6-methoxy-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-methoxy-3-(phenylethynyl)-4H-chromen-4-one
• 英文别名: 6-Methoxy-3-(2-phenylethynyl)chromen-4-one；6-methoxy-3-(2-phenylethynyl)chromen-4-one
• 化学式: C₁₈H₁₂O₃
• 分子量: 276.291
• InChiKey: YHIODLRTLPOVBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-3-(phenylethynyl)-4H-chromen-4-one 在 air 、 copper(l) chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以45%的产率得到8-methoxy-2-phenyl-4H-furo[3,2-c]chromen-4-one
  参考文献：
  名称：

  Two Efficient Cascade Reactions to Synthesize Substituted Furocoumarins

  摘要：

  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.

  DOI：

  10.1021/jo800439y

文献信息

• CuCl2-catalyzed N O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles
  作者：Santosh K. Gudimella、Amanpreet Kaur、Ram Kumar、Sampak Samanta

  DOI：10.1016/j.tetlet.2020.152147

  日期：2020.7

  An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new CN bonds for imidazole ring synthesis. Gratifyingly, the implementation

  通过用几种肟酯与一组2-氨基氮杂氮杂铜进行铜催化的氮杂环化反应，开发了一种以良好至高收率的多种咪唑杂环杂环的铰接方法。上述环化反应可能是通过单电子转移过程进行的，这体现了一种新技术，该技术为咪唑环合成生成两个新的C N键。令人欣慰的是，该化学方法的实施可以进一步扩展为通过连续的C N键形成，合成带有呋喃[3,2- c ]亚甲基部分的新型稠合咪唑，随后是C（sp 2）-H功能化/ 5-内切-乙氧基环化（CC和C在铜（II）作为π亲电Lewis酸催化剂的情况下，原位生成带有环状烯酮的稠合咪唑。
• 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。
• Base-Promoted Cascade Reactions of 3-(1-Alkynyl)chromones with Pyridinium Ylides to Chromeno[2,3-<i>d</i>]azepine Derivatives
  作者：Yu-Fang Zhang、Wen-Di Duan、Jingjing Chen、Youhong Hu

  DOI：10.1021/acs.joc.8b03210

  日期：2019.4.5

  A base-promoted cascade reaction of 3-(1-alkynyl)chromones with pyridinium ylides has been developed to afford a novel chromeno[2,3-d]azepine scaffold in an efficient and economic manner. This tandem process involves multiple reactions including a Michael addition/deprotonation/alkyne–allene isomerization/cyclization and the subsequent 1,2-addition under mild conditions without a transition metal catalyst

  已经开发了碱促进的3-（1-炔基）色酮与吡啶鎓叶立德的级联反应，以有效和经济的方式提供了一种新型的铬诺[2,3- d ]]庚因支架。该串联过程涉及多个反应，包括迈克尔加成/去质子化/炔烃-丙二烯异构化/环化以及随后在温和条件下没有过渡金属催化剂的1,2-加成。
• 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）。