9-(1H-indol-3-yl)-7-methoxy-3,3-dimethyl-2,3-dihydro-1H-xanthen-1(9H)-one | 1415682-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(1H-indol-3-yl)-7-methoxy-3,3-dimethyl-2,3-dihydro-1H-xanthen-1(9H)-one
• 英文别名: 9-(1h-Indol-3-yl)-7-methoxy-3,3-dimethyl-3,4-dihydro-2h-xanthen-1(9h)-one；9-(1H-indol-3-yl)-7-methoxy-3,3-dimethyl-4,9-dihydro-2H-xanthen-1-one
• CAS: 1415682-44-8
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: ZXUDAPKJCKDAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 2-羟基-5-甲氧基苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 sodium dodecyl-sulfate 、 L-脯氨酸 作用下， 以 水 为溶剂， 反应 2.0h， 以92%的产率得到9-(1H-indol-3-yl)-7-methoxy-3,3-dimethyl-2,3-dihydro-1H-xanthen-1(9H)-one
  参考文献：
  名称：

  An efficient one-pot organocatalytic synthesis of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones under mild aqueous micellar conditions

  摘要：

  An efficient and facile L-proline-catalyzed three-component coupling of 2-hydroxybenzaldehyde, 5,5-dimethyl-1,3-cyclohexanedione (dimedone), and indole has been accomplished under mild aqueous micellar conditions to deliver a small library of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones of potential biological relevance. Under optimized conditions [10 mol % of L-proline, water (2 mL), SDS (23 mg, 0.08 mmol), rt], the reaction was highly selective toward the target compound and essentially free from competitive two-component byproduct formation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.055

文献信息

• An efficient one-pot organocatalytic synthesis of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones under mild aqueous micellar conditions
  作者：Nemai C. Ganguly、Sushmita Roy、Pallab Mondal、Rajat Saha

  DOI：10.1016/j.tetlet.2012.10.055

  日期：2012.12

  An efficient and facile L-proline-catalyzed three-component coupling of 2-hydroxybenzaldehyde, 5,5-dimethyl-1,3-cyclohexanedione (dimedone), and indole has been accomplished under mild aqueous micellar conditions to deliver a small library of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones of potential biological relevance. Under optimized conditions [10 mol % of L-proline, water (2 mL), SDS (23 mg, 0.08 mmol), rt], the reaction was highly selective toward the target compound and essentially free from competitive two-component byproduct formation. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and molecular docking studies of oxochromenyl xanthenone and indolyl xanthenone derivatives as anti-HIV-1 RT inhibitors
  作者：Hanmant M. Kasralikar、Suresh C. Jadhavar、Sudhakar R. Bhusare

  DOI：10.1016/j.bmcl.2015.07.050

  日期：2015.9

  A series of novel oxochromenyl xanthenone and indolyl xanthenone derivatives were obtained by one-pot reaction of substituted salicylaldehyde, 4-hydroxy coumarin/indole and dimedone at ambient temperature condition using eco-friendly reusable ionic liquid [Hmim] HSO4 in ethanol solvent. Excellent yields, mild reaction condition, and simple experimental work-up procedure are some of the advantages of this method. The obtained derivatives were studied for their molecular docking as an anti-HIV-1 RT. All synthesized compounds from indolyl xanthenone and chromenyl xanthenone series were be docked into the non-nucleoside inhibitor binding pocket (NNIBP) of HIV-1 RT. Compounds 4r, 4j and 4k was found to be good around -12.487, -12.457, -12.256, respectively, with respective to native ligand TMC278, was found to be -13.413 which confirms that these compounds might have potent RT inhibition activity. (C) 2015 Elsevier Ltd. All rights reserved.