prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-formyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate | 957714-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-formyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
• CAS: 957714-66-8
• 化学式: C₂₄H₂₆BrNO₇
• 分子量: 520.377
• InChiKey: RMQQWLXZZUETMM-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-formyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate 、 甲基三苯基溴化膦 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以52%的产率得到prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2R,3S)-2-ethenyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g
• 作为产物：
  描述：

  prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-(hydroxymethyl)-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以79%的产率得到prop-2-enyl N-[(4-bromophenyl)methyl]-N-[(2S,3S)-2-formyl-6-(2-methoxyethoxymethoxy)-2,3-dihydro-1-benzofuran-3-yl]carbamate
  参考文献：
  名称：

  Benzofuran-Derived Cyclic β-Amino Acid Scaffold for Building a Diverse Set of Flavonoid-Like Probes and the Discovery of a Cell Motility Inhibitor

  摘要：

  We report here a practical, enantioselective synthesis of benzofuran-derived, cyclic trans-beta-amino acid scaffold. In two cases, tricyclic derivatives having six- and eight-membered unsaturated lactams were obtained from this versatile scaffold. To explore the biological applications, these compounds were subjected to cell-based assays, using NIH3T3 mouse cells to examine their potency as cell motility inhibitors and identified 18 as a potent cell motility inhibitor (IC(50) approximate to 40 mu M in chamber cell migration assay).

  DOI：

  10.1021/ol800050g