6-nitro-3-(phenylethynyl)-4H-chromen-4-one

• 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: 6-nitro-3-(phenylethynyl)-4H-chromen-4-one
• 英文别名: 6-Nitro-3-(2-phenylethynyl)chromen-4-one
• 化学式: C₁₇H₉NO₄
• 分子量: 291.263
• InChiKey: KLXBYHXKAZWHRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-nitro-3-(phenylethynyl)-4H-chromen-4-one 在 甲烷磺酸 、 水 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 以51%的产率得到8-Nitro-2-phenylfuro[3,2-c]chromen-4-one
  参考文献：
  名称：

  通过级联加成-环化-氧化一锅合成呋喃香豆素。

  摘要：

  已开发出一种新颖的一锅级联加成环氧化法，用于呋喃[3,2-c]香豆素的区域选择性合成；反应温和且易于处理，无需干燥溶剂和惰性气氛。

  DOI：

  10.1039/b705315k
• 作为产物：
  描述：

  3-iodo-6-nitro-4H-chromen-4-one 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-nitro-3-(phenylethynyl)-4H-chromen-4-one
  参考文献：
  名称：

  Three-Component One-Pot Approach to Synthesize Benzopyrano[4,3-d]pyrimidines

  摘要：

  A novel benzopyrano[4,3-d]pyrimidine scaffold was generated via a three-component one-pot reaction from iodochromone, alkyne, and an amidine through a Sonogashira coupling, condensation, and cycloaddition. This combinatorial synthetic approach provides an efficient, easy construction of a diversified heterocyclic compounds library.

  DOI：

  10.1021/cc100173b

文献信息

• Base-Promoted One-Pot Tandem Reaction of 3-(1-Alkynyl)chromones under Microwave Irradiation to Functionalized Amino-Substituted Xanthones
  作者：Yang Liu、Liping Huang、Fuchun Xie、Youhong Hu

  DOI：10.1021/jo1013614

  日期：2010.9.17

  A base-promoted one-pot tandem reaction has been developed from 3-(1-alkynyl)chromones with various acetonitriles to afford functionalized amino-substituted xanthones 3 under microwave irradiation. This tandem process involves multiple reactions, such as Michael addition/cyclization/1,2-addition, without a transition metal catalyst. This method provides an efficient approach to build up natural product-like

  由3-（1-炔基）色酮与各种乙腈开发了碱促进的一锅串联反应，以在微波辐射下提供官能化的氨基取代的氧杂蒽3。该串联过程涉及多个反应，例如迈克尔加成/环化/ 1,2-加成，而没有过渡金属催化剂。该方法提供了一种有效的方法来快速建立类似天然产物的多样化的氨基取代的蒽酮骨架。
• Synthesis of novel functional polycyclic chromones through Michael addition and double cyclizations
  作者：Yang Liu、Liping Huang、Fuchun Xie、Xuxing Chen、Youhong Hu

  DOI：10.1039/c0ob01000f

  日期：——

  2-halobenzylic nitriles (esters or amides) for the synthesis of novel functional polycyclic chromenones has been developed. This tandem process involves multiple reactions, such as Michael addition and double cyclizations without a transition metal catalyst.

  从简单的3-（1-炔基）色酮与2-卤代苄腈（酯或酰胺）的碱促进的微波辅助一锅串联反应已得到开发，用于合成新型功能性多环色酮。该串联过程涉及多个反应，例如迈克尔加成和没有过渡金属催化剂的双环化。
• A Base-Promoted Tandem Reaction of 3-(1-Alkynyl)chromones with 1,3-Dicarbonyl Compounds: An Efficient Approach to Functional Xanthones
  作者：Lizhi Zhao、Fuchun Xie、Gang Cheng、Youhong Hu

  DOI：10.1002/anie.200902618

  日期：2009.8.17

  No need for a transition‐metal catalyst is characteristic for the tandem process presented herein to obtain functionalized xanthones. The sequence involves multiple reactions, such as Michael addition‐elimination/cyclization/1,2‐addition/elimination reactions (see scheme).

  此处介绍的用于获得官能化氧杂蒽的串联方法的特征是不需要过渡金属催化剂。该序列涉及多个反应，例如迈克尔加成-消除/环化/ 1,2-加成/消除反应（请参阅方案）。
• A base-promoted desalicyloylative dimerization of 3-(1-alkynyl)chromones: An unusual approach to 2-alkynyl xanthones
  作者：Fuchun Xie、Xuan Pan、Shijun Lin、Youhong Hu

  DOI：10.1039/b925234g

  日期：——

  A novel base-promoted cascade desalicyloylative dimerization of 3-(1-alkynyl)chromones to produce 2-alkynyl xanthones has been developed. This tandem process involves multiple reactions, such as Michael additions/cyclizations/desalicyloylation without a transition metal catalyst and inert atmosphere.

  一种新型的碱促进的3-（1-炔基）色酮的级联去水杨酰化二聚化反应 2-炔基黄嘌呤已被开发出来。该串联过程涉及多个反应，例如在没有过渡金属催化剂和惰性气氛下的迈克尔加成/环化/去水杨酰化。
• Direct Synthesis of Functional Azaxanthones by Using a Domino Three-Component Reaction
  作者：Jianwei Yan、Ming Cheng、Feng Hu、Youhong Hu

  DOI：10.1021/ol3013099

  日期：2012.6.15

  NH aldimines, generated in situ from the corresponding aldehydes by reaction with ammonium acetate, serve as nitrogen nucleophiles in reactions with 3-(1-alkynyl)chromones and 3-cyanochromones that generate functionalized azaxanthones. These processes take place under mild conditions that do not require dry solvents. The products of the reactions described represent new chemical entities. We believe that the newly developed cascade process will serve as a potent method for the synthesis of N-heterocycles and in diversity-oriented synthesis.