5-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one | 939824-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one
• CAS: 939824-70-1
• 化学式: C₃₃H₃₆O₉
• 分子量: 576.643
• InChiKey: RVPVPOIUKWQKDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以68%的产率得到5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one
  参考文献：
  名称：

  The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  摘要：

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.006
• 作为产物：
  描述：

  3-异丙基-4-甲氧基苯甲醛 在 palladium diacetate 正丁基锂 、 四丁基氯化铵 、 sodium acetate 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-isopropoxy-2-(3-isopropoxy-4-methoxyphenyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one
  参考文献：
  名称：

  The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  摘要：

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.006