(E)-3-ethyl-1-phenyl-3-hexen-1-yne

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-ethyl-1-phenyl-3-hexen-1-yne
• 英文别名: 1-phenyl-3-ethylhex-3E-en-1-yne；[(E)-3-ethylhex-3-en-1-ynyl]benzene
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: BISMNNDDEFTYBG-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-己炔 在 四(三苯基膦)钯 四丁基氟化铵 、 silver(I) chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.0h， 生成 (E)-3-ethyl-1-phenyl-3-hexen-1-yne
  参考文献：
  名称：

  钯催化的三异丙基甲硅烷基乙炔选择性交联到内部和末端未活化的炔烃上。

  摘要：

  具有N，N'-双[2-（二苯基膦基）苯基] ami基酸酯（DPFAM）作为配体的双核和单核钯络合物催化三异丙基甲硅烷基乙炔（TIPSA）交叉加成到未活化的内部炔烃上，从而选择性地产生炔烃。当使用具有PPh 3，TDMPP，dppe或dppf的钯催化剂时，获得了TIPSA的二聚体作为主要产物。尽管收率中等，TIPSA与几个末端炔烃的反应也选择性地产生了交叉加合物。

  DOI：

  10.1021/ol071326g

文献信息

• Bis(acetylacetonato)copper Catalyzed Cross-coupling Reaction of Alkenyldicyclohexylborane with 1-Bromo-1-alkyne or 3-Bromo-1-propene
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1246/bcsj.56.2855

  日期：1983.9

  Bis(acetylacetonato)copper is capable of catalyzing cross-coupling reaction of alkenyldicyclohexylborane with 1-bromo-1-alkyne or 3-bromo-1-propene to give conjugated (E)-enyne or (E)-1,4-diene in a highly stereoselective manner, respectively.

  双(乙酰丙酮)铜能够催化烯基双环己基硼与1-溴-1-炔或3-溴-1-丙烯的交叉偶联反应，分别生成高度立体选择性的共轭(E)-炔或(E)-1,4-二烯。
• Alkynylzirconation of Alkynes and Application to One-Pot Bisalkynylation of Alkynes
  作者：Yuanhong Liu、Zhenqi Zhong、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1021/jo026037e

  日期：2002.10.1

  Stereocontrolled alkynylzirconation of unactivated alkynes was achieved by the reaction of an alkyne with Cp2ZrEt2 and alkynyl halide in this order. After hydrolysis of the alkynylzirconation product, trisubstituted enyne derivatives were obtained in good yields. Functionalized enynes were also prepared by the reaction of the alkynylzirconation products with a variety of electrophiles. Subsequent addition of the second alkynyl halide to the alkynylzirconation products provided an in situ protocol for bisalkynylation of alkynes into (Z)-enediynes in good yields.
• Palladium-Catalyzed Selective Cross-Addition of Triisopropylsilylacetylene to Internal and Terminal Unactivated Alkynes
  作者：Naofumi Tsukada、Satoshi Ninomiya、Yoshimi Aoyama、Yoshio Inoue

  DOI：10.1021/ol071326g

  日期：2007.7.1

  Dinuclear and mononuclear palladium complexes having N,N'-bis[2-(diphenylphosphino)phenyl]amidinate (DPFAM) as a ligand catalyzed the cross-addition of triisopropylsilylacetylene (TIPSA) to unactivated internal alkynes, giving enynes selectively. When palladium catalysts having PPh3, TDMPP, dppe, or dppf were used, dimers of TIPSA were obtained as major products. The reactions of TIPSA with several

  具有N，N'-双[2-（二苯基膦基）苯基] ami基酸酯（DPFAM）作为配体的双核和单核钯络合物催化三异丙基甲硅烷基乙炔（TIPSA）交叉加成到未活化的内部炔烃上，从而选择性地产生炔烃。当使用具有PPh 3，TDMPP，dppe或dppf的钯催化剂时，获得了TIPSA的二聚体作为主要产物。尽管收率中等，TIPSA与几个末端炔烃的反应也选择性地产生了交叉加合物。