3-cyano-4-thiomethyl-6-(3-methoxyphenyl)-2H-pyran-2-one | 173484-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-cyano-4-thiomethyl-6-(3-methoxyphenyl)-2H-pyran-2-one
• 英文别名: 3-cyano-6-(3-methoxyphenyl)-4-methylthio-2-pyranone；6-(3-methoxyphenyl)-4-methylthio-2-oxo-2H-pyran-3-carbonitrile；6-(3-Methoxyphenyl)-4-methylsulfanyl-2-oxopyran-3-carbonitrile
• CAS: 173484-66-7
• 化学式: C₁₄H₁₁NO₃S
• 分子量: 273.312
• InChiKey: COFWYNUVSLOAAS-UHFFFAOYSA-N

物化性质

• 熔点：
  181-183 °C(Solv: methanol (67-56-1))
• 沸点：
  406.6±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3-cyano-4-thiomethyl-6-(3-methoxyphenyl)-2H-pyran-2-one 在 一水合肼 、 sodium t-butanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 11.0h， 生成 (Z)-2-[5-(3-Methoxy-phenyl)-1H-pyrazol-3-yl]-3-(1H-pyrrol-2-yl)-acrylonitrile
  参考文献：
  名称：

  Synthesis of E - and Z -Pyrazolylacrylonitriles and their evaluation as novel antioxidants

  摘要：

  A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-(pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitrile did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (H-1-, C-13-, H-1-H-1 COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure-activity relationship and to identify a lead compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00056-5
• 作为产物：
  描述：

  ethyl 2-cyano-3,3-bis(thiomethyl)propenoate 、 3-甲氧基苯乙酮 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以57%的产率得到3-cyano-4-thiomethyl-6-(3-methoxyphenyl)-2H-pyran-2-one
  参考文献：
  名称：

  Parmar, Virinder S.; Jain, Subhash C.; Jha, Amitabh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 10, p. 872 - 879

  摘要：

  DOI：

文献信息

• Synthesis and fluorescence of 2<i>h</i>-pyrone derivatives for organic light-emitting diodes (OLED)
  作者：Naoko Mizuyama、Yuka Murakami、Shinya Kohra、Kazuo Ueda、Kyoko Hiraoka、Yoshinori Tominaga、Junko Nagaoka、Kojiro Takahashi、Yasuhiro Shigemitsu

  DOI：10.1002/jhet.5570440120

  日期：2007.1

  2H-Pyrone derivatives were synthesized through the reaction of aryl acetyl compounds with ketene dithioacetals in the presence of sodium hydroxide, and they showed very strong fluorescence in the solid state. The light-emitting region of these 2H-pyrones is 447-630 nm in the solid states.

  2 H-吡喃酮衍生物是通过芳基乙酰基化合物与乙烯酮二硫缩醛在氢氧化钠的存在下反应合成的，它们在固态时显示出非常强的荧光。在固态下，这两个H-吡喃酮的发光区域为447-630 nm。
• 3-Cyano-6-(3-methoxyphenyl)-4-methylthio-2-pyranone
  作者：A. Kumar、N. Kumar、V. S. Parmar、W. Errington

  DOI：10.1107/s010827019500967x

  日期：1996.1.15

  In the crystal structure of the title compound, C14H11NO3S, the asymmetric unit consists of two molecules having different conformations. The main difference involves the orientation of the methoxy groups, but the angles between the two six-membered rings also differ slightly. This is the first reported structure of a delta-lactone with methylthio and cyano substituents.