2-(4-methoxybenzoyl)benzaldehyde | 112533-14-9

• 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: 2-(4-methoxybenzoyl)benzaldehyde
• 英文别名: 3-(4-methoxyphenyl)formylbenzaldehyde；3-(4-methoxybenzoyl)benzaldehyde；3-(4-Methoxy-benzoyl)-benzaldehyde
• CAS: 112533-14-9
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: MZMXPXDGYUKROQ-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±30.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-acetyl-3-((5-(tert-butyl)-1H-imidazol-4-yl)methylene)piperazine-2,5-dione 、 2-(4-methoxybenzoyl)benzaldehyde 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以25%的产率得到(3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(3-(4-methoxybenzoyl)benzylidene)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059
• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)苯甲腈 在 重铬酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 2-(4-methoxybenzoyl)benzaldehyde
  参考文献：
  名称：

  Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

  摘要：

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.059

文献信息

• 氘代脱氢3-苯甲酰苯基阿夕斯丁类化合物及其制备方法和在制备抗肿瘤的药物中的应用
  申请人：青岛海洋生物医药研究院股份有限公司

  公开号：CN107286137A

  公开（公告）日：2017-10-24

  本发明提供了氘代脱氢3‑苯甲酰苯基阿夕斯丁类化合物及其制备方法和在制备抗肿瘤的药物中的应用，该类化合物具有通式(I)的结构，其合成方法包括：先将二乙酰基哌嗪二酮与氘醛化合物b发生缩合反应，形成含氘杂环化合物c，再与3‑苯甲酰苯甲醛类化合物发生缩合反应形成氘代脱氢3‑苯甲酰苯基阿夕斯丁类化合物。同时，本发明也提供了一种高效的高氘代率的氘醛中间体及含氘杂环中间体及其合成方法，同时也提供了一种高效的3‑苯甲酰苯甲醛类化合物的合成方法。经实验证明本发明提供的氘代脱氢3‑苯甲酰苯基阿夕斯丁类化合物具有抑制胰腺癌生长的作用。本发明提供了研究与开发所述相关化合物的抗胰腺癌的药物的方法。
• Streptocyanine as an activation mode of amine catalysis for the conversion of pyridine rings to benzene rings
  作者：Tatsuya Morofuji、Shota Nagai、Airi Watanabe、Kota Inagawa、Naokazu Kano

  DOI：10.1039/d2sc06225a

  日期：——

  Consequently, the alkene moiety in the starting pyridines is incorporated into the benzene ring of the products. Pyridiniums bearing various alkene moieties were efficiently converted to formyl-substituted benzene derivatives. Mechanistic studies support the postulation that the present catalytic process was intermediated by streptocyanine. In this reaction system, streptocyanine could be regarded as a

  胺催化剂已成为有机合成中的宝贵工具。亚胺、烯胺和烯胺自由基阳离子物种是胺催化的代表性活化模式。然而，开发新的胺催化激活模式以实现新的合成策略仍然非常令人期待。在此，我们报告链花青作为一种新的胺催化激活模式，能够将吡啶环骨架编辑为苯环。 3-位带有烯基取代基的吡啶的N-芳基化生成相应的N-芳基吡啶鎓。所得吡啶与催化量的哌啶反应，得到链花青中间体。催化生成的链花青通过闭环反应形成苯环，从而释放胺催化剂。因此，起始吡啶中的烯烃部分被并入产物的苯环中。带有各种烯烃部分的吡啶鎓被有效地转化为甲酰基取代的苯衍生物。机理研究支持目前的催化过程是由链花青介导的假设。在该反应体系中，链花青可以被视为一种新的胺催化活化模式。
• Palladium-catalyzed carbonylative coupling of aryl triflates with organostannanes
  作者：Antonio M. Echavarren、J. K. Stille

  DOI：10.1021/ja00213a032

  日期：1988.3
• Synthesis and structure–activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents
  作者：Yuri Yamazaki、Makiko Sumikura、Yurika Masuda、Yoshiki Hayashi、Hiroyuki Yasui、Yoshiaki Kiso、Takumi Chinen、Takeo Usui、Fumika Yakushiji、Barbara Potts、Saskia Neuteboom、Michael Palladino、George Kenneth Lloyd、Yoshio Hayashi

  DOI：10.1016/j.bmc.2012.05.059

  日期：2012.7

  KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the dike-topiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC50 value against HT-29 cells (IC50 = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. (C) 2012 Elsevier Ltd. All rights reserved.