9,10-dihydro-5-hydroxy-3,7-dimethoxy-1,4-phenanthrenedione | 422564-52-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 9,10-dihydro-5-hydroxy-3,7-dimethoxy-1,4-phenanthrenedione
• 英文别名: 5-Hydroxy-3,7-dimethoxy-9,10-dihydrophenanthrene-1,4-dione
• CAS: 422564-52-1
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: RWMAJRUYGIQAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-5-hydroxy-3,7-dimethoxy-1,4-phenanthrenedione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以80%的产率得到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：

  2,4,5-三甲氧基苯甲醛 在 silver(II) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 正丁基锂 、 偶氮二异丁腈 、 碘代三甲硅烷 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 硝酸 、 三正丁基氢锡 、 palladium diacetate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 、 三氟乙酸 、 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 、 乙腈 为溶剂， -78.0~145.0 ℃ 、344.75 kPa 条件下， 反应 43.33h， 生成 9,10-dihydro-5-hydroxy-3,7-dimethoxy-1,4-phenanthrenedione
  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

• Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer
  作者：Shankar Thangaraj、Wen-Shing Tsao、Yi-Wei Luo、Yean-Jang Lee、Chia-Fu Chang、Chun-Cheng Lin、Biing-Jiun Uang、Chia-Chun Yu、Jih-Hwa Guh、Che-Ming Teng

  DOI：10.1016/j.tet.2011.06.054

  日期：2011.8

  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.