7,8-dimethoxy-2-benzoxepin-3(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 7,8-dimethoxy-2-benzoxepin-3(1H)-one
• 英文别名: 7,8-dimethoxy-1H-2-benzoxepin-3-one
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: AVOMOIUBBRCWAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-溴藜芦醛 在 sodium tetrahydroborate 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 96.0h， 生成 7,8-dimethoxy-2-benzoxepin-3(1H)-one
  参考文献：
  名称：

  Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: facile synthesis of 2-benzoxepin-3(1H)-ones

  摘要：

  A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.050

文献信息

• Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: facile synthesis of 2-benzoxepin-3(1H)-ones
  作者：A. Gopi Krishna Reddy、J. Krishna、G. Satyanarayana

  DOI：10.1016/j.tet.2013.09.050

  日期：2013.11

  A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. (C) 2013 Elsevier Ltd. All rights reserved.