(E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide | 120743-62-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: (E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide
• CAS: 120743-62-6
• 化学式: C₅₉H₇₇NO₁₃Si₂
• 分子量: 1064.43
• InChiKey: FTRIWAZDVJZBOU-SUJRHVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.15
• 重原子数：
  75.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  207.38
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide 在 甲醇 、 potassium fluoride 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(E)-5,6-Bis-(4-hydroxy-phenyl)-oct-5-enoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide
  参考文献：
  名称：

  Diethylstilbestrol-linked cytotoxic agents. Synthesis and binding affinity for estrogen receptors

  摘要：

  The syntheses of diethylstilbestrol derivatives with a C4 side chain at the double bond bearing various functional and potentially alkylating groups (9-25, 38-40, 43, 44) as well as the coupling product with daunorubicin (41) are described. Derivatives with free phenolic groups show easy isomerization to (Z)-stilbenes and styrenes, which could be minimized with silyl protecting groups. Estrogen receptor binding is decreased by polar groups such as carboxylic acids (10) as well as sterically demanding substituents.

  DOI：

  10.1021/jm00127a022
• 作为产物：
  描述：

  5,6-bis<4-(tert-butyldimethylsiloxy)phenyl>-5-octenoic acid 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (E)-5,6-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-oct-5-enoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide
  参考文献：
  名称：

  Diethylstilbestrol-linked cytotoxic agents. Synthesis and binding affinity for estrogen receptors

  摘要：

  The syntheses of diethylstilbestrol derivatives with a C4 side chain at the double bond bearing various functional and potentially alkylating groups (9-25, 38-40, 43, 44) as well as the coupling product with daunorubicin (41) are described. Derivatives with free phenolic groups show easy isomerization to (Z)-stilbenes and styrenes, which could be minimized with silyl protecting groups. Estrogen receptor binding is decreased by polar groups such as carboxylic acids (10) as well as sterically demanding substituents.

  DOI：

  10.1021/jm00127a022