7-chloro-9-(1H-indol-3-yl)-3,3,6-trimethyl-2,3-dihydro-1H-xanthen-1(9H)-one | 1415682-46-0

• 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-chloro-9-(1H-indol-3-yl)-3,3,6-trimethyl-2,3-dihydro-1H-xanthen-1(9H)-one
• 英文别名: 7-chloro-9-(1H-indol-3-yl)-3,3,6-trimethyl-4,9-dihydro-2H-xanthen-1-one
• CAS: 1415682-46-0
• 化学式: C₂₄H₂₂ClNO₂
• 分子量: 391.897
• InChiKey: MFVBPXVGTVGPSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 5-氯-2-羟基-4-甲基苯甲醛 、 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86%的产率得到7-chloro-9-(1H-indol-3-yl)-3,3,6-trimethyl-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.