6-(2-methyl-4-oxo-4H-chromen-3-yl)hex-5-ynenitrile | 1233533-96-4

• 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-(2-methyl-4-oxo-4H-chromen-3-yl)hex-5-ynenitrile
• 英文别名: 6-(2-Methyl-4-oxochromen-3-yl)hex-5-ynenitrile
• CAS: 1233533-96-4
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: FQMMRAFSDKFUQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(2-methyl-4-oxo-4H-chromen-3-yl)hex-5-ynenitrile 在 copper(I) bromide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 10.0h， 以61%的产率得到4-[4-acetyl-5-(2-hydroxyphenyl)furan-2-yl]butanenitrile
  参考文献：
  名称：

  CuBr-catalyzed cascade reaction of 2-substituted-3-(1-alkynyl)chromones to synthesize functionalized 3-acylfurans

  摘要：

  A highly efficient CuBr-catalyzed domino reaction of 2-substituted-3-(1-alkynyl)chromones to synthesize functionalized 3-acylfurans has been developed. The reaction is mild, environmentally friendly and easily handled without the necessity for dry solvents and inert atmosphere. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.070

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。
• Phase Transfer Reagent Promoted Tandem Ring-Opening and Ring-Closing Reactions of Unique 3-(1-Alkynyl) Chromones
  作者：Yang Liu、Shiyu Jin、Liping Huang、Youhong Hu

  DOI：10.1021/acs.orglett.5b00721

  日期：2015.5.1

  promoted tandem ring-opening and ring-closing reaction of 3-(1-alkynyl) chromones has been developed. This process remarkably generates functionalized 3-acyl-2-substituted chromones. Interestingly, when 3-(hepta-1,6-diyn-1-yl)chromone derivatives are applied, a novel tetracyclic chromone scaffold can be obtained by a further intramolecular 4 + 2 cyclization.

  已经开发出相转移试剂促进3-（1-炔基）色酮的串联开环和闭环反应。该过程显着产生官能化的3-酰基-2-取代的色酮。有趣的是，当使用3-（庚-1,6-二炔-1-基）色酮衍生物时，可以通过进一步的分子内4 + 2环化获得新型的四环色酮支架。
• An Efficient Approach to Functionalized Benzo[<i>a</i>]xanthones through Reactions of 2-Methyl-3-(1-alkynyl)chromones with Electron-Deficient Chromone-Fused Dienes
  作者：Jian Gong、Fuchun Xie、Hong Chen、Youhong Hu

  DOI：10.1021/ol101496w

  日期：2010.9.3

  An efficient tandem process was developed to synthesize diversified benzo[a]xanthones from 2-methyl-3-(1-alkynyl)chromones with electron-deficient chromone-fused dienes. This unusual reaction, involving multiple steps and not requiring the use of transition metal catalysts or an inert atmosphere, results in the formation of three new C−C bonds and one C−O bond.

  开发了一种有效的串联方法，以从2-甲基-3-（1-炔基）色酮与电子不足的色酮稠合二烯合成多种苯并[ a ]氧杂蒽。这种不寻常的反应涉及多个步骤，不需要使用过渡金属催化剂或惰性气氛，导致形成三个新的C-C键和一个C-O键。
• An Organic Molecule Modulated Chemoselective Cyclization of Alkynyl Nitriles Tethered to 2-Alkyl Substituted Chromones with Multireactive Sites
  作者：Liping Huang、Yang Liu、Fuchun Xie、Youhong Hu

  DOI：10.1021/ol302964x

  日期：2012.12.21

  A small organic molecule phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate.
• Efficient Construction of a 3<i>C</i>-Xanthone-Linked 3<i>C</i>-Chromone Scaffold by Novel Double Michael Additions and Cyclizations
  作者：Fuchun Xie、Hong Chen、Youhong Hu

  DOI：10.1021/ol101100d

  日期：2010.7.2

  A novel base-promoted cascade reaction of 2-methyl-3-(1-alkynyl)chromones to produce a 3C-xanthone-linked 3C-chromone scaffold has been developed. This tandem process involves multiple reactions such as Michael additions/cyclizations under mild conditions without a transition metal catalyst and inert atmosphere.