1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene | 183730-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene
• 英文别名: 1-(2,2-Dibromoethenyl)-2,4,5-trimethoxybenzene
• CAS: 183730-32-7
• 化学式: C₁₁H₁₂Br₂O₃
• 分子量: 352.022
• InChiKey: SYKHYYCHAJXNEF-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  392.8±37.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene 在 silver(II) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 碘代三甲硅烷 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 硝酸 、 palladium diacetate 、 三乙胺 、 N,N-二甲基甲酰胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~145.0 ℃ 、344.75 kPa 条件下， 反应 38.83h， 生成 5-hydroxy-3,7-dimethoxy-1,4-phenanthraquinone, denbinobin
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054
• 作为产物：
  描述：

  四溴化碳 、 2,4,5-三甲氧基苯甲醛 在 三苯基膦 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 以93%的产率得到1,1-dibromo-2-(2,4,5-trimethoxyphenyl)ethene
  参考文献：
  名称：

  Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer

  摘要：

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.054

文献信息

• Synthesis of a magnosalin derivative, 4-(3,4,5-trimethoxyphenyl)-6-(2,4,5-trimethoxyphenyl)-2-diethylaminopyrimidine, and the anti-angiogenic and anti-rheumatic effect on mice by oral administration
  作者：Katsunao Tanaka、Yasuo Konno、Yasushi Kuraishi、Ikuko Kimura、Takashi Suzuki、Mamoru Kiniwa

  DOI：10.1016/s0960-894x(01)00810-1

  日期：2002.2

  We describe here the synthesis and the anti-angiogenic and anti-rheumatic activities of 4-(3,4,5-trimethoxyphenyl)-6-(2,4,5-trimethoxyphenyl)-2-diethylaminopyrimidine (TAS-202), a derivative of magnosalin, which is a natural product isolated from Flos magnoliae. TAS-202 inhibited the proliferation of vascular endothelial cells more potently than magnosalin, and when given orally it inhibited basic fibroblast growth factor (bFGF)-induced angiogenesis and collagen-induced arthritis in mice. This magnosalin derivative with anti-angiogenic effects is a candidate for the treatment of rheumatoid arthritis. (C) 2002 Elsevier Science Ltd. All rights reserved.