8-(hydroxymethyl)-10-methoxy-6H-benzo[d]naphtho[1,2-b]pyran | 1395924-10-3

• 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: 8-(hydroxymethyl)-10-methoxy-6H-benzo[d]naphtho[1,2-b]pyran
• 英文别名: (10-methoxy-6H-naphtho[1,2-c]isochromen-8-yl)methanol
• CAS: 1395924-10-3
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: MQRMGLRQZKXIFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-羟基-2-奈甲醛 在 哌啶 、 borane dimethyl sulfide complex 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 73.08h， 生成 8-(hydroxymethyl)-10-methoxy-6H-benzo[d]naphtho[1,2-b]pyran
  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.