1,2-bis(4-benzyloxy-3-methoxyphenyl)-1-ethanone | 3122-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(4-benzyloxy-3-methoxyphenyl)-1-ethanone
• 英文别名: 4,4'-dibenzyloxy-3,3'-dimethoxy-deoxybenzoin；4,4'-Dibenzyloxy-3,3'-dimethoxy-desoxybenzoin；1,2-bis(3-methoxy-4-phenylmethoxyphenyl)ethanone
• CAS: 3122-36-9
• 化学式: C₃₀H₂₈O₅
• 分子量: 468.549
• InChiKey: RUZRAOMDNPWNAG-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  628.0±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,2-双(4-羟基-3-甲氧基苯基)乙酮 、 氯化苄 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以3.5 g的产率得到1,2-bis(4-benzyloxy-3-methoxyphenyl)-1-ethanone
  参考文献：
  名称：

  Berndtsson, Ingmar; Khanna, Bhushan L.; Lundquist, Knut, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 6, p. 453 - 455

  摘要：

  DOI：

文献信息

• STUDIES IN THE POLYOXYPHENOL SERIES: IX. THE SYNTHESIS OF PAPAVERINE AND PAPAVERALDINE BY THE POMERANZ-FRITSCH METHOD
  作者：Donald A. Guthrie、Arlen W. Frank、C. B. Purves

  DOI：10.1139/v55-090

  日期：1955.5.1

  Fritsch's cyclization of N-(α-veratrylveratrylidene)-aminoacetal in sulphuric acid was shown to give 1.1% of papaverine and 23% of an isomer, m.p. 164.5–165.5 °C.; hydrochloride, m.p. 212 °C. decomp., which was supposed to be 4,5-bis(3,4-dimethoxyphenyl)-2H-pyrrolenine, produced by an internal condensation of the acetal or the corresponding aldehyde with the reactive methylene group. A similar structure was proposed for another unidentified isomer prepared by Schlittler and Müller. Hydrogenation of Fritsch's acetal gave N-(α-veratryl-veratryl)-aminoacetal, m.p. 69.5–70 °C., which was cyclized to a base, m.p. 155.5–156 °C.; N-acetyl derivative, m.p. 203.5–204 °C., formulated as 2,3-bis(3,4-dimethoxyphenyl)-3-pyrroline. Substances presumed to be the intermediate aldehyde and aldol were isolated as colorless oils. Condensation of the diketone veratril with aminoacetal, followed by cyclization of the crude product, constituted a new two-step synthesis of papaveraldine in 8% yield, and the reduction of the latter to papaverine was known.Other crystalline compounds prepared incidentally and thought to be new were veratril monoanil, m.p. 172–173 °C.; α,α′-biveratrylideneaminoacetal, m.p. 101–102 °C.; a compound formulated as 2,3-bis(3,4-dimethoxyphenyl)-4-ethylmer-captopyrrolidine hydrochloride, m.p. 184–185 °C; from this an unidentified mercury complex, m.p. 109 °C. decomp.; 4,4′dibenzyloxy-3,3′-dimethoxy-desoxybenzoin, m.p. 141–142 °C; and its oxime, m.p. 137.5 °C.

  Fritsch在硫酸中对N-(α-芍药碱基芍药碱亚甲基)-氨基乙醛进行环化反应，结果显示产率为1.1%的罂粟碱和23%的异构体，熔点为164.5–165.5°C；盐酸盐，熔点为212°C分解。这种异构体被认为是4,5-双(3,4-二甲氧基苯基)-2H-吡咯烯，通过乙醛或相应醛与活性甲基的内部缩合产生。 Schlittler和Müller制备的另一种未知异构体也提出了类似的结构。Fritsch的亚甲基环化反应产生了N-(α-芍药碱基芍药碱)-氨基乙醛，熔点为69.5–70°C，它被环化成一种碱，熔点为155.5–156°C；N-乙酰衍生物，熔点为203.5–204°C，被确定为2,3-双(3,4-二甲氧基苯基)-3-吡咯烯。假定为中间醛和醛缩合物的物质被分离为无色油状物。芍药碱的新的两步合成方法包括芍药碱基芍药碱与氨基乙醛的缩合，随后对粗产品进行环化反应，产率为8%。将后者还原为罂粟碱是已知的。其他结晶化合物包括芍药碱基单苯胺，熔点为172–173°C；α,α′-双(芍药碱基)-氨基乙醛，熔点为101–102°C；一种被确定为2,3-双(3,4-二甲氧基苯基)-4-乙基巯基吡咯啉盐酸盐的化合物，熔点为184–185°C；从中得到的未知汞络合物，熔点为109°C分解；4,4′-二苄氧基-3,3′-二甲氧基-去氧苯酮，熔点为141–142°C；以及它的肟，熔点为137.5°C。