3-(3-hydroxy-3-methylbut-1-ynyl) chromen-4-one | 935273-46-4

• 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: 3-(3-hydroxy-3-methylbut-1-ynyl) chromen-4-one
• 英文别名: 3-(3-hydroxy-3-methyl-1-butynyl)chromone；3-(3-Hydroxy-3-methylbut-1-ynyl)chromen-4-one
• CAS: 935273-46-4
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: DMKWTMHEQGLEAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-3-methylbut-1-ynyl) 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55%的产率得到2-(1-Hydroxy-1-methylethyl)-4H-furo[3,2-c][1]benzopyran-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
• 作为产物：
  描述：

  色酮 在 bis-triphenylphosphine-palladium(II) chloride ammonium cerium(IV) nitrate 、 碘 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 16.58h， 生成 3-(3-hydroxy-3-methylbut-1-ynyl) chromen-4-one
  参考文献：
  名称：

  Pd-mediated synthesis of substituted benzenes fused with carbocycle/heterocycle

  摘要：

  报道了一种新型的无铜条件下，钯催化的一锅多组分耦合反应，用于构建苯环与碳环或杂环的并环结构。

  DOI：

  10.1039/b612770c

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。
• C-Alkynylation of Chromones by Sonogashira Reaction
  作者：Tamás Patonay、István Pazurik、Anita Ábrahám

  DOI：10.1071/ch13006

  日期：——

  Sonogashira reaction of bromochromones and -flavones with a bromine atom on their benzene or heterocyclic ring with various terminal alkynes gave the desired products with nearly the same efficiency as the previously used iodine derivatives. The coupling reactions were performed in the presence of [tetrakis(triphenylphosphine)palladium(0)], copper(i) co-catalyst, and triethylamine, resulting in the

  溴苯并二氢吡喃酮和-黄酮与苯或杂环上的溴原子与各种末端炔烃的Sonogashira反应产生所需的产物，其效率几乎与以前使用的碘衍生物相同。偶联反应在[四（三苯基膦）钯（0）​​]，铜（i）助催化剂和三乙胺的存在下进行，导致形成了许多迄今未知的炔基化氧杂环，并为进一步的应用提供了证据这些O-杂环的反应。通过除去三甲基甲硅烷基保护基制备具有乙炔基官能团的苯并在第二次交叉偶联反应中用作末端炔烃。
• Pd-mediated synthesis of substituted benzenes fused with carbocycle/heterocycle
  作者：Nalivela Kumara Swamy、Lakshmi Kumar Tatini、J. Moses Babu、Pazhanimuthu Annamalai、Manojit Pal

  DOI：10.1039/b612770c

  日期：——

  A new Pd-catalyzed one-pot multicomponent coupling reaction for the construction of benzene ring fused with carbocycle or heterocycle under a Cu-free condition is described.

  报道了一种新型的无铜条件下，钯催化的一锅多组分耦合反应，用于构建苯环与碳环或杂环的并环结构。
• 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.