(4Z,6E)-4-phenyl-5,6-dipropyl-4,6-decadiene

• 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: (4Z,6E)-4-phenyl-5,6-dipropyl-4,6-decadiene
• 英文别名: 4-phenyl-5,6-dipropyldeca-(4Z,6E)-4,6-diene；[(4Z,6E)-5,6-dipropyldeca-4,6-dien-4-yl]benzene
• 化学式: C₂₂H₃₄
• 分子量: 298.512
• InChiKey: XFVWCTBJTIHNMD-OMRXDTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  碘苯 、 4-辛炔 在 正丁基锂 、 二氯二茂锆 、 N,N-二甲基丙烯基脲 、 copper(l) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以64%的产率得到(4Z,6E)-4-phenyl-5,6-dipropyl-4,6-decadiene
  参考文献：
  名称：

  Selective one carbon-carbon bond formation reaction of zirconacyclopentadienes with aryl iodides or alkynyl iodides

  摘要：

  Reaction of zirconacyclopentadienes with one equiv or two equiv of aryl iodides in the presence of CuCl and DMPU afforded mono-arylated diene derivatives in high yields with high selectivities. Treatment of zirconacyclopentadienes with one equiv of 2-thienyl iodide similarly gave thienyldienes in the presence of CuCl and DMPU, whereas the reaction with two equiv of 2-thienyl iodide produced thienyl iododiene derivatives in high yields. Zirconacyclopentadienes reacted with two equiv of alkynyl iodides to give iododienynes in good yields in the presence of CuCl. This is in sharp contrast to the reaction with two equiv of alkynyl iodides in the presence of CuCl and DMPU which provides dienediynes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10295-2

文献信息

• Nickel-catalysed hydroarylation of alkynes using arylboron compounds: selective synthesis of multisubstituted arylalkenes and aryldienes
  作者：Eiji Shirakawa、Go Takahashi、Teruhisa Tsuchimoto、Yusuke Kawakami

  DOI：10.1039/b107866f

  日期：2001.12.19

  Bis(1,5-cyclooctadiene)nickel was found to be an effective catalyst for the addition of the aryl group of arylboron compounds to alkynes in the presence of a proton source, which gives various multisubstituted alkenylarenes or dienylarenes selectively.

  双(1,5-环辛二烯)镍被发现是一种有效的催化剂，可以在质子源存在下，将芳基硼化合物的芳基添加到炔烃上，从而有选择性地生成各种多取代烯基芳烃或二烯基芳烃。
• Rh-catalyzed addition of boronic acids to alkynes for the synthesis of trisubstituted alkenes in a biphasic system - Mechanistic study and recycling of the Rh/m-TPPTC catalyst
  作者：Emilie Genin、Véronique Michelet、Jean-Pierre Genêt

  DOI：10.1016/j.jorganchem.2004.07.025

  日期：2004.11

  The versatile preparation of trisubstituted alkenes via selective Rh-catalyzed arylation of alkynes is described in water and in a water/toluene biphasic system. For hydrophobic alkyl alkynes, the reaction afforded either alkenes or dienes depending on the temperature and the solvent conditions. Aryl, heteroaryl, silylated and alkyl substituted alkynes reacted equally well with various boronic acids

  在水和水/甲苯双相体系中，通过选择性的Rh催化的炔烃芳基化反应制备三取代烯烃的通用方法，对于疏水性烷基炔烃，根据温度和溶剂条件，反应可生成烯烃或二烯。芳基，杂芳基，甲硅烷基化和烷基取代的炔烃与各种硼酸反应良好，从而区域选择性地以高收率（65-99％）生成官能化的烯基衍生物。在甲苯/水混合物或水中对这种机理进行了研究，涉及乙烯基铑络合物。公开了具有优异的产率（92-96％）和烯烃纯度的Rh / m- TPPTC系统的有效再循环。
• Hydrophenylation of internal alkynes with boronic acids catalysed by a Ni–Zn hydroxy double salt-intercalated anionic rhodium(<scp>iii</scp>) complex
  作者：Takayoshi Hara、Nozomi Fujita、Nobuyuki Ichikuni、Karen Wilson、Adam F. Lee、Shogo Shimazu

  DOI：10.1039/c5cy01139f

  日期：——

  [Rh(OH)₆]³⁻ intercalated Ni–Zn mixed basic salt (Rh/NiZn) acts as an efficient catalyst for the hydrophenylation of internal alkynes with arylboronic acids under mild conditions.

  [Rh(OH)₆]³⁻插层Ni-Zn混合碱性盐（Rh/NiZn）在温和条件下催化内部炔烃与芳基硼酸的加氢苯基化反应中表现出高效催化作用。
• Efficient synthesis of trisubstituted alkenes in an aqueous–organic system using a versatile and recyclable Rh/ m -TPPTC catalyst
  作者：Emilie Genin、Véronique Michelet、Jean-Pierre Genêt

  DOI：10.1016/j.tetlet.2004.03.136

  日期：2004.5

  We have found that the use of [Rh(cod)OH](2) associated with the water-soluble ligand m-TPPTC was highly efficient for the Rh-catalyzed arylation of alkynes. Aryl and alkyl alkynes were transformed to alkenes using 3 mol% rhodium catalyst and 2.5 equiv of boronic acid Lit 100degreesC in a biphasic water/toluene system in 80-99% yield. The reaction was found to be totally regioselective for alkyl arylalkynes and alkyl silylated alkynes. The Rh/m-TPPTC system was for the first tune recycled with no loss of the activity and with excellent Purity of the desired alkene. (C) 2004 Elsevier Ltd. All rights reserved.
• Selective one carbon-carbon bond formation reaction of zirconacyclopentadienes with aryl iodides or alkynyl iodides
  作者：Tamotsu Takahashi、Wen-Hua Sun、Chanjuan Xi、Ubayama Haruka、Zhenfeng Xi

  DOI：10.1016/s0040-4020(97)10295-2

  日期：1998.1

  Reaction of zirconacyclopentadienes with one equiv or two equiv of aryl iodides in the presence of CuCl and DMPU afforded mono-arylated diene derivatives in high yields with high selectivities. Treatment of zirconacyclopentadienes with one equiv of 2-thienyl iodide similarly gave thienyldienes in the presence of CuCl and DMPU, whereas the reaction with two equiv of 2-thienyl iodide produced thienyl iododiene derivatives in high yields. Zirconacyclopentadienes reacted with two equiv of alkynyl iodides to give iododienynes in good yields in the presence of CuCl. This is in sharp contrast to the reaction with two equiv of alkynyl iodides in the presence of CuCl and DMPU which provides dienediynes. (C) 1997 Elsevier Science Ltd. All rights reserved.