7-methoxy-3,3-dimethyl-9-(1-methyl-1H-indol-3-yl)-2,3-dihydro-1H-xanthen-1(9H)-one | 1415682-50-6

• 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: 7-methoxy-3,3-dimethyl-9-(1-methyl-1H-indol-3-yl)-2,3-dihydro-1H-xanthen-1(9H)-one
• 英文别名: 7-methoxy-3,3-dimethyl-9-(1-methylindol-3-yl)-4,9-dihydro-2H-xanthen-1-one
• CAS: 1415682-50-6
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: DDZYFJRMAAYHCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基-5-甲氧基苯甲醛 、 1-甲基吲哚 、 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86%的产率得到7-methoxy-3,3-dimethyl-9-(1-methyl-1H-indol-3-yl)-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.