9,10,11-trimethoxy-5-methyl-7H-dibenzo[a,c]cycloheptene-2-carboxylic acid methyl ester | 1239949-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 9,10,11-trimethoxy-5-methyl-7H-dibenzo[a,c]cycloheptene-2-carboxylic acid methyl ester
• CAS: 1239949-97-3
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: QOKKHKLYRMNSEG-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  9,10,11-trimethoxy-5-methyl-7H-dibenzo[a,c]cycloheptene-2-carboxylic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以77%的产率得到(+/-)-9,10,11-trimethoxy-5-methyl-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-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
• 作为产物：
  描述：

  (+/-)-5-hydroxy-9,10,11-trimethoxy-5-methyl-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2-carboxylic acid methyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到9,10,11-trimethoxy-5-methyl-7H-dibenzo[a,c]cycloheptene-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