DOI：10.1107/s0108270197007336

  日期：1997.10.15

  In the title compound, C15H13NO3S, the two six-membered rings are inclined at an angle of 38.9(1)degrees. The conformations of the ring substituents are discussed and compared with the situation when the 5-methyl substituent is replaced with an H atom.
• 5,6-Diarylanthranilo-1,3-dinitriles as a new class of antihyperglycemic agents
  作者：Fateh V. Singh、Amrita Parihar、Sumit Chaurasia、Amar B. Singh、Salil P. Singh、Akhilesh K. Tamrakar、Arvind K. Srivastava、Atul Goel

  DOI：10.1016/j.bmcl.2009.02.118

  日期：2009.4

  Various functionalized mono- and diarylanthranilo-1,3-dinitriles were synthesized and evaluated for their in vitro antihyperglycemic activity against the PTP-1B, glucose-6-phosphatase, glycogen phosphorylase and alpha-glucosidase enzymes. Among various screened compounds, 5,6-diaryl substituted anthranilo1,3-dinitriles 3a, 3b, and 3d showed good inhibitory activity against PTP-1B with IC50 values of 58 72 mu M. Three of the test compounds showed significant (25-37%) lowering of plasma glucose level at 24 h in sucrose-challenged streptozotocin-induced diabetic Sprague-Dawley rat model. (C) 2009 Elsevier Ltd. All rights reserved.