13,14,15-Trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-8-one | 912328-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 13,14,15-Trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-8-one
• 英文别名: 13,14,15-trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-8-one
• CAS: 912328-81-5
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: FDLVXBBMFDIOEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13,14,15-Trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-8-one 在 吡啶 、 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 为溶剂， 生成 N-((11aR)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c][7]annulen-5-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：

  3,4,5-三甲氧基-2-溴苯甲醛 在 palladium on activated charcoal 盐酸 、 palladium diacetate 、 sodium hydroxide 、 三氯化铝 、 氯化亚砜 、 jones reagent 、 四丁基氟化铵 、 苄基三乙基氯化铵 、 氢气 、 sodium acetate 、 sodium hydride 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 、 苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 58.0h， 生成 13,14,15-Trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaen-8-one
  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

• Anti-cancer dibenzocycloheptane derivatives and a catalytic method for dibenzocycloheptane synthesis and allocolchicinoid synthesis
  申请人：University of Windsor

  公开号：EP2952501A2

  公开（公告）日：2015-12-09

  In a non-limiting embodiment, there is provided a compound of formula (I), which may permit for a method or use in treating or preventing a cancer, such as pancreatic cancer or leukemia. In one embodiment, there is also provide a method of preparing a compound of formula (Ia), the method including conducting a cyclization reaction of a compound of formula (III) to obtain a compound of formula (IV), wherein conducting the cyclization reaction comprises conducting a Michael reaction in the presence of a Lewis acid.

  在一种非限制性实施例中，提供了一种式为(I)的化合物，该化合物可能允许用于治疗或预防癌症，如胰腺癌或白血病。在一种实施例中，还提供了一种制备式为(Ia)的化合物的方法，该方法包括通过对式为(III)的化合物进行环化反应以获得式为(IV)的化合物，其中进行环化反应包括在路易斯酸存在下进行Michael反应。
• Catalytic Method for Dibenzocycloheptane Synthesis and Allocolchicinoid Synthesis
  申请人：UNIVERSITY OF WINDSOR

  公开号：US20150344411A1

  公开（公告）日：2015-12-03

  In a non-limiting embodiment, there is provided a compound of formula (I), which may permit for a method or use in treating or preventing a cancer, such as pancreatic cancer or leukemia. In one embodiment, there is also provide a method of preparing a compound of formula (Ia), the method including conducting a cyclization reaction of a compound of formula (III) to obtain a compound of formula (IV), wherein conducting the cyclization reaction comprises conducting a Michael reaction in the presence of a Lewis acid.
• US9573873B2
  申请人：——

  公开号：US9573873B2

  公开（公告）日：2017-02-21
• 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).