(E)-ethyl 3-[3-(benzyloxy)-5-nitrophenyl]acrylate | 881422-35-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 3-[3-(benzyloxy)-5-nitrophenyl]acrylate
• 英文别名: ethyl (E)-3-(3-nitro-5-phenylmethoxyphenyl)prop-2-enoate
• CAS: 881422-35-1
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: ZDTOBSNFYCKSHT-CMDGGOBGSA-N

物化性质

• 沸点：
  495.3±40.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-[3-(benzyloxy)-5-nitrophenyl]acrylate 在 咪唑 、 碘 、 potassium diazodicarboxylate 、 二异丁基氢化铝 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 51.0h， 生成 Non-8-enoic acid [3-benzyloxy-5-((Z)-4-methyl-deca-3,9-dienyl)-phenyl]-amide
  参考文献：
  名称：

  A Versatile Approach toward the Ansamycin Antibiotics

  摘要：

  The ansamycin antibiotics contain metacyclophanic macrolactams, many of which possess potent antitumor activity. Only a few total syntheses of this family of natural products have been reported, and modifications to increase potency have not been described. Therefore, a method was developed to prepare the trienomycin A core via resin-bound triphenylphosphonium salts, which serve as both a reagent and a traceless linker to afford olefinic products that undergo ring-closing metathesis (RCM) to give macrocyclic scaffolds of varying ring sizes.

  DOI：

  10.1021/ol060022b
• 作为产物：
  描述：

  [3-(benzyloxy)-5-nitrophenyl]methanol 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-ethyl 3-[3-(benzyloxy)-5-nitrophenyl]acrylate
  参考文献：
  名称：

  A Versatile Approach toward the Ansamycin Antibiotics

  摘要：

  The ansamycin antibiotics contain metacyclophanic macrolactams, many of which possess potent antitumor activity. Only a few total syntheses of this family of natural products have been reported, and modifications to increase potency have not been described. Therefore, a method was developed to prepare the trienomycin A core via resin-bound triphenylphosphonium salts, which serve as both a reagent and a traceless linker to afford olefinic products that undergo ring-closing metathesis (RCM) to give macrocyclic scaffolds of varying ring sizes.

  DOI：

  10.1021/ol060022b