<5,6>benzo-1,4-dimethoxy-7,8-dihydroacridine | 146830-15-1

• 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: <5,6>benzo-1,4-dimethoxy-7,8-dihydroacridine
• 英文别名: 8,11-dimethoxy-5,6-dihydrobenz[c]acridine；8,11-Dimethoxy-5,6-dihydrobenzo[c]acridine
• CAS: 146830-15-1
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: NZRKXRHZPFSDLL-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±40.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <5,6>benzo-1,4-dimethoxy-7,8-dihydroacridine 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以72%的产率得到<5,6>benzo-7,8-dihydroacridine-1,4-dione
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012
• 作为产物：
  描述：

  2-萘甲醛,1-溴-3,4-二氢- 在 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 13.0h， 生成 <5,6>benzo-1,4-dimethoxy-7,8-dihydroacridine
  参考文献：
  名称：

  Chemoselective arylamination of β-bromovinylaldehydes followed by acid catalyzed cyclization: a general method for polycyclic quinolines

  摘要：

  A synthesis of polycyclic quinolines is described via palladium-catalyzed chemoselective arylamination of beta-bromovinylaldehydes with aromatic amines followed by acid catalyzed cyclization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.111

文献信息

• Synthesis of 5,6-dihydrobenz[c]acridines: a comparative study
  作者：P. Karthikeyan、A. Meena Rani、R. Saiganesh、K.K. Balasubramanian、S. Kabilan

  DOI：10.1016/j.tet.2008.11.049

  日期：2009.1

  5,6-Dihydrobenz[c]acridines were synthesized by the reaction of 1-chloro-3,4-dihydro-2-naphthaldehyde with aromatic amines under three different conditions: a. Thermolysis of 1-chlorovinyl-(N-aryl)imines prepared from 1-chloro-3,4-dihydro-2-naphthaldehyde. b. Acid catalyzed cyclization of 1-(N-aryl)amino-3,4-dihydro-2-naphthaldehydes. c. Thermolysis of N-arylenaminoimine hydrochlorides derived from

  通过1-氯-3,4-二氢-2-萘醛与芳族胺在三种不同条件下的反应合成5,6-二氢苯并[ c ] ac啶： 一种。 由1-氯-3，4-二氢-2-萘醛制备的1-氯乙烯基- （N-芳基）亚胺的热解。 b。 1-（N-芳基）氨基-3,4-二氢-2-萘醛的酸催化环化反应。 C。 在DMF介质中热解1-氯-3,4-二氢-2-萘醛衍生的N-芳基氨基亚胺盐酸盐。所有这三种方法仅产生5,6-二氢苯并[ c ] ac啶，而没有异构体7,8-二氢苯并[ k ]菲啶。 通过详细的NMR光谱研究，独立的合成以及单晶XRD研究已明确确定了这些产物的结构。
• Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities
  作者：Randolph P. Thummel、Sara Chirayil、Christophe Hery、Jean Luc Lim、Tie Lin Wang

  DOI：10.1021/jo00059a012

  日期：1993.3

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.
• Chemoselective arylamination of β-bromovinylaldehydes followed by acid catalyzed cyclization: a general method for polycyclic quinolines
  作者：Surajit Some、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2007.05.111

  日期：2007.7

  A synthesis of polycyclic quinolines is described via palladium-catalyzed chemoselective arylamination of beta-bromovinylaldehydes with aromatic amines followed by acid catalyzed cyclization. (C) 2007 Elsevier Ltd. All rights reserved.