2-(2,3,4-trimethoxybenzylidene)-1H-indene-1,3(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2,3,4-trimethoxybenzylidene)-1H-indene-1,3(2H)-dione
• 英文别名: 2-[(2,3,4-Trimethoxyphenyl)methylidene]indene-1,3-dione
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: CZVPQVSYBCGDFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-3-((2,2,2-trifluoroethyl)imino)indolin-2-one 、 2-(2,3,4-trimethoxybenzylidene)-1H-indene-1,3(2H)-dione 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 以70 %的产率得到
  参考文献：
  名称：

  DABCO 通过 2-芳基/杂亚芳基-1H-茚-1,3(2H)-二酮与 N-2,2,2- 的 [3 + 2] 环加成促进 C-3 官能化螺吲哚的高度非对映和区域选择性构建环境条件下的三氟乙基靛红酮亚胺

  摘要：

  2-芳基/杂亚芳基-1H-茚-1,3( 2H )-二酮作为活化烯烃源在DABCO催化的N- 2,2,2-三氟乙基靛酮亚胺的[3+2]环加成反应中的应用已被披露。这种高效的 1,3-偶极环加成反应提供了多种带有螺吡咯烷连接的三氟甲基、具有四个连续立体中心的三氟甲基，具有良好至优异的产率和优异的非对映选择性。该方案的合成实用性是通过在室温下使用超低负载量的奎宁作为催化剂，展示具有两个邻位螺环季手性中心的螺环吡咯烷-羟吲哚的对映选择性结构，以良好的产率和优异的对映选择性（％3E90％ee）来建立的。 。

  DOI：

  10.1039/d2ra07141j
• 作为产物：
  描述：

  1,3-茚满二酮 、 2,3,4-三甲氧基苯甲醛 在 吡啶 作用下， 反应 1.0h， 以65%的产率得到2-(2,3,4-trimethoxybenzylidene)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  Benzylidine indane-1,3-diones: As novel urease inhibitors; synthesis, in vitro, and in silico studies

  摘要：

  Current study deals with the evaluation of indane-1,3-dione based compounds as new class of urease inhibitors. For that purpose, benzylidine indane-1,3-diones (1-30) were synthesized and fully characterized by different spectroscopic techniques including EI-MS, HREI-MS, H-1, and C-13 NMR. All synthetic molecules 1-30 were evaluated for urease inhibitory activity and showed good to moderate inhibitory potential within the range of (IC50 = 11.60 +/- 0.3-257.05 +/- 0.7 mu M) as compared to the standard acetohydroxamic acid (IC50 = 27.0 +/- 0.5 mu M). Compound 1 (IC50 = 11.60 +/- 0.3 mu M) was found to be most potent inhibitor amongst all derivatives. The key binding interactions of most active compounds within the enzyme pocket were evaluated through in silico studies.

  DOI：

  10.1016/j.bioorg.2018.09.030

文献信息

• Benzylidine indane-1,3-diones: As novel urease inhibitors; synthesis, in vitro, and in silico studies
  作者：Bilquees Bano、Kanwal、Khalid Mohammed Khan、Farida Begum、Muhammad Arif Lodhi、Uzma Salar、Ruqaiya Khalil、Zaheer Ul-Haq、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.09.030

  日期：2018.12

  Current study deals with the evaluation of indane-1,3-dione based compounds as new class of urease inhibitors. For that purpose, benzylidine indane-1,3-diones (1-30) were synthesized and fully characterized by different spectroscopic techniques including EI-MS, HREI-MS, H-1, and C-13 NMR. All synthetic molecules 1-30 were evaluated for urease inhibitory activity and showed good to moderate inhibitory potential within the range of (IC50 = 11.60 +/- 0.3-257.05 +/- 0.7 mu M) as compared to the standard acetohydroxamic acid (IC50 = 27.0 +/- 0.5 mu M). Compound 1 (IC50 = 11.60 +/- 0.3 mu M) was found to be most potent inhibitor amongst all derivatives. The key binding interactions of most active compounds within the enzyme pocket were evaluated through in silico studies.
• DABCO-promoted highly diastereo- and regioselective construction of C-3 functionalized spirooxindoles <i>via</i> [3 + 2] cycloaddition of 2-aryl/heteroarylidene-1<i>H</i>-indene-1,3(2<i>H</i>)-diones with <i>N</i>-2,2,2-trifluoroethylisatin ketimines at ambient conditions
  作者：Madavi S. Prasad、Sankar Bharani、Syed Mastan Sharief、Mudavath Ravi、Murugesan Sivaprakash、Biplob Borah、L. Raju Chowhan

  DOI：10.1039/d2ra07141j

  日期：——

  The application of 2-aryl/heteroarylidene-1H-indene-1,3(2H)-dione as an activated olefin source in the DABCO-catalyzed [3 + 2] cycloaddition with N-2,2,2-trifluoroethylisatin ketimines has been disclosed. This highly efficient 1,3-dipolar cycloaddition reaction offered a variety of trifluoro methyl group bearing spiro-pyrrolidine linked oxindoles with four consecutive stereocentres in good to excellent

  2-芳基/杂亚芳基-1H-茚-1,3( 2H )-二酮作为活化烯烃源在DABCO催化的N- 2,2,2-三氟乙基靛酮亚胺的[3+2]环加成反应中的应用已被披露。这种高效的 1,3-偶极环加成反应提供了多种带有螺吡咯烷连接的三氟甲基、具有四个连续立体中心的三氟甲基，具有良好至优异的产率和优异的非对映选择性。该方案的合成实用性是通过在室温下使用超低负载量的奎宁作为催化剂，展示具有两个邻位螺环季手性中心的螺环吡咯烷-羟吲哚的对映选择性结构，以良好的产率和优异的对映选择性（％3E90％ee）来建立的。 。