(E)-methyl 2-((2,3-dioxoindolin-1-yl)methyl)-3-phenylacrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 2-((2,3-dioxoindolin-1-yl)methyl)-3-phenylacrylate
• 英文别名: methyl (E)-2-[(2,3-dioxo-2,3-dihydro-1H-1-indolyl)methyl]-3-phenyl-2-propionate；methyl (E)-2-[(2,3-dioxoindol-1-yl)methyl]-3-phenylprop-2-enoate
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: QGHCEJVQHPUAAK-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-((2,3-dioxoindolin-1-yl)methyl)-3-phenylacrylate 、 苯 在 palladium(II) trifluoroacetate 、 silver(I) acetate 、 三甲基乙酸 作用下， 反应 24.0h， 以81%的产率得到methyl 2-((2,3-dioxoindolin-1-yl)methyl)-3,3-diphenylacrylate
  参考文献：
  名称：

  钯氧化催化的Heckation螯合辅助的立体和区域选择性合成四取代的烯烃。

  摘要：

  通过钯催化的，螯合辅助的氧化Heck芳基化反应方案，可以从带有取代基的带有方向基团的三取代烯烃以完全立体和区域选择性的方式高效合成四取代烯烃。四取代烯烃的立体选择性和区域选择性以及出色的收率均源于钯中间物与导向基团之间的螯合作用，使钯中间体稳定。

  DOI：

  10.1002/adsc.201200306
• 作为产物：
  描述：

  methyl 2-(bromomethyl)-3-phenylacrylate 、 靛红 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以87%的产率得到(E)-methyl 2-((2,3-dioxoindolin-1-yl)methyl)-3-phenylacrylate
  参考文献：
  名称：

  Synthesis, antitubercular and anticancer activity of new Baylis–Hillman adduct-derived N-cinnamyl-substituted isatin derivatives

  摘要：

  Baylis-Hillman adduct-derived N-cinnamyl-substituted isatin derivatives were synthesized and evaluated for their antitubercular activity on Mycobacterium tuberculosis H(37)Rv strain ATCC 27294 by agar dilution method. Anticancer activity for the same compounds was also screened on four different cell lines: Chinese hamster ovary (CHO cells), Colo 205 (human colon cancer), Sup-T1 (human lymphoma) and C6 glioma (rat glioma) by MTT assay method. The compounds (3j-l) have shown significant activity against Mycobacterium strain and the compound 3l has shown specific cytotoxic activity.

  DOI：

  10.1007/s00044-013-0787-x

文献信息

• Palladium‐Catalyzed, Chelation‐Assisted Stereo‐ and Regioselective Synthesis of Tetrasubstituted Olefins by Oxidative Heck Arylation
  作者：Hyun Seung Lee、Ko Hoon Kim、Sung Hwan Kim、Jae Nyoung Kim

  DOI：10.1002/adsc.201200306

  日期：2012.9.17

  An efficient synthesis of tetrasubstituted olefins was achieved via a palladium‐catalyzed, chelation‐assisted oxidative Heck arylation protocol from trisubstituted olefins bearing a tether with a directing group in a completely stereo‐ and regioselective manner. The stereo‐ and regioselectivity as well as excellent yields of tetrasubstituted olefins originated from the stabilization of a palladium

  通过钯催化的，螯合辅助的氧化Heck芳基化反应方案，可以从带有取代基的带有方向基团的三取代烯烃以完全立体和区域选择性的方式高效合成四取代烯烃。四取代烯烃的立体选择性和区域选择性以及出色的收率均源于钯中间物与导向基团之间的螯合作用，使钯中间体稳定。
• Synthesis, antitubercular and anticancer activity of new Baylis–Hillman adduct-derived N-cinnamyl-substituted isatin derivatives
  作者：Sriramoju Bharath Kumar、Mettu Ravinder、Golla Kishore、Vaidya Jayathirtha Rao、Perumal Yogeeswari、Darmarajan Sriram

  DOI：10.1007/s00044-013-0787-x

  日期：2014.4

  Baylis-Hillman adduct-derived N-cinnamyl-substituted isatin derivatives were synthesized and evaluated for their antitubercular activity on Mycobacterium tuberculosis H(37)Rv strain ATCC 27294 by agar dilution method. Anticancer activity for the same compounds was also screened on four different cell lines: Chinese hamster ovary (CHO cells), Colo 205 (human colon cancer), Sup-T1 (human lymphoma) and C6 glioma (rat glioma) by MTT assay method. The compounds (3j-l) have shown significant activity against Mycobacterium strain and the compound 3l has shown specific cytotoxic activity.