Methyl 13,14,15-trimethoxy-8-oxotricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaene-4-carboxylate | 934749-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 13,14,15-trimethoxy-8-oxotricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaene-4-carboxylate
• CAS: 934749-84-5
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: WGAQJFNJHHXTBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 13,14,15-trimethoxy-8-oxotricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaene-4-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 methyl 8-hydroxy-13,14,15-trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaene-4-carboxylate
  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：

  methyl 3-(3,4,5-trimethoxyphenyl)propionate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 咪唑 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 四丁基氟化铵 、 silica gel 、 四氯化锡 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 336110.0h， 生成 Methyl 13,14,15-trimethoxy-8-oxotricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,11,13-hexaene-4-carboxylate
  参考文献：
  名称：

  使用顺序的闭环烯炔复分解-Diels-Alder反应合成花环酚。

  摘要：

  已使用烯键闭环复分解（RCM）反应合成七元环和Diels-Alder-芳香化序列来合成芳香环，合成了在C10或C11位置的C环中具有官能团的新金属酚类化合物C. [反应：见正文]。

  DOI：

  10.1021/ol0630548

文献信息

• Synthesis of New Allocolchicinoids with Seven- and Eight-Membered B-Rings by Enyne Ring-Closing Metathesis
  作者：François-Didier Boyer、Issam Hanna

  DOI：10.1002/ejoc.200800595

  日期：2008.10

  functionality in the C-ring at the C10 or C11 positions, is reported. An asymmetric synthesis of (7S)-allocolchicine 5 is also described. The main features included the elaboration of a common intermediate, the AB bicyclic ring system, in which the construction of the seven-membered ring was achieved by an enyne ring-closing metathesis (RCM) reaction. A subsequent Diels–Alder/aromatization sequence afforded the

  报告了别秋水仙碱 4 和 5 的全合成，在 C 环中的 C10 或 C11 位置具有酯官能团。还描述了 (7S)-allocolchicine 5 的不对称合成。主要特征包括对常见中间体 AB 双环系统的阐述，其中七元环的构建是通过烯炔闭环复分解 (RCM) 反应实现的。随后的 Diels-Alder/芳构化序列提供了一组具有高区域选择性的官能化环 C 别秋水仙素。该策略也用于合成含有八元 B 环的别秋水仙碱 6。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• Synthesis of Allocolchicines Using Sequential Ring-Closing Enyne Metathesis−Diels−Alder Reactions
  作者：François-Didier Boyer、Issam Hanna

  DOI：10.1021/ol0630548

  日期：2007.2.1

  New allocolchinoids having functionality in the C ring at position C10 or C11 have been synthesized using the enyne ring-closing metathesis (RCM) reaction for construction of the seven-membered ring and a Diels-Alder-aromatization sequence for the elaboration of the aromatic ring C. [reaction: see text].

  已使用烯键闭环复分解（RCM）反应合成七元环和Diels-Alder-芳香化序列来合成芳香环，合成了在C10或C11位置的C环中具有官能团的新金属酚类化合物C. [反应：见正文]。
• Synthesis and tubulin-binding properties of new allocolchicinoids
  作者：François-Didier Boyer、Joëlle Dubois、Sylviane Thoret、Marie-Elise Tran Huu Dau、Issam Hanna

  DOI：10.1016/j.bioorg.2010.03.003

  日期：2010.8

  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.