(+/-)-5-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2,3-dicarboxylic acid dimethyl ester | 1239949-88-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: (+/-)-5-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2,3-dicarboxylic acid dimethyl ester
• CAS: 1239949-88-2
• 化学式: C₂₂H₂₄O₈
• 分子量: 416.428
• InChiKey: HRDNMTIKVTZKFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (+/-)-5-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2,3-dicarboxylic acid dimethyl ester 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89%的产率得到(+/-)-5-fluoro-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2,3-dicarboxylic acid dimethyl 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：

  dimethyl 9,10,11-trimethoxy-1-nitro-5-oxo-2,3,5,6,7,11b-hexahydro-1H-dibenzo[a,c][7]annulene-2,3-dicarboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以16 mg的产率得到9,10,11-trimethoxy-5-oxo-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2,3-dicarboxylic acid dimethyl 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