3-(3,3-二乙氧基丙-1-炔基)-1,4-二甲氧基萘-2-甲醛 | 1286188-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(3,3-二乙氧基丙-1-炔基)-1,4-二甲氧基萘-2-甲醛
• 英文名称: 3-(3,3-diethoxyprop-1-ynyl)-1,4-dimethoxynaphthalene-2-carbaldehyde
• 英文别名: 3-(3,3-Diethoxyprop-1-ynyl)-1,4-dimethoxynaphthalene-2-carbaldehyde
• CAS: 1286188-41-7
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: KUATYQGPXMYJLO-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙醛二乙基乙缩醛 、 3-bromo-1,4-dimethoxy-2-naphthaldehyde 在 copper(l) iodide 、 三叔丁基膦 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以31%的产率得到3-(3,3-二乙氧基丙-1-炔基)-1,4-二甲氧基萘-2-甲醛
  参考文献：
  名称：

  Synthesis of 3-substituted benzo[g]isoquinoline-5,10-diones: a convenient one-pot Sonogashira coupling/iminoannulation procedure

  摘要：

  A series of 3-substituted 5,10-dimethoxybenzo[g]isoquinolines were prepared by coupling of terminal alkynes with the tert-butylimine of 3-bromo-1,4-dimethoxy-2-naphthaldehyde in the presence of a Pd-catalyst and subsequent Cu-catalyzed cyclization of the intermediate 3-alkynyl-2-naphthylcarbaldehyde. A CAN-mediated oxidative demethylation yielded the corresponding 2-azaanthraquinones in excellent yields. Since this methodology proved to be limited to alkynes bearing aromatic groups, an alternative and more general Pd-catalyzed coupling procedure was developed, starting from 3-bromo-1,4-dimethoxy-2-naphthaldehyde. For more acidic terminal alkynes, like phenylacetylene, a combination of Pd(OAc)(2)/P(t-Bu)(3)/CuI (2/6/1) with potassium carbonate in DMF gave a complete conversion within 24 h. For less acidic acetylenes, 2 equiv of alkyne and caesium carbonate as a base were required in order to obtain complete conversion of the starting material within 24 h. These altered Sonogashira conditions also allowed the isolation of a benzo[f]indenone as an interesting side product in case Bu4NCl was added to the reaction mixture. The 3-allcynyl-1,4-dimethoxy-2-naphthaldehyde acquired after completion of the Pd-catalyzed coupling could be cyclized by adding a solution of ethanolic ammonia and an extra equivalent of potassium carbonate to the reaction mixture. As such, this consecutive one-pot coupling/iminoannulation procedure was a convenient alternative to the Larock isoquinoline procedure, enabling the isolation of a series of 3-substituted 5,10-dimethoxybenzo[g]isoquinolines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.074

文献信息

• Synthesis of 3-substituted benzo[g]isoquinoline-5,10-diones: a convenient one-pot Sonogashira coupling/iminoannulation procedure
  作者：Sam Van Aeken、Stefan Verbeeck、Jurgen Deblander、Bert U.W. Maes、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2011.01.074

  日期：2011.3

  A series of 3-substituted 5,10-dimethoxybenzo[g]isoquinolines were prepared by coupling of terminal alkynes with the tert-butylimine of 3-bromo-1,4-dimethoxy-2-naphthaldehyde in the presence of a Pd-catalyst and subsequent Cu-catalyzed cyclization of the intermediate 3-alkynyl-2-naphthylcarbaldehyde. A CAN-mediated oxidative demethylation yielded the corresponding 2-azaanthraquinones in excellent yields. Since this methodology proved to be limited to alkynes bearing aromatic groups, an alternative and more general Pd-catalyzed coupling procedure was developed, starting from 3-bromo-1,4-dimethoxy-2-naphthaldehyde. For more acidic terminal alkynes, like phenylacetylene, a combination of Pd(OAc)(2)/P(t-Bu)(3)/CuI (2/6/1) with potassium carbonate in DMF gave a complete conversion within 24 h. For less acidic acetylenes, 2 equiv of alkyne and caesium carbonate as a base were required in order to obtain complete conversion of the starting material within 24 h. These altered Sonogashira conditions also allowed the isolation of a benzo[f]indenone as an interesting side product in case Bu4NCl was added to the reaction mixture. The 3-allcynyl-1,4-dimethoxy-2-naphthaldehyde acquired after completion of the Pd-catalyzed coupling could be cyclized by adding a solution of ethanolic ammonia and an extra equivalent of potassium carbonate to the reaction mixture. As such, this consecutive one-pot coupling/iminoannulation procedure was a convenient alternative to the Larock isoquinoline procedure, enabling the isolation of a series of 3-substituted 5,10-dimethoxybenzo[g]isoquinolines. (C) 2011 Elsevier Ltd. All rights reserved.