methyl (E)-3-(6H-naphtho[1,2-b]pyran-6-on-5-yl)acrylate | 1395923-92-8

• 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: methyl (E)-3-(6H-naphtho[1,2-b]pyran-6-on-5-yl)acrylate
• 英文别名: methyl (E)-3-(2-oxobenzo[h]chromen-3-yl)prop-2-enoate
• CAS: 1395923-92-8
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: URXYAOJYNCURBQ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(6H-naphtho[1,2-b]pyran-6-on-5-yl)acrylate 在 potassium hydroxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 53.0h， 生成 10-methoxy-6H-benzo[d]naphtho[1,2-b]pyran-6-one-8-carboxylic acid
  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
• 作为产物：
  描述：

  1-羟基-2-奈甲醛 、 戊烯二酸二甲酯 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到methyl (E)-3-(6H-naphtho[1,2-b]pyran-6-on-5-yl)acrylate
  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.