7-methoxy-1-(piperidin-1-yl)-9,10-dihydrophenanthrene-2-carbonitrile

• 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: 7-methoxy-1-(piperidin-1-yl)-9,10-dihydrophenanthrene-2-carbonitrile
• 英文别名: 7-Methoxy-1-piperidin-1-yl-9,10-dihydrophenanthrene-2-carbonitrile；7-methoxy-1-piperidin-1-yl-9,10-dihydrophenanthrene-2-carbonitrile
• 化学式: C₂₁H₂₂N₂O
• 分子量: 318.418
• InChiKey: XLLGVLAIOGRCHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,6-dihydro-8-methoxy-4-methylsulfanyl-2-oxo-2H-benzo[h]chromene-3-carbonitrile 在 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-methoxy-1-(piperidin-1-yl)-9,10-dihydrophenanthrene-2-carbonitrile
  参考文献：
  名称：

  Acetyltrimethylsilane mediated synthesis of dihydrophenanthrenes

  摘要：

  An easy and efficient synthesis of phenanthrene derivatives through base catalyzed ring transformation of 4-sec-amino-2oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrites with acetyltrimethylsilane is described in good yields. The advantage of this reaction is the direct transformation of 2-oxobenzo[h]chromene into phenanthrene via C-C insertion from acetyltrimethylsilane. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.014

文献信息

• Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes
  作者：Pratik Yadav、Ranjay Shaw、Amr Elagamy、Abhinav Kumar、Ramendra Pratap

  DOI：10.1039/c8ob01270a

  日期：——

  functionalized 2H-pyran-2-ones has been demonstrated for the synthesis of various multi-substituted benzenes through a tandem process. We observed that lithium hydroxide provides a major product from α-attack and a minor product from γ-attack of allyl cyanide, while the use of sodium hydride as a base exclusively provides the product by γ-attack of allyl cyanide. We have also performed NMR experiments to understand

  已经证明了适当官能化的2 H-吡喃-2-酮的碱控制的区域选择性1，6-氰基烯丙基化用于通过串联方法合成各种多取代的苯。我们观察到，氢氧化锂提供的主要产物是α-攻击，而次要的产物是γ-烯丙基氰，而氢化钠作为碱只能提供γ-攻击的烯丙基氰。我们还进行了NMR实验，以了解机理。该化合物的结构通过单晶X射线分析确认。
• Acetyltrimethylsilane mediated synthesis of dihydrophenanthrenes
  作者：Ramendra Pratap、Vishnu Ji Ram

  DOI：10.1016/j.tetlet.2007.07.014

  日期：2007.9

  An easy and efficient synthesis of phenanthrene derivatives through base catalyzed ring transformation of 4-sec-amino-2oxo-5,6-dihydro-2H-benzo[h]chromene-3-carbonitrites with acetyltrimethylsilane is described in good yields. The advantage of this reaction is the direct transformation of 2-oxobenzo[h]chromene into phenanthrene via C-C insertion from acetyltrimethylsilane. (c) 2007 Elsevier Ltd. All rights reserved.