6-(4-Chloro-phenyl)-5-methyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile | 864370-34-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(4-Chloro-phenyl)-5-methyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile
• 英文别名: 6-(4-Chlorophenyl)-5-methyl-4-methylsulfanyl-2-oxopyran-3-carbonitrile；6-(4-chlorophenyl)-5-methyl-4-methylsulfanyl-2-oxopyran-3-carbonitrile
• CAS: 864370-34-3
• 化学式: C₁₄H₁₀ClNO₂S
• 分子量: 291.758
• InChiKey: SCDFIYDIYWWORM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-Chloro-phenyl)-5-methyl-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile 在 氢氧化钾 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-amino-4'-chloro-6-methyl-5-piperidin-1-yl-biphenyl-2,4-dicarbonitrile
  参考文献：
  名称：

  通过环转化策略区域选择性合成2-氨基-间苯二甲腈

  摘要：

  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。

  DOI：

  10.1016/j.tet.2007.08.056
• 作为产物：
  描述：

  4-氯苯丙酮 、 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， 生成 6-(4-Chloro-phenyl)-5-methyl-4-methylsulfanyl-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 functionally congested biaryls through a novel C–C bond formation reaction
  作者：Atul Goel、Fateh Veer Singh

  DOI：10.1016/j.tetlet.2005.06.034

  日期：2005.8

  An expeditious synthesis of unsymmetrical biaryls functionalized with electron-withdrawing or -donating substituents is described and illustrated by the carbanion-induced ring transformation of 2H-pyran-2-ones with malononitrile in excellent yields.

  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。
• 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.
• 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.
• 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。
• Base-mediated alternate route for multi-functionalized allylbenzenes using ring transformation strategy
  作者：Samata E. Shetgaonkar、Fateh V. Singh

  DOI：10.1080/00397911.2020.1782430

  日期：2020.8.17

  Abstract A simple yet innovative approach for the construction of multi-substituted allylbenzenes 14, 16 and 18 with ‘donor-acceptor’ functionalities has been delineated through base-mediated ring transformation of 6-aryl-2H-pyran-2-ones 13, 15 and 17 respectively with commercially available 5-hexen-2-one 11 as carbanion source. The reactions were carried out at room temperature without using any catalyst

  摘要 通过碱基介导的 6-芳基-2H-吡喃-2-酮 13、15 环转化，描述了一种简单而创新的方法，用于构建具有“供体-受体”功能的多取代烯丙基苯 14、16 和 18和 17 分别以市售的 5-hexen-2-one 11 作为碳负离子源。反应在室温下进行，不使用任何具有优异官能团耐受性的催化剂或有机金属试剂。此外，除了通常的金属催化交叉偶联反应之外，本方法是获得烯丙基苯的可能替代途径。图形概要