4-(甲硫基)-3-硝基苯甲酸乙酯 | 1426841-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(甲硫基)-3-硝基苯甲酸乙酯
• 英文名称: Ethyl 4-methylsulfanyl-3-nitrobenzoate
• CAS: 1426841-88-4
• 化学式: C₁₀H₁₁NO₄S
• mdl: MFCD22575928
• 分子量: 241.268
• InChiKey: HAFQHPHGUHVBGV-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±32.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(甲硫基)-3-硝基苯甲酸乙酯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 [1-(4-Methylsulfonyl-3-nitrobenzoyl)piperidin-4-yl]-(4-phenylpiperidin-1-yl)methanone
  参考文献：
  名称：

  Synthesis and evaluation of methylsulfonylnitrobenzamides (MSNBAs) as inhibitors of the thyroid hormone receptor–coactivator interaction

  摘要：

  We previously identified the methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its obligate transcriptional coactivators and prevent thyroid hormone signaling. As part of our lead optimization work we demonstrated that sulfonylnitrophenylthiazoles (SNPTs), which replace the ester linkage of MSNBs with a thiazole, also inhibited coactivator binding to TR. Here we report that replacement of the ester with an amide (methylsulfonylnitrobenzamides, MSNBA) also provides active TR antagonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.055
• 作为产物：
  描述：

  4-氯-3-硝基苯甲酸乙酯 、 sodium thiomethoxide 以 四氢呋喃 为溶剂， 以94%的产率得到4-(甲硫基)-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  Synthesis and evaluation of methylsulfonylnitrobenzamides (MSNBAs) as inhibitors of the thyroid hormone receptor–coactivator interaction

  摘要：

  We previously identified the methylsulfonylnitrobenzoates (MSNBs) that block the interaction of the thyroid hormone receptor with its obligate transcriptional coactivators and prevent thyroid hormone signaling. As part of our lead optimization work we demonstrated that sulfonylnitrophenylthiazoles (SNPTs), which replace the ester linkage of MSNBs with a thiazole, also inhibited coactivator binding to TR. Here we report that replacement of the ester with an amide (methylsulfonylnitrobenzamides, MSNBA) also provides active TR antagonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.055