3-chloro-N-(cyanomethyl)-N-methylbenzamide | 199278-08-5

• 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: 3-chloro-N-(cyanomethyl)-N-methylbenzamide
• CAS: 199278-08-5
• 化学式: C₁₀H₉ClN₂O
• 分子量: 208.647
• InChiKey: OCHWHYHXDVDTSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  392.7±27.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(cyanomethyl)-N-methylbenzamide 在 aluminum selenide 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-Chloro-N-methyl-N-selenocarbamoylmethyl-benzamide
  参考文献：
  名称：

  Design, synthesis and glutathione peroxidase-Like properties of ovothiol-Derived diselenides

  摘要：

  Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00504-2
• 作为产物：
  描述：

  3-氯苯甲酰氯 、 甲氨基乙腈盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3-chloro-N-(cyanomethyl)-N-methylbenzamide
  参考文献：
  名称：

  Design, synthesis and antioxidant properties of ovothiol-derived 4-mercaptoimidazoles

  摘要：

  从天然抗氧化剂家族——卵泡硫醇中衍生出的14种4-巯基咪唑，已通过硫代酰胺与三甲基硅基三氟甲磺酸酯（三氟甲磺酸盐）的环化反应合成。这些化合物已进行了其自由基清除活性的测定。

  DOI：

  10.1039/a703741d

文献信息

• Design, synthesis and antioxidant properties of ovothiol-derived 4-mercaptoimidazoles
  作者：Vincent Zoete、Fabrice Bailly、Jean-Pierre Catteau、Jean-Luc Bernier

  DOI：10.1039/a703741d

  日期：——

  Fourteen 4-mercaptoimidazoles derived from the naturally occurring family of antioxidants, the ovothiols, have been synthesized by cyclization of thioamides with trimethylsilyl trifluoromethanesulfonate (triflate). These compounds have been assayed for their radical-scavenging activity.

  从天然抗氧化剂家族——卵泡硫醇中衍生出的14种4-巯基咪唑，已通过硫代酰胺与三甲基硅基三氟甲磺酸酯（三氟甲磺酸盐）的环化反应合成。这些化合物已进行了其自由基清除活性的测定。
• Design, synthesis and glutathione peroxidase-Like properties of ovothiol-Derived diselenides
  作者：Fabrice Bailly、Nathalie Azaroual、Jean-Luc Bernier

  DOI：10.1016/s0968-0896(03)00504-2

  日期：2003.10

  Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione. (C) 2003 Elsevier Ltd. All rights reserved.