8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]naphtho[1,2-b]pyran-6-one-8-carboxylic acid | 1395924-07-8

• 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: 8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]naphtho[1,2-b]pyran-6-one-8-carboxylic acid
• 英文别名: 8-(Hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)naphtho[1,2-c]isochromen-6-one；8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)naphtho[1,2-c]isochromen-6-one
• CAS: 1395924-07-8
• 化学式: C₂₂H₂₀O₇
• 分子量: 396.397
• InChiKey: TYSVXECNYPFRCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)-6H-benzo[d]naphtho[1,2-b]pyran-6-one-8-carboxylic acid 在 三氯化硼 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-hydroxy-10,12-dimethoxy-6H-benzo[d]naphtho[1,2-b]-pyran-6-one-8-carboxaldehyde
  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：

  1,5-二羟基萘 在 哌啶 、 吡啶 、 borane dimethyl sulfide complex 、 氧气 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 copper(l) chloride 、 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 94.66h， 生成 8-(hydroxymethyl)-10,12-dimethoxy-1-(methoxymethoxy)-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

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.