3-pentyl-deca-1,2-dien-4-yne

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3-pentyl-deca-1,2-dien-4-yne
• 英文别名: 8-Vinylidene-tridec-6-yne
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: QPIBJQGJOGGPSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 3-pentyl-deca-1,2-dien-4-yne 、 苯硼酸 在 manganese(IV) oxide 、 copper(II) bis(trifluoromethanesulfonate) 、 (S,S)-(-)-2,2'-异亚丙基双(4-叔丁基-2-恶唑啉) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以4.762%的产率得到
  参考文献：
  名称：

  Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes

  摘要：

  A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereo-selectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.

  DOI：

  10.1021/ol501022d
• 作为产物：
  描述：

  2-辛炔-1-醇 在 copper(l) iodide 、 四(三苯基膦)钯 氢氧化钾 、 二异丙胺 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 3-pentyl-deca-1,2-dien-4-yne
  参考文献：
  名称：

  Palladium-Catalyzed Regioselective Coupling of Propargylic Substrates with Terminal Alkynes. Application to the Synthesis of 1,2-Dien-4-ynes

  摘要：

  The palladium-catalyzed reaction of propargyl halides, tosylates and acetates with terminal alkynes is reported. The best yields are obtained from propargyl chlorides and 1-alkynes (i) in the presence of 2 equiv. of amine (triethylamine, diisopropylamine) in benzene, toluene or ethylacetate (ii) or in pure diisopropylamine. Propargyl acetates undergo the cross coupling reaction with moderate to high yields after modification of the general procedure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00115-0

文献信息

• An efficient palladium-catalysed reaction of propargyl halides tosylates and acetates with terminal alkynes
  作者：Sylvie Gueugnot、Gérard Linstrumelle

  DOI：10.1016/s0040-4039(00)79245-8

  日期：1993.6

  In the presence of palladium complexes and copper iodide, the reaction of propargyl halides with terminal alkynes proceeds rapidly to give conjugated allenynes in high yield. Propargyl acetates and tosylates are also suited to the preparation of such allenes.

  在钯配合物和碘化铜的存在下，炔丙基卤化物与末端炔烃的反应迅速进行，从而以高收率得到共轭的炔烃。炔丙基乙酸酯和甲苯磺酸酯也适合于制备这样的丙二烯。
• BAUDOUY, R.;GORE, J., J. CHEM. RES. MICROFICHE, 1981, N 9, 278-279
  作者：BAUDOUY, R.、GORE, J.

  DOI：——

  日期：——
• Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes
  作者：Taisuke Itoh、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ol501022d

  日期：2014.5.16

  A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereo-selectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
• Palladium-Catalyzed Regioselective Coupling of Propargylic Substrates with Terminal Alkynes. Application to the Synthesis of 1,2-Dien-4-ynes
  作者：Sylvie Condon-Gueugnot、Gérard Linstrumelle

  DOI：10.1016/s0040-4020(00)00115-0

  日期：2000.3

  The palladium-catalyzed reaction of propargyl halides, tosylates and acetates with terminal alkynes is reported. The best yields are obtained from propargyl chlorides and 1-alkynes (i) in the presence of 2 equiv. of amine (triethylamine, diisopropylamine) in benzene, toluene or ethylacetate (ii) or in pure diisopropylamine. Propargyl acetates undergo the cross coupling reaction with moderate to high yields after modification of the general procedure. (C) 2000 Elsevier Science Ltd. All rights reserved.