6-Hydroxy-4-methyl-1H-naphth<2.1-d><1.3>oxazin-3(3H)-one | 157528-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Hydroxy-4-methyl-1H-naphth<2.1-d><1.3>oxazin-3(3H)-one
• 英文别名: 6-hydroxy-4-methyl-1H-benzo[f][3,1]benzoxazin-3-one
• CAS: 157528-27-3
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: GJNABDZNYICZJI-UHFFFAOYSA-N

物化性质

• 沸点：
  448.7±45.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-4-methyl-1H-naphth<2.1-d><1.3>oxazin-3(3H)-one 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到2-(甲基氨基)萘-1,4-二酮
  参考文献：
  名称：

  p-Quinonemethide Analog of the CC-1065 and Duocarmycin Alkylation Subunits

  摘要：

  The synthesis and preliminary evaluation of 10 and 11, stable precursors to the inherently reactive but isolable p-quinonemethide analog 9 of the CC-1065 and duocarmycin alkylation subunits, are detailed. The p-quinonemethide 9, while reactive (t(1/2) < 1 min, CH3OH), represents one of the few unsubstituted quinonemethides sufficiently stable for isolation and characterization. The structural origin of this stability and the ramifications of the observations on the origin of the stability of the CC-1065 and duocarmycin alkylation subunits are discussed.

  DOI：

  10.1021/jo00096a043
• 作为产物：
  描述：

  Methyl 2--4-(benzyloxy)-1-naphthalenecarboxylate 在 palladium on activated charcoal 、 9-硼杂双环[3.3.1]壬基三氟甲磺酸酯 咪唑 、 lithium hydroxide 、 氢气 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.92h， 生成 6-Hydroxy-4-methyl-1H-naphth<2.1-d><1.3>oxazin-3(3H)-one
  参考文献：
  名称：

  p-Quinonemethide Analog of the CC-1065 and Duocarmycin Alkylation Subunits

  摘要：

  The synthesis and preliminary evaluation of 10 and 11, stable precursors to the inherently reactive but isolable p-quinonemethide analog 9 of the CC-1065 and duocarmycin alkylation subunits, are detailed. The p-quinonemethide 9, while reactive (t(1/2) < 1 min, CH3OH), represents one of the few unsubstituted quinonemethides sufficiently stable for isolation and characterization. The structural origin of this stability and the ramifications of the observations on the origin of the stability of the CC-1065 and duocarmycin alkylation subunits are discussed.

  DOI：

  10.1021/jo00096a043

文献信息

• p-Quinonemethide Analog of the CC-1065 and Duocarmycin Alkylation Subunits
  作者：Dale L. Boger、Takahide Nishi、Bradley R. Teegarden

  DOI：10.1021/jo00096a043

  日期：1994.8

  The synthesis and preliminary evaluation of 10 and 11, stable precursors to the inherently reactive but isolable p-quinonemethide analog 9 of the CC-1065 and duocarmycin alkylation subunits, are detailed. The p-quinonemethide 9, while reactive (t(1/2) < 1 min, CH3OH), represents one of the few unsubstituted quinonemethides sufficiently stable for isolation and characterization. The structural origin of this stability and the ramifications of the observations on the origin of the stability of the CC-1065 and duocarmycin alkylation subunits are discussed.