gymnopalyne A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: gymnopalyne A
• 英文别名: 3-(3-Chloroprop-1-ynyl)isochromen-1-one；3-(3-chloroprop-1-ynyl)isochromen-1-one
• 化学式: C₁₂H₇ClO₂
• 分子量: 218.639
• InChiKey: GKFUWYMNGFBDGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻羧基苯乙酸 在 palladium diacetate 、 三乙胺 、 三苯基膦 、 三氯氧磷 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 11.0h， 生成 gymnopalyne A
  参考文献：
  名称：

  Efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of 3′-hydroxycorfin and gymnopalynes A analogues

  摘要：

  An efficient method involving copper-free Pd(OAc)(2)/Ruphos-catalyzed Sonogashira coupling strategy for a variety of 3-alkynyl isochromen-1-ones has been developed. Sonogashira coupling in the presence of catalytic system-Pd(OAc)(2)/Ruphos, Et3N base, and tetrahydrofuran solvent under aqueous and room temperature conditions, provided novel 3-(allcynyl)-1H-isochromen-1-ones in excellent yields. The methodology has also been extended toward natural isochromen-1-one-3'-hydroxycorfin and gymnopalynes A analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.059

文献信息

• Palladium/copper-catalyzed tandem Sonogashira coupling/lactonization of methyl 2-(2′,2′-dibromovinyl)benzoate with terminal alkynes: Facile access to 3-alkynyl isocoumarins
  作者：Xiaozu Liu、Guojun Chen、Yuxiang Zhou、Peijun Liu

  DOI：10.1016/j.tetlet.2018.07.017

  日期：2018.8

  An efficient palladium/copper-catalyzed tandem Sonogashira reaction/lactonization of methyl 2-(2′,2′-dibromovinyl)benzoate with terminal alkynes has been developed. This facile and direct approach furnishes a variety of 3-alkynyl isocoumarins in moderate to good yields under mild reaction conditions. Furthermore, this method enables concise total synthesis of natural products 3′-hydroxycorfin and gymnopalynes

  已经开发了一种有效的钯/铜催化串联Sonogashira反应/ 2-（2'，2'-二溴乙烯基）苯甲酸甲酯与末端炔烃的内酯化。这种简便而直接的方法可在温和的反应条件下以中等至良好的产率提供各种3-炔基异香豆素。此外，该方法能够简明地完全合成天然产物3'-羟基皮质醇和裸gym草烯酮A。
• Efficient copper-free Pd(OAc)2/Ruphos-catalyzed Sonogashira coupling in the preparation of 3′-hydroxycorfin and gymnopalynes A analogues
  作者：Changalaraya Dasaradhan、Yadavalli Suneel Kumar、Fazlur-Rahman Nawaz Khan、Euh Duck Jeong、Eun Hyuk Chung

  DOI：10.1016/j.tetlet.2014.11.059

  日期：2015.1

  An efficient method involving copper-free Pd(OAc)(2)/Ruphos-catalyzed Sonogashira coupling strategy for a variety of 3-alkynyl isochromen-1-ones has been developed. Sonogashira coupling in the presence of catalytic system-Pd(OAc)(2)/Ruphos, Et3N base, and tetrahydrofuran solvent under aqueous and room temperature conditions, provided novel 3-(allcynyl)-1H-isochromen-1-ones in excellent yields. The methodology has also been extended toward natural isochromen-1-one-3'-hydroxycorfin and gymnopalynes A analogues. (C) 2014 Elsevier Ltd. All rights reserved.