2,3,4,7-Tetramethoxy-9-(methoxymethoxy)phenanthrene | 912328-86-0

• 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: 2,3,4,7-Tetramethoxy-9-(methoxymethoxy)phenanthrene
• CAS: 912328-86-0
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: VDXZMQWOMNETOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,7-Tetramethoxy-9-(methoxymethoxy)phenanthrene 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium hydroxide 、 ammonium acetate 、 苄基三乙基氯化铵 、 氢气 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 、 异丙醇 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 N-(1,2,3,9-tetramethoxy-5,6-dihydro-7H-dibenzo[a,c][7]annulen-7-yl)acetamide
  参考文献：
  名称：

  Application of Aryl Siloxane Cross-Coupling to the Synthesis of Allocolchicinoids

  摘要：

  In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O-methyl ether (NCME).

  DOI：

  10.1021/ol061413t
• 作为产物：
  描述：

  2,3,4,7-Tetramethoxy-[9]phenanthrol 、 氯甲基甲基醚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以66%的产率得到2,3,4,7-Tetramethoxy-9-(methoxymethoxy)phenanthrene
  参考文献：
  名称：

  Application of Aryl Siloxane Cross-Coupling to the Synthesis of Allocolchicinoids

  摘要：

  In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O-methyl ether (NCME).

  DOI：

  10.1021/ol061413t

文献信息

• Application of Aryl Siloxane Cross-Coupling to the Synthesis of Allocolchicinoids
  作者：W. Michael Seganish、Philip DeShong

  DOI：10.1021/ol061413t

  日期：2006.8.1

  In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O-methyl ether (NCME).