(+/-)-5-fluoro-9,10,11-trimethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctadiene-2-carboxylic acid methyl ester | 1239950-01-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (+/-)-5-fluoro-9,10,11-trimethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctadiene-2-carboxylic acid methyl ester
• CAS: 1239950-01-6
• 化学式: C₂₁H₂₃FO₅
• 分子量: 374.409
• InChiKey: OKZGFMYDIUHFJO-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  Methyl 8-hydroxy-14,15,16-trimethoxytricyclo[10.4.0.02,7]hexadeca-1(16),2(7),3,5,12,14-hexaene-4-carboxylate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83%的产率得到(+/-)-5-fluoro-9,10,11-trimethoxy-5,6,7,8-tetrahydro-dibenzo[a,c]cyclooctadiene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of new allocolchicinoids

  摘要：

  Allocolchicinoids with B- and C-ring variations were synthesized using sequential enyne-metathesis/Diets-Alder reactions (A -> AB -> ABC approach) and evaluated for their inhibitory effect on tubulin assembly in vitro. (-)-Allocolchicine 11 with methyl ester at C10 and (+/-)-cyclopropyl allocolchicinoid 32 exhibit similar activity than (-)-colchicine (1), probably derived from a similar flexibility in the biphenyl system. The presence of methyl ester at C10 led to a little loss in potency in comparison with the series with methyl ester at C9. A complete loss of activity was observed for allocolchicine 9 with methyl ester at C11. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2010.03.003