2-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethanone | 931407-29-3

• 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: 2-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethanone
• CAS: 931407-29-3
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: BIYUVRRREAWACB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethanone 在 氯化亚砜 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 7.0h， 生成 5-(4-Nitro-phenyl)-4-(3,4,5-trimethoxy-phenyl)-[1,2,3]thiadiazole
  参考文献：
  名称：

  Synthesis and activity of Combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents

  摘要：

  A series of 4,5-disubstitute-1,2,3-thiadiazole compounds were designed and synthesized as potent anticancer agents, some of them exhibited excellent in vitro and in vivo inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.060
• 作为产物：
  描述：

  [(Tetrahydro-pyran-2-yloxy)-(3,4,5-trimethoxy-phenyl)-methyl]-phosphonic acid dimethyl ester 在 盐酸 、 potassium tert-butylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 19.0h， 生成 2-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and activity of Combretastatin A-4 analogues: 1,2,3-thiadiazoles as potent antitumor agents

  摘要：

  A series of 4,5-disubstitute-1,2,3-thiadiazole compounds were designed and synthesized as potent anticancer agents, some of them exhibited excellent in vitro and in vivo inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.060

文献信息

• Design, synthesis and biological evaluation of 3,4-diaryl-1,2,5-oxadiazole-2/5-oxides as highly potent inhibitors of tubulin polymerization
  作者：Yilang Hong、Yinglin Zhao、Lei Yang、Minghuan Gao、Long Li、Shuai Man、Zhan Wang、Qi Guan、Kai Bao、Daiying Zuo、Yingliang Wu、Weige Zhang

  DOI：10.1016/j.ejmech.2019.05.036

  日期：2019.9

  4-diaryl-1,2,5-oxadiazole-N-oxides. Among them, 7n′ and 7n′′ showed remarkable antiproliferative activities against three cancer cell lines in nanomolar concentrations. Interestingly, 7n′ inhibited tubulin polymerization much more efficiently than CA-4. Cellular mechanism investigation elucidated 7n′ disrupted the cellular microtubule structure, arrested cell cycle at G2/M phase and induces apoptosis. Molecular

  研究了康布雷他汀A-4（CA-4）的刚性类似物的结构活性关系，从而发现了一系列3,4-二芳基-1,2,5-恶二唑-N-氧化物。其中，7n'和7n''在纳摩尔浓度下对三种癌细胞显示出显着的抗增殖活性。有趣的是，7n'比CA-4更有效地抑制微管蛋白聚合。细胞机制研究阐明了7n'破坏了细胞微管结构，使细胞周期停滞在G 2 / M期并诱导了细胞凋亡。分子建模研究显示1,2,5-恶二唑-N-氧化环可增加与结合位点的氢键相互作用。这些结果为开发新的CA-4类似物提供了动力和进一步的指导。
• Cyclic α-Alkoxyphosphonium Salts from (2-(Diphenylphosphino)phenyl)methanol and Aldehydes and Their Application in Synthesis of Vinyl Ethers and Ketones via Wittig Olefination
  作者：Wenhua Huang、Hong-Ying Rong、Jie Xu

  DOI：10.1021/acs.joc.5b01031

  日期：2015.7.2

  synthesized from (2-(diphenylphosphino)phenyl)methanol and aldehydes in 36–89% yields. These phosphonium salts are bench-stable solids and undergo Wittig olefination with aldehydes under basic conditions (K2CO3 or t-BuOK) to form benzylic vinyl ethers, which are readily hydrolyzed to 1,2-disubstituted ethanones under acidic conditions. The formation mechanism of these phosphonium salts via hemiacetal

  环状α-烷氧基phosph盐是由（2-（二苯基膦基）苯基）甲醇和醛合成的，产率为36-89％。这些phospho盐是稳定的固体，并在碱性条件下（K 2 CO 3或叔丁基）与醛进行Wittig烯化反应，形成苄基乙烯基醚，该苄基乙烯基醚在酸性条件下容易水解为1,2-二取代的乙酮。还提出了这些phospho盐通过半缩醛的形成机理。