1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetylene | 1010733-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetylene
• 英文别名: 5-(3,4-Dimethoxy-phenylethynyl)-1,2,3-trimethoxy-benzene；5-[2-(3,4-dimethoxyphenyl)ethynyl]-1,2,3-trimethoxybenzene
• CAS: 1010733-56-8
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: FCFKFKWVYFJVGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetylene 在 potassium permanganate 、 四氯化钛 、 碳酸氢钠 、 magnesium sulfate 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.09h， 生成 2,3,4,6,7-pentamethoxy-9,10-phenanthrenequinone
  参考文献：
  名称：

  Synthesis of Highly Functionalized 9,10-Phenanthrenequinones by Oxidative Coupling Using MoCl₅

  摘要：

  The strong oxidative power of molybdenum pentachloride gives rise to an efficient oxidative C-C bond formation of benzil derivatives to the corresponding 9,10-phenanthrenequinones. A highly complementary method to previous approaches was developed. The required derivatives are accessible in a modular fashion and in excellent yields. By this approach the orchid-derived natural product cypripediquinone A was synthesized for the first time.

  DOI：

  10.1021/ol300948u
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 、 3,4-二甲氧基苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以73%的产率得到1-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acetylene
  参考文献：
  名称：

  Synthesis of Highly Functionalized 9,10-Phenanthrenequinones by Oxidative Coupling Using MoCl₅

  摘要：

  The strong oxidative power of molybdenum pentachloride gives rise to an efficient oxidative C-C bond formation of benzil derivatives to the corresponding 9,10-phenanthrenequinones. A highly complementary method to previous approaches was developed. The required derivatives are accessible in a modular fashion and in excellent yields. By this approach the orchid-derived natural product cypripediquinone A was synthesized for the first time.

  DOI：

  10.1021/ol300948u

文献信息

• One-pot hydrosilylation–protodesilylation of functionalized diarylalkynes: a highly selective access to Z-stilbenes. Application to the synthesis of combretastatin A-4
  作者：Anne Giraud、Olivier Provot、Abdallah Hamzé、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.tetlet.2007.12.057

  日期：2008.2

  An efficient stereoselective synthesis of Z-stilbenes has been developed from diarylalkynes via a new hydrosilylation-protodesilylation process. The scope and limitation of this method is presented to stereo selectively prepare a wide range of (Z)-stilbenes in a one-pot way is presented. A concise application to the preparation of combretastatin A-4 (CA-4), a vascular targeting agent inhibitor of tubulin polymerisation is described. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and antitumor activity of benzils related to combretastatin A-4
  作者：Céline Mousset、Anne Giraud、Olivier Provot、Abdallah Hamze、Jérôme Bignon、Jian-Miao Liu、Sylviane Thoret、Joëlle Dubois、Jean-Daniel Brion、Mouâd Alami

  DOI：10.1016/j.bmcl.2008.04.053

  日期：2008.6

  A series of benzil derivatives related to combretastatin A-4 (CA-4) have been synthesized by oxidation of diarylalkynes promoted by PdI2 in DMSO. Using this new protocol, 14 benzils were prepared in good to excellent yields and their biological activity has been delineated. Several benzils exhibited excellent antiproliferative activity: for example, 4j and 4k bearing the greatest resemblance to CA-4 and AVE-8062, respectively, were found to inhibit cell growth at the nanomolar level (20-50 nM) on four human tumor cell lines. Flow cytometric analysis indicates that these compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. A cell-based assay indicated that compounds 4j and 4k displayed a similar inhibition of tubulin assembly with an IC50 value similar to CA-4. These results clearly demonstrated that the Z-double bond of CA-4 can be replaced by a 1,2-diketone unit without significant loss of cytotoxicity and inhibition of tubulin assembly potency. (C) 2008 Elsevier Ltd. All rights reserved.