2-<3.4-Dimethoxy-phenyl>-3-phenyl-acrylnitril | 5508-10-1

• 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-<3.4-Dimethoxy-phenyl>-3-phenyl-acrylnitril
• 英文别名: 2-(3.4-Dimethoxy-phenyl)-3-phenyl-acrylnitril；2-(3,4-Dimethoxyphenyl)-3-phenylprop-2-enenitrile
• CAS: 5508-10-1
• 化学式: C₁₇H₁₅NO₂
• mdl: MFCD05258777
• 分子量: 265.312
• InChiKey: FXBALPNGWRQTOL-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  409.9±45.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<3.4-Dimethoxy-phenyl>-3-phenyl-acrylnitril 在 碘 、 methyloxirane 作用下， 以 乙腈 为溶剂， 生成 9-cyano-6,7-dimethoxyphenanthrene
  参考文献：
  名称：

  Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities

  摘要：

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.008
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 、 苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到2-<3.4-Dimethoxy-phenyl>-3-phenyl-acrylnitril
  参考文献：
  名称：

  PHENANTHROINDOLIZIDINE DERIVATIVE AND NF kB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT

  摘要：

  公开号：

  EP2351753B1

文献信息

• Chemoselective α-Alkylation and α-Olefination of Arylacetonitriles with Alcohols <i>via</i> Iron-Catalyzed Borrowing Hydrogen and Dehydrogenative Coupling
  作者：Ramachandra Reddy Putta、Simin Chun、Seok Beom Lee、Junhwa Hong、Seung Hyun Choi、Dong-Chan Oh、Suckchang Hong

  DOI：10.1021/acs.joc.2c02050

  日期：2022.12.16

  borrowing hydrogen or α-olefination by dehydrogenative coupling methods. Designing and developing high-performance earth-abundant catalysts that can procure different products from the same starting materials remain a great challenge. Herein, we report an iron(0) catalyst system that achieves chemoselectivity between borrowing hydrogen and dehydrogenative coupling protocols by simply changing the base. A

  α-烷基腈和α-烯烃腈在有机合成和药物化学中非常重要。然而，不同类型的催化剂用于通过借氢实现腈的α-烷基化或通过脱氢偶联方法实现α-烯烃化。设计和开发高性能的地球丰富的催化剂，可以从相同的起始材料中获得不同的产品仍然是一个巨大的挑战。在此，我们报告了一种铁 (0) 催化剂系统，该系统通过简单地改变碱基来实现借氢和脱氢偶联方案之间的化学选择性。广泛的腈类和醇类，包括苄醇、直链脂肪醇、脂环醇、杂环醇和烯丙醇，被选择性且有效地转化为相应的产物。机理研究表明反应机理通过脱氢途径进行。这种铁催化方案对环境无害且原子效率高，可释放 H2和 H 2 O 作为绿色副产物。
• PHENANTHROINDOLIZIDINE DERIVATIVE AND NF kB INHIBITOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：EP2351753B1

  公开（公告）日：2015-02-11
• Reduction and Benzylation by Means of Benzyl Alcohol. V. A New Synthesis of α,β-Diarylpropionic Acids and the Corresponding Nitriles¹
  作者：Moshe Avramoff、Yaër Sprinzak

  DOI：10.1021/ja01535a059

  日期：1958.1
• Asymmetric synthesis of phenanthroindolizidine alkaloids with hydroxyl group at the C14 position and evaluation of their antitumor activities
  作者：Takashi Ikeda、Takashi Yaegashi、Takeshi Matsuzaki、Syusuke Hashimoto、Seigo Sawada

  DOI：10.1016/j.bmcl.2010.11.008

  日期：2011.1

  The asymmetric total synthesis of the strongly cytotoxic phenanthroindolizidine alkaloid 3 was achieved. Using the same route, various derivatives were also synthesized. Cytotoxicity of those synthetic compounds was evaluated and compounds 19, 23, and 27 demonstrated potent cytotoxicities similar to that of 3. The in vivo antitumor efficacy of selected compounds was also evaluated and 23 demonstrated moderate antitumor efficacy. (C) 2010 Elsevier Ltd. All rights reserved.