1-phenyl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione | 109248-36-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-phenyl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
• 英文别名: benzil；3,4,5-Trimethoxy-benzil
• CAS: 109248-36-4
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: RVWFWQXFUXJPID-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione 、 环己酮 在 ammonium acetate 作用下， 反应 4.0h， 以74%的产率得到2-phenyl-3-(3,4,5-trimethoxyphenyl)-1,4-diazaspiro[4.5]deca-1,3-diene
  参考文献：
  名称：

  从二取代炔烃合成 1,2,4,5-四取代-2 H-咪唑的顺序一锅法†

  摘要：

  已经从双取代炔烃和结构上不同的酮开发了一种对四取代的2 H-咪唑支架的顺序一锅法。反应通过内部炔烃生成的二酮中间体进行，然后加入乙酸铵和合适的酮，从而提供各种2 H-咪唑。使用空气湿度稳定的反应条件和廉价的试剂，该转化证明了广泛的底物范围和良好的官能团相容性。

  DOI：

  10.1039/c5nj00959f
• 作为产物：
  描述：

  1,2,3-trimethoxy-5-(phenylethynyl)benzene 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 1-phenyl-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
  参考文献：
  名称：

  从二取代炔烃合成 1,2,4,5-四取代-2 H-咪唑的顺序一锅法†

  摘要：

  已经从双取代炔烃和结构上不同的酮开发了一种对四取代的2 H-咪唑支架的顺序一锅法。反应通过内部炔烃生成的二酮中间体进行，然后加入乙酸铵和合适的酮，从而提供各种2 H-咪唑。使用空气湿度稳定的反应条件和廉价的试剂，该转化证明了广泛的底物范围和良好的官能团相容性。

  DOI：

  10.1039/c5nj00959f

文献信息

• Mild Mn(OAc)₃-Mediated Aerobic Oxidative Decarboxylative Coupling of Arylboronic Acids and Arylpropiolic Acids: Direct Access to Diaryl 1,2-Diketones
  作者：Wen-Xin Lv、Yao-Fu Zeng、Shang-Shi Zhang、Qingjiang Li、Honggen Wang

  DOI：10.1021/acs.orglett.5b01265

  日期：2015.6.19

  A simple and efficient method for the synthesis of diaryl 1,2-diketones has been developed. The reaction represents the first example of diaryl 1,2-diketones that are synthesized directly from arylboronic acids and arylpropiolic acids by a radical pathway in moderate to good yields. This reaction proceeds under mild reaction conditions and with good tolerance of a variety of functional groups. Preliminary

  已经开发了一种简单有效的合成二芳基1,2-二酮的方法。该反应代表二芳基1,2-二酮的第一个实例，该二芳基1,2-二酮是通过自由基途径由芳基硼酸和芳基丙酸直接合成的，产率中等至良好。该反应在温和的反应条件下进行，并且对各种官能团具有良好的耐受性。进行了初步的力学研究。
• Microwave-assisted efficient synthesis of 1,2-diaryldiketones: a novel oxidation reaction of diarylalkynes with DMSO promoted by FeBr3
  作者：Anne Giraud、Olivier Provot、Jean-François Peyrat、Mouâd Alami、Jean-Daniel Brion

  DOI：10.1016/j.tet.2006.05.072

  日期：2006.8

  This paper reports the oxidation of functionalized diarylalkynes with DMSO in the presence of the environmentally friendly FeBr3 catalyst. This non-toxic procedure is general and has been applied successfully under microwave irradiation leading rapidly to benzil derivatives in good yields.

  本文报道了在环保型FeBr 3催化剂存在下用DMSO氧化官能化的二芳基炔烃。这种无毒方法是通用的，已成功地在微波辐射下应用，可迅速以良好的收率生产出苯并衍生物。
• 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.