10-methyl-9-(1-methylpiperidin-4-yl)-9,10-dihydroacridin-9-ol | 51685-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-methyl-9-(1-methylpiperidin-4-yl)-9,10-dihydroacridin-9-ol
• 英文别名: 10-methyl-9-(1-methyl-piperidin-4-yl)-9,10-dihydro-acridin-9-ol；10-Methyl-9-(1-methylpiperidin-4-yl)acridin-9-ol
• CAS: 51685-15-5
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: XOFBDIMFHUEJHL-UHFFFAOYSA-N

物化性质

• 沸点：
  466.0±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-methyl-9-(1-methylpiperidin-4-yl)-9,10-dihydroacridin-9-ol 在 甲酸 作用下， 反应 20.0h， 以19%的产率得到9,10-dihydro-10-methyl-9-(1-methyl-4-piperidinyl)acridine
  参考文献：
  名称：

  甲酸引起的异常减少

  摘要：

  用回流的甲酸处理of吨甲醇1a或x烯衍生物2a出乎意料地得到二氢化合物3a。当用甲酸处理时，噻吨蒽和a啶甲醇1b和1c以及a啶二烯衍生物2c也被部分还原。

  DOI：

  10.1016/s0040-4039(00)82166-8
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 lithium aluminium tetrahydride 、 sodium hydride 、 sodium sulfate 、 scandium tris(trifluoromethanesulfonate) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 10-methyl-9-(1-methylpiperidin-4-yl)-9,10-dihydroacridin-9-ol
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h

文献信息

• LOUGHHEAD, DAVID G., TETRAHEDRON LETT., 29,(1988) N 45, C. 5701-5702
  作者：LOUGHHEAD, DAVID G.

  DOI：——

  日期：——
• Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of <i>N</i>-Methylacridones
  作者：Xi-An Li、Hong-Li Wang、Shang-Dong Yang

  DOI：10.1021/ol400371h

  日期：2013.4.19

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.
• Unusual reductions induced by formic acid
  作者：David G. Loughhead

  DOI：10.1016/s0040-4039(00)82166-8

  日期：1988.1

  Treatment of xanthene carbinol 1a or xanthenylidene derivative 2a with refluxing formic acid unexpectedly gave dihydro compound 3a. Thioxanthene and acridine carbinols 1b and 1c and acridinylidene derivative 2c were also partially reduced when treated with formic acid.

  用回流的甲酸处理of吨甲醇1a或x烯衍生物2a出乎意料地得到二氢化合物3a。当用甲酸处理时，噻吨蒽和a啶甲醇1b和1c以及a啶二烯衍生物2c也被部分还原。