N,N-Diisopropyl-2'-(methoxymethoxy)-3,4-dimethoxy-2-biphenylcarboxamide | 133730-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-Diisopropyl-2'-(methoxymethoxy)-3,4-dimethoxy-2-biphenylcarboxamide
• 英文别名: 2,3-dimethoxy-6-[2-(methoxymethoxy)phenyl]-N,N-di(propan-2-yl)benzamide
• CAS: 133730-26-4
• 化学式: C₂₃H₃₁NO₅
• 分子量: 401.503
• InChiKey: ODNMMIXBLOTTBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,N-Diisopropyl-2'-(methoxymethoxy)-3,4-dimethoxy-2-biphenylcarboxamide 在 三溴化硼 、 溶剂黄146 作用下， 生成 7,8-Dihydroxy-6H-dibenzopyran-6-one
  参考文献：
  名称：

  Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid

  摘要：

  A general regiospecific synthesis of dibenzo[b,d]pyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7. BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8. In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.

  DOI：

  10.1021/jo00012a004
• 作为产物：
  描述：

  1-溴-2-(甲氧基甲氧基)苯 、 2-N,N-diisopropylcarboxamido-3,4-dimethoxyphenyl boronic acid 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 18.0h， 以71%的产率得到N,N-Diisopropyl-2'-(methoxymethoxy)-3,4-dimethoxy-2-biphenylcarboxamide
  参考文献：
  名称：

  Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid

  摘要：

  A general regiospecific synthesis of dibenzo[b,d]pyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7. BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8. In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.

  DOI：

  10.1021/jo00012a004

文献信息

• ALO, B. I.;KANDIL, A.;PATIL, P. A.;SHARP, M. J.;SIDDIGUI, M. A.;SNIECKUS,+, J. ORG. CHEM., 56,(1991) N2, C. 3763-3768
  作者：ALO, B. I.、KANDIL, A.、PATIL, P. A.、SHARP, M. J.、SIDDIGUI, M. A.、SNIECKUS,+

  DOI：——

  日期：——