2,3,4-trimethoxy-9-phenanthrol | 912328-77-9

• 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-trimethoxy-9-phenanthrol
• 英文别名: 2,3,4-Trimethoxyphenanthren-9-ol；2,3,4-trimethoxyphenanthren-9-ol
• CAS: 912328-77-9
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: DNHYCBDJXXQHMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethoxy-9-phenanthrol 在 sodium hydroxide 、 苄基三乙基氯化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1,1-dichloro-1a,9b-dihydro-6,7,8-trimethoxy-1a-(methoxymethoxy)-1H-cyclopropa[l]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
• 作为产物：
  描述：

  3,4,5-三甲氧基-2-溴苯甲醛 在 盐酸 、 palladium diacetate 、 三氯化铝 、 氯化亚砜 、 jones reagent 、 四丁基氟化铵 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 、 苯 为溶剂， 反应 34.0h， 生成 2,3,4-trimethoxy-9-phenanthrol
  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).