2-methoxy-5-((3,4,5-trimethoxyphenyl)ethynyl)phenyl acetate | 1042149-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-methoxy-5-((3,4,5-trimethoxyphenyl)ethynyl)phenyl acetate
• CAS: 1042149-59-6
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: CIJOFWFPQBTPAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-((3,4,5-trimethoxyphenyl)ethynyl)phenyl acetate 在 二甲基亚砜 、 palladium(II) iodide 作用下， 反应 3.0h， 以85%的产率得到[2-Methoxy-5-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]phenyl] acetate
  参考文献：
  名称：

  Synthesis and antitumor activity of benzils related to combretastatin A-4

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.04.053
• 作为产物：
  描述：

  5-碘-1,2,3-三甲氧基苯 在 四氢吡咯 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-methoxy-5-((3,4,5-trimethoxyphenyl)ethynyl)phenyl acetate
  参考文献：
  名称：

  Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

  摘要：

  We herein describe a B(2)Pin(2)-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.

  DOI：

  10.1021/acs.joc.9b00321