ethyl (3-(benzo[d][1,3]dioxol-5-yl)-3-(methylthio)-2-(thiophene-2-carboxamido)acryloyl)-L-phenylalaninate | 1446782-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (3-(benzo[d][1,3]dioxol-5-yl)-3-(methylthio)-2-(thiophene-2-carboxamido)acryloyl)-L-phenylalaninate
• CAS: 1446782-47-3
• 化学式: C₂₇H₂₆N₂O₆S₂
• 分子量: 538.645
• InChiKey: BABHCDSTWQNAGI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl (3-(benzo[d][1,3]dioxol-5-yl)-3-(methylthio)-2-(thiophene-2-carboxamido)acryloyl)-L-phenylalaninate 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到(2S)-ethyl 2-(5-(benzo[d][1,3]dioxol-5-yl)-2-(thiophen-2-yl)-thiazole-4-carboxamido)-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson’s Reagent-Mediated Chemoselective Thionation–Cyclization of Functionalized Enamides

  摘要：

  An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.

  DOI：

  10.1021/jo401208u
• 作为产物：
  描述：

  4-[benzo[d][1,3]dioxol-5-yl(methylthio)methylene]-2-(2-thienyl)oxazol-5(4H)-one 、 (2S)-2-氨基-3-苯丙酸乙酯 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以75%的产率得到ethyl (3-(benzo[d][1,3]dioxol-5-yl)-3-(methylthio)-2-(thiophene-2-carboxamido)acryloyl)-L-phenylalaninate
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson’s Reagent-Mediated Chemoselective Thionation–Cyclization of Functionalized Enamides

  摘要：

  An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.

  DOI：

  10.1021/jo401208u