(+/-)-(E)-methyl 3-(5-(tert-butyldimethylsilyloxy)-2,3,4-trimethoxy-8,9-dihydro-5H-benzocyclohepten-6-yl)acrylate | 1239949-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-(E)-methyl 3-(5-(tert-butyldimethylsilyloxy)-2,3,4-trimethoxy-8,9-dihydro-5H-benzocyclohepten-6-yl)acrylate
• 英文别名: methyl (E)-3-[5-[tert-butyl(dimethyl)silyl]oxy-2,3,4-trimethoxy-8,9-dihydro-5H-benzo[7]annulen-6-yl]prop-2-enoate
• CAS: 1239949-84-8
• 化学式: C₂₄H₃₆O₆Si
• 分子量: 448.632
• InChiKey: YLPGCBIPWKEOEC-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(E)-methyl 3-(5-(tert-butyldimethylsilyloxy)-2,3,4-trimethoxy-8,9-dihydro-5H-benzocyclohepten-6-yl)acrylate 在 silica gel 、 柠檬酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.0h， 以81%的产率得到(+/-)-(E)-methyl 3-(7-hydroxy-1,2,3-trimethoxy-6,7-dihydro-5H-benzocyclohepten-8-yl)acrylate
  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：

  1-(6-But-3-enyl-2,3,4-trimethoxyphenyl)prop-2-ynoxy-tert-butyl-dimethylsilane 、 丙烯酸甲酯（MA） 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到(+/-)-(E)-methyl 3-(5-(tert-butyldimethylsilyloxy)-2,3,4-trimethoxy-8,9-dihydro-5H-benzocyclohepten-6-yl)acrylate
  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