2-(3,4,6,7-tetramethoxyphenanthren-1-yl)ethanol | 1454883-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-(3,4,6,7-tetramethoxyphenanthren-1-yl)ethanol
• 英文别名: 2-(3,4,6,7-Tetramethoxyphenanthren-1-yl)ethanol
• CAS: 1454883-73-8
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: UFRIEZQSMKFKLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4,6,7-tetramethoxyphenanthren-1-yl)ethanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

  摘要：

  Oxa-Pictet Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g] chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.095
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸甲酯 在 sodium tetrahydroborate 、 氢溴酸 、 palladium diacetate 、 potassium carbonate 、 对甲苯磺酸 、 tricyclohexylphosphine tetrafluoroborate 、 calcium chloride 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 140.0 ℃ 、1.38 MPa 条件下， 反应 36.67h， 生成 2-(3,4,6,7-tetramethoxyphenanthren-1-yl)ethanol
  参考文献：
  名称：

  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids

  摘要：

  Oxa-Pictet Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g] chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.095

文献信息

• Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids
  作者：Nirav Kapadia、Wayne Harding

  DOI：10.1016/j.tet.2013.07.095

  日期：2013.10

  Oxa-Pictet Spengler cyclization and microwave-assisted C-H arylation have been implemented as key steps in the synthesis of new isochroman heterocycles containing a 4,5,6a,7-tetrahydrodibenzo[de,g] chromene motif. These isochromans may be easily transformed to phenanthrene alkaloids via acidic cleavage of the isochroman ring and standard synthetic manipulations thereafter. The route described is attractive in that it provides access to two biologically interesting scaffolds in simple and high yielding synthetic steps. (c) 2013 Elsevier Ltd. All rights reserved.