3-(4-Methoxy-3-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one | 471294-84-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(4-Methoxy-3-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
• 英文别名: 3-(4-methoxy-3-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
• CAS: 471294-84-5
• 化学式: C₂₁H₂₁NO₇
• 分子量: 399.4
• InChiKey: JEUHHEQSMOKGDH-UHFFFAOYSA-N

物化性质

• 沸点：
  543.8±50.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxy-3-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one 在 溶剂黄146 、 锌 作用下， 反应 3.0h， 以78%的产率得到3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylacetyl chloride 在 吡啶 、 TEA 、 硫酸 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.5h， 生成 3-(4-Methoxy-3-nitrophenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9