1-hydroxy-4-methoxy-5-(methoxymethoxy)-2-naphthaldehyde | 1395924-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-4-methoxy-5-(methoxymethoxy)-2-naphthaldehyde
• 英文别名: 1-Hydroxy-4-methoxy-5-(methoxymethoxy)naphthalene-2-carbaldehyde；1-hydroxy-4-methoxy-5-(methoxymethoxy)naphthalene-2-carbaldehyde
• CAS: 1395924-02-3
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: HBYZZFNMGVWUAB-UHFFFAOYSA-N

物化性质

• 沸点：
  444.2±45.0 °C(predicted)
• 密度：
  1.282±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-4-methoxy-5-(methoxymethoxy)-2-naphthaldehyde 在 哌啶 、 borane dimethyl sulfide complex 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 63.08h， 生成 10,12-dimethoxy-1-(methoxymethoxy)-6-oxo-6H-dibenzo[c,h]chromene-8-carbaldehyde
  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 吡啶 、 氧气 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 copper(l) chloride 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 、 乙腈 为溶剂， 反应 34.58h， 生成 1-hydroxy-4-methoxy-5-(methoxymethoxy)-2-naphthaldehyde
  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.