E-2-[(2-furyl)methylene]-5,6-dimethoxyindan-1-one | 889132-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: E-2-[(2-furyl)methylene]-5,6-dimethoxyindan-1-one
• 英文别名: (2E)-2-(furan-2-ylmethylidene)-5,6-dimethoxy-3H-inden-1-one
• CAS: 889132-05-2
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: MABJYIKLHGSPFL-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  E-2-[(2-furyl)methylene]-5,6-dimethoxyindan-1-one 在 HCl*Br₂ 作用下， 以 氯仿 为溶剂， 生成 C₁₆H₁₃BrO₄
  参考文献：
  名称：

  Design, synthesis and evaluation of novel 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4-substituted phenyl methanone analogues

  摘要：

  In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenylmethanone analogues were synthesized and were tested for their potential for treating AD disease. All the newly synthesized compounds were showing moderate to high AChE inhibitory activities, with compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4,5-trimethoxyphenylmethanone (5f) produced significant activities with 2.7 +/- 0.01 mu mol/L. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.042
• 作为产物：
  描述：

  糠醛 、 5,6-二甲氧基茚酮 在 sodium hydroxide 作用下， 以 乙醇 、 Petroleum ether 为溶剂， 生成 E-2-[(2-furyl)methylene]-5,6-dimethoxyindan-1-one
  参考文献：
  名称：

  抗分枝杆菌活性：合成新型3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物。

  摘要：

  在这项研究中，合成了一系列新型的3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物，并评估了其对结核分枝杆菌的抗分枝杆菌活性（ H（37）Rv和耐异烟肼结核分枝杆菌（INHR-MTB）。所有新合成的化合物均显示出中等至高抑制活性。发现化合物6,7-二甲氧基-3-（4-氯苯基）-4H-茚并[1,2-c]异恶唑（4b）是最有希望的化合物，对MTB H（37）Rv和INHR具有活性-MTB的最低抑菌浓度为0.22和0.34μM。

  DOI：

  10.3109/14756366.2010.529805

文献信息

• Highly Diastereoselective One-Pot Synthesis of Spiro{cyclopenta[<i>a</i>]indene-2,2‘-indene}diones from 1-Indanones and Aromatic Aldehydes
  作者：Pelayo Camps、Luis R. Domingo、Xavier Formosa、Carles Galdeano、Diana González、Diego Muñoz-Torrero、Sílvia Segalés、Mercè Font-Bardia、Xavier Solans

  DOI：10.1021/jo0600095

  日期：2006.4.1

  has been studied using DFT methods at the B3LYP/6-31G* level. The dimerization takes place through a process involving a Michael addition of a carbanion, obtained by deprotonation of 5g at the 3-position, to a second molecule of 5g, followed by an intramolecular Michael addition in the corresponding intermediate. The final protonation of the resulting anion accounts for the formation of the cis-fused

  在THF中用芳族醛和NaOEt处理1-茚满酮可通过四组分反应提供复杂的螺多环化合物，其中每种起始化合物的两个分子结合形成四个新的碳-碳键，从而形成了一个新的五个-元环，带有五个连续的立体定位中心，具有明确定义的相对构型。还形成了不同量的主要产物的次要差向异构体。茚满酮组分中甲氧基取代基的存在以及衍生自π-过量杂环的醛的使用使二聚步骤变慢了。在这些情况下，从预制的烯酮开始可获得更好的螺二聚体收率。该反应似乎是通过这样形成的烯酮的交叉羟醛缩合，脱水和二聚而发生的。已经使用DFT方法在B3LYP / 6-31G *水平上研究了5g。二聚化是通过以下过程进行的：将在3位的5g去质子化的碳负离子迈克尔加成至5g的第二个分子，然后在相应的中间体中进行分子内迈克尔加成。最终阴离子的最终质子化解释了顺式融合的五环系统的形成。
• Synthesis and antimycobacterial evaluation of novel 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-5,4-substituted phenyl methanone analogues
  作者：Mohamed Ashraf Ali、Jeyabalan Govinda Samy、Elumalai Manogaran、Velmurugan Sellappan、Mohamed Zaheen Hasan、Mohamed Jawed Ahsan、Suresh Pandian、Mohammad ShaharYar

  DOI：10.1016/j.bmcl.2009.10.034

  日期：2009.12

  In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenylmethanone analogues were synthesized and were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv and INH resistant M. tuberculosis. All the newly synthesized compounds were showing moderate to high inhibitory activities. The compound 5,6-dimethoxy-1-oxo-2,5-dihydro-1H-2-indenyl-4-fluorophenylmethanone (5g) was found to be the most promising compounds active against M. tuberculosis H(37)Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration 0.10 and 0.10 mu M. (C) 2009 Elsevier Ltd. All rights reserved.
• Ali, Mohamed A.; Ismail, Rusli; Choon, Tan S., Acta poloniae pharmaceutica, 2011, vol. 68, # 3, p. 343 - 348
  作者：Ali, Mohamed A.、Ismail, Rusli、Choon, Tan S.、Yoon, Yeong K.、Wei, Ang C.、Pandian, Suresh、Samy, Jeyabalan G.、De Clercq, Eric、Pannecouque, Christophe

  DOI：——

  日期：——
• Design, synthesis and evaluation of novel 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4-substituted phenyl methanone analogues
  作者：Mohamed Ashraf Ali、Mohammad Shahar Yar、Mohamed Zaheen Hasan、Mohamed Jawed Ahsan、Suresh Pandian

  DOI：10.1016/j.bmcl.2009.07.042

  日期：2009.9

  In present investigation, a series of substituted phenyl-5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenylmethanone analogues were synthesized and were tested for their potential for treating AD disease. All the newly synthesized compounds were showing moderate to high AChE inhibitory activities, with compound 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-2-indenyl-3,4,5-trimethoxyphenylmethanone (5f) produced significant activities with 2.7 +/- 0.01 mu mol/L. (C) 2009 Elsevier Ltd. All rights reserved.
• Antimycobacterial activity: synthesis of novel 3-(substituted phenyl)-6,7-dimethoxy-3a,4-dihydro-3<i>H</i>-indeno[1,2-<i>c</i>]isoxazole analogues
  作者：Mohamed Ashraf Ali、Rusli Ismail、Tan Soo Choon、Suresh Pandian、Mohamed Zaheen Hassan Ansari

  DOI：10.3109/14756366.2010.529805

  日期：2011.8.1

  this study, a series of novel 3-(substituted phenyl)-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c]isoxazole analogues were synthesized and evaluated for antimycobacterial activity against Mycobacterium tuberculosis (MTB) H(37)Rv and isoniazid resistant M. tuberculosis (INHR-MTB). All the newly synthesized compounds were showing moderate to high inhibitory activities. The compound 6,7-dimethoxy-3-(4-chloro

  在这项研究中，合成了一系列新型的3-（取代苯基）-6,7-二甲氧基-3a，4-二氢-3H-茚并[1,2-c]异恶唑类似物，并评估了其对结核分枝杆菌的抗分枝杆菌活性（ H（37）Rv和耐异烟肼结核分枝杆菌（INHR-MTB）。所有新合成的化合物均显示出中等至高抑制活性。发现化合物6,7-二甲氧基-3-（4-氯苯基）-4H-茚并[1,2-c]异恶唑（4b）是最有希望的化合物，对MTB H（37）Rv和INHR具有活性-MTB的最低抑菌浓度为0.22和0.34μM。