5-(3,4-dimethoxyphenyl)-6-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile | 136358-76-4

• 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: 5-(3,4-dimethoxyphenyl)-6-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 5-(3,4-Dimethoxyphenyl)-6-methyl-4-methylsulfanyl-2-oxopyran-3-carbonitrile
• CAS: 136358-76-4
• 化学式: C₁₆H₁₅NO₄S
• 分子量: 317.365
• InChiKey: OTNYOUYQEWXREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxyphenyl)-6-methyl-4-(methylthio)-2-oxo-2H-pyran-3-carbonitrile 在 吡啶 、 一水合肼 作用下， 反应 4.0h， 以65%的产率得到[4-(3,4-Dimethoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-acetonitrile
  参考文献：
  名称：

  Ram, Vishnu Ji; Verma, Monika; Hussaini, Falak Anwer, Liebigs Annalen der Chemie, 1991, # 11, p. 1229 - 1231

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酮 、 3,3-双(甲硫基)-2-氰基丙烯酸乙酯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以84%的产率得到5-(3,4-dimethoxyphenyl)-6-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

• 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.
• Ram, Vishnu Ji; Haque, Navedul; Singh, Sanjay Kumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 9, p. 924 - 928
  作者：Ram, Vishnu Ji、Haque, Navedul、Singh, Sanjay Kumar、Hussaini, Falak Anwer、Shoeb, Aboo

  DOI：——

  日期：——
• Hussaini, Falak A.; Pragya; Ram, Vishnu J., Journal of Chemical Research, Miniprint, 1994, # 3, p. 533 - 540
  作者：Hussaini, Falak A.、Pragya、Ram, Vishnu J.、Singh, Sunil K.、Nath, Mahendra、et al.

  DOI：——

  日期：——
• A vicarious synthesis of unsymmetrical meta- and para- terphenyls from 2H-pyran-2-ones
  作者：Atul Goel、Deepti Verma、Fateh Veer Singh

  DOI：10.1016/j.tetlet.2005.10.018

  日期：2005.12

  An innovative synthesis of terphenyls functionalized with electron-withdrawing or -donating substituents is described and illustrated by carbanion-induced ring transformation of 2H-pyran-2-ones with 2-methoxyacetophenone in excellent yields. The existing protocols for the synthesis of terplienyls are generally inter- and intramolecular aryl-aryl cross couplings in the presence of metal complexes. In this letter, we report a potentially useful alternative to conventional metal-catalyzed cross-coupling reactions. (c) 2005 Elsevier Ltd. All rights reserved.