N-10-dimethoxy-N-methyl-6H-benzo[d]naphtho[1,2-b]-pyran-6-one-8-carboxamide | 1395924-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: N-10-dimethoxy-N-methyl-6H-benzo[d]naphtho[1,2-b]-pyran-6-one-8-carboxamide
• 英文别名: N,10-dimethoxy-N-methyl-6-oxonaphtho[1,2-c]isochromene-8-carboxamide
• CAS: 1395924-11-4
• 化学式: C₂₁H₁₇NO₅
• 分子量: 363.37
• InChiKey: AMXSYRGCCODETR-UHFFFAOYSA-N

物化性质

• 沸点：
  633.4±55.0 °C(predicted)
• 密度：
  1.329±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-羟基-2-奈甲醛 在 哌啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 79.0h， 生成 N-10-dimethoxy-N-methyl-6H-benzo[d]naphtho[1,2-b]-pyran-6-one-8-carboxamide
  参考文献：
  名称：

  An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues

  摘要：

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.

  DOI：

  10.1021/jo3012682

文献信息

• An Inverse Electron Demand Diels–Alder-Based Total Synthesis of Defucogilvocarcin V and Some C-8 Analogues
  作者：Penchal Reddy Nandaluru、Graham J. Bodwell

  DOI：10.1021/jo3012682

  日期：2012.9.21

  A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.