6-(4-oxo-4H-chromen-3-yl)hex-5-ynenitrile

• 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-(4-oxo-4H-chromen-3-yl)hex-5-ynenitrile
• 英文别名: 6-(4-Oxochromen-3-yl)hex-5-ynenitrile
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: AIYRFWMRMCIRFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-oxo-4H-chromen-3-yl)hex-5-ynenitrile 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 21.0h， 以64%的产率得到4-(4-Oxofuro[3,2-c]chromen-2-yl)butanenitrile
  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

文献信息

• A novel multicomponent reaction to synthesize substituted furo[3,2-c]chromenes via a Pd-catalyzed cascade process
  作者：Lizhi Zhao、Gang Cheng、Youhong Hu

  DOI：10.1016/j.tetlet.2008.10.025

  日期：2008.12

  A novel one-pot three-component reaction for the synthesis of multisubstituted furo[3,2-c]chromenes using 3-(1-alkynyl)chromones, aryl iodides, and alcohols is developed via Pd-catalyzed cascade 1,4-addition and cyclization. This synthetic approach efficiently generates two C–O bonds and one C–C bond to construct diverse furo[3,2-c]chromenes structures.

  通过钯催化的级联1,4-加成反应，开发了一种新颖的一锅三组分反应，该反应可使用3-（1-炔基）色酮，碘代芳基和醇类合成多取代的呋喃并[3,2- c ]色烯。和环化。这种合成方法可以有效地产生两个C–O键和一个C–C键，以构建不同的呋喃[3,2- c ]苯二甲基结构。
• 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。
• 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。
• Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins
  作者：Gang Cheng、Youhong Hu

  DOI：10.1021/jo800439y

  日期：2008.6.1

  We have developed two efficient one-pot reactions to generate furo[3,2-c]coumarins and chlorofuro[3,2-c]coumarins through addition/cyclization/oxidation and chlorination. One cascade addition/cyclization/oxidation sequence of 1 with H2O in the presence of 20% CuCl as Lewis acid under an air atmosphere generated the 2-substituted-4H-furo[3,2-c]chromen-4-one 2. Another sequence in the presence of 10% CuBr and excess CuCl2 as the oxidant afforded the 3-chloro2-substituted-4H-furo[3,2-c]chromen-4-one 3.