2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione | 67200-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione
• 英文别名: 2-(2,5-dimethoxybenzylidene)-2H-indene-1,3-dione；2-(2,5-dimethoxybenzylidene)-2H-indene-1,3‑dione；2-(2,5-dimethoxy-benzylidene)-indan-1,3-dione；2-(2,5-Dimethoxy-benzyliden)-indan-1,3-dion；2-[(2,5-Dimethoxyphenyl)methylidene]indene-1,3-dione
• CAS: 67200-96-8
• 化学式: C₁₈H₁₄O₄
• mdl: MFCD00405183
• 分子量: 294.307
• InChiKey: ABXCAOMREPMPCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以77%的产率得到3-(2,5-dimethoxyphenyl)-1,3-dihydro-4H-indeno[1,2-c]isoxazol-4-one
  参考文献：
  名称：

  由2-取代的1,3-茚满二酮衍生的新型三环化合物的合成及抗增殖活性

  摘要：

  摘要合成了一系列新的稠合的1，3-茚满二酮衍生物，并评估了其抗增殖活性。2-烯烃-1，3-茚满二酮衍生物已被用作许多三环化合物的前体。已经测试了后者的抗增殖活性。

  DOI：

  10.1134/s1070363220040209
• 作为产物：
  描述：

  对苯二甲醚 在 三氯化铝 、 乙醇 、 苯 作用下， 生成 2-(2,5-dimethoxybenzylidene)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  New parliament, new politics in Scotland

  摘要：

  DOI：

  10.1093/pa/53.3.605

文献信息

• Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides
  作者：Jie Huang、Shaofa Sun、Ping Ma、Jian Wang、Kevin Lee、Yalan Xing、Yang Wu、Gangqiang Wang

  DOI：10.1039/d1nj02886c

  日期：——

  This efficient and simple protocol features simple operations, mild conditions and excellent functional group compatibility. A variety of structurally interesting spiro-cyclopropanes were prepared in excellent yields and diastereomeric ratios (up to 97% yield and 20 : 1 dr). Also, ring expansion of the cyclopropanation product to quickly deliver a complex indeno[1,2-c]pyridazine structure showcased

  2-亚芳基-1,3-茚二酮和二甲基锍叶立德的高度非对映选择性螺环丙烷化反应已通过碱诱导环化开发。这种高效简单的方案具有操作简单、条件温和、功能组兼容性好等特点。以优异的产率和非对映体比率（高达 97% 的产率和 20:1 dr）制备了各种结构有趣的螺环丙烷。此外，环丙烷化产物的扩环以快速提供复杂的茚并[1,2- c ]哒嗪结构展示了该方法的有趣应用。
• Asymmetric synthesis of multicyclic spiro-1,3-indandiones via a cascade Michael/Michael reaction of curcumins and 2-arylidene-1,3-indandiones
  作者：Nian-hua Luo、Xiang Sun、Wen-tao Wei、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tetasy.2013.02.014

  日期：2013.4

  An organocatalytic cascade Michael/Michael reaction between curcumins and 2-arylidene-1,3-indandiones has been studied. Prolinol, chiral thiourea-tertiary amines, and cinchona alkaloids were evaluated as catalysts. Quinine was identified as the best catalyst for the transformation. Multicyclic spiro-1,3-indandiones were prepared in moderate to excellent yields, diastereoselectivities, and enantioselectivities. (c) 2013 Elsevier Ltd. All rights reserved.
• 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.
• New poly heterocyclic compounds based on pyrimidine-2-thiones: synthesis, evaluation of putative antiviral agents, DFT calculation, and molecular modeling
  作者：Salwa F. Mohamed、Heba S. Abd-Elghaffar、Abd El-Galil E. Amr、Dina H. Elnaggar、Eman S. Abou-Amra、Hanaa M. Hosny、Ashraf M. Mohamed、Dina N. Abd El-Shafy

  DOI：10.1016/j.molstruc.2023.136083

  日期：2023.11
• Synthesis and Anti-Proliferative Activity of Novel Tricyclic Compounds Derived from 2-Substituted 1,3-Indandione
  作者：H. S. Abd-Elghaffar、M. A. El-Hashash、S. F. Mohamed、A. A. Ibrahim、A. E. Amr、M. A. Al-Omar、E. S. Nossier

  DOI：10.1134/s1070363220040209

  日期：2020.4

  AbstractA new series of fused 1,3-indandione derivatives has been synthesized and evaluated for anti-proliferative activity. 2-Alkene-1,3-indandione derivatives have been used as the precursors of a number of tricyclic compounds. The latter have been tested for anti-proliferative activity.

  摘要合成了一系列新的稠合的1，3-茚满二酮衍生物，并评估了其抗增殖活性。2-烯烃-1，3-茚满二酮衍生物已被用作许多三环化合物的前体。已经测试了后者的抗增殖活性。