3-ethynyl-2H-chromene | 395642-36-1

• 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-ethynyl-2H-chromene
• CAS: 395642-36-1
• 化学式: C₁₁H₈O
• 分子量: 156.184
• InChiKey: WDWFRVHNMABOEF-UHFFFAOYSA-N

物化性质

• 沸点：
  249.1±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-ethynyl-2H-chromene 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 13.0h， 生成 N-((2H-chromen-3-yl)ethynyl)-N-methylmethanesulfonamide
  参考文献：
  名称：

  Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes

  摘要：

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.

  DOI：

  10.1021/ja412634w
• 作为产物：
  描述：

  2H-色烯-3-甲醛 在 三苯基膦 、 锌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 7.0h， 生成 3-ethynyl-2H-chromene
  参考文献：
  名称：

  通过功能性吡啶基锌试剂和钯催化的交叉偶联反应有效合成新的杂类胡萝卜素

  摘要：

  描述了由 6-溴-2-吡啶基氯化锌 (11) 聚合合成带有色烯环和吡啶基或乙炔基吡啶基部分的杂芳烃类化合物 4、5a 和 5b。这种新的功能杂芳基锌试剂很容易从 2,6-二溴吡啶中获得，可以进行选择性钯催化的碳-碳键形成反应，以产生相应的 6-取代-2-溴吡啶 13。 13得到锌衍生物14，随后在钯催化条件下与4-碘苯甲酸乙酯偶联得到杂芳烃4。取代的溴吡啶13或三氟甲磺酸酯22与适当的炔烃在Sonogashira条件下偶联得到相应的杂芳烃5a、5b和6 .

  DOI：

  10.1002/1099-0690(200111)2001:22<4207::aid-ejoc4207>3.0.co;2-3

文献信息

• Process for the Preparation of 2H-Chromene-3-Carbamate Derivatives
  申请人：Broadbelt Brian

  公开号：US20100298580A1

  公开（公告）日：2010-11-25

  Compounds of formula I, V, VI and II, and processes for their preparation, wherein R 1 , R 2 and R 3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group; and R 4 is alkyl or aryl. There is also provided a process for preparing a compound of formula B from the compounds of formula V and I.

  公式I、V、VI和II的化合物及其制备方法，其中R1、R2和R3相同或不同，表示氢、卤素、烷基、烷氧基、羟基、硝基、烷基羰基氨基、烷基氨基或二烷基氨基基团; 而R4是烷基或芳基。还提供了一种从公式V和I的化合物制备公式B化合物的方法。
• Efficient Syntheses of New Heteroarotinoids through Functional Pyridylzinc Reagents and Palladium-Catalyzed Cross-Coupling Reactions
  作者：Mouâd Alami、Jean-François Peyrat、Larbi Belachmi、Jean-Daniel Brion

  DOI：10.1002/1099-0690(200111)2001:22<4207::aid-ejoc4207>3.0.co;2-3

  日期：2001.11

  rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible from 2,6-dibromopyridine, may undergo a selective palladium-catalyzed carbon−carbon bond-forming reaction to yield the corresponding 6-substituted-2-bromopyridines 13. Further manipulation of the remaining bromine atom in 13

  描述了由 6-溴-2-吡啶基氯化锌 (11) 聚合合成带有色烯环和吡啶基或乙炔基吡啶基部分的杂芳烃类化合物 4、5a 和 5b。这种新的功能杂芳基锌试剂很容易从 2,6-二溴吡啶中获得，可以进行选择性钯催化的碳-碳键形成反应，以产生相应的 6-取代-2-溴吡啶 13。 13得到锌衍生物14，随后在钯催化条件下与4-碘苯甲酸乙酯偶联得到杂芳烃4。取代的溴吡啶13或三氟甲磺酸酯22与适当的炔烃在Sonogashira条件下偶联得到相应的杂芳烃5a、5b和6 .
• Zn(II)- or Ag(I)-Catalyzed 1,4-Metathesis Reactions between 3-En-1-ynamides and Nitrosoarenes
  作者：Sagar Ashok Gawade、Deepak B. Huple、Rai-Shung Liu

  DOI：10.1021/ja412634w

  日期：2014.2.26

  Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.