2-<(E,E)-buta-1',3'-dien-1'-yl>-1,3,3-trimethylcyclohexene | 74423-06-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-<(E,E)-buta-1',3'-dien-1'-yl>-1,3,3-trimethylcyclohexene
• 英文别名: 2-buta-1,3-dienyl-1,3,3-trimethyl-cyclohexene；2-Buta-1,3-dienyl-1,3,3-trimethyl-cyclohexen；1,3,3-Trimethyl-2-(butadien-1,3-yl)-cyclohexen；Megastigmatriene；2-[(1E)-buta-1,3-dienyl]-1,3,3-trimethylcyclohexene
• CAS: 74423-06-6
• 化学式: C₁₃H₂₀
• 分子量: 176.302
• InChiKey: BWPHCNAZKLXPHW-RMKNXTFCSA-N

物化性质

• 沸点：
  239.102±7.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.874±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
• 保留指数：
  1483

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (E)-4-(2,6,6-三甲基-1-环己烯-1-基)-3-丁烯-2-醇乙酸酯 在 四(三苯基膦)钯 三苯基膦 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以88%的产率得到2-<(E,E)-buta-1',3'-dien-1'-yl>-1,3,3-trimethylcyclohexene
  参考文献：
  名称：

  通过钯（0）配合物的催化活化作用，通过氢化物转移，还原乙酸烯丙酯

  摘要：

  通过氢化物试剂通过与Pd（0）配合物的催化活化作用，通过氢化物还原置换将乙酸烯丙酯还原为烯烃。在不存在氢化物的情况下，乙酸烯丙酯在DMSO溶剂中提供共轭二烯。

  DOI：

  10.1016/s0040-4039(00)93615-3

文献信息

• Palladium-Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes: A Highly Stereoselective Synthesis of 8,18-¹³C₂-Labeled Retinal
  作者：Akimori Wada、Yasuhiro Ieki、Saeko Nakamura、Masayoshi Ito

  DOI：10.1055/s-2005-865294

  日期：——

  Here we report that enol nonaflates exhibit higher reactivity than the corresponding enol triflates in palladium-catalyzed cross-coupling reactions with various (vinyl)tributylstannanes and acetylenes. We also highlight the reaction of a vinyl nonaflate, containing two 1 3 C-labeled carbon atoms with an alkenyl stannane, which afforded the trisubstituted E-olefin stereoselectively in high yield. The

  在这里，我们报告烯醇九氟甲磺酸酯在钯催化的与各种（乙烯基）三丁基锡烷和乙炔的交叉偶联反应中表现出比相应的烯醇三氟甲磺酸酯更高的反应性。我们还强调了含有两个 1 3 C 标记的碳原子的乙烯基九烷基锡与烯基锡烷的反应，它以高产率立体选择性地提供了三取代的 E-烯烃。然后将 E-烯烃转化为相应的全 E-视黄醛。
• Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes
  作者：Akimori Wada、Yasuhiro Ieki、Masayoshi Ito

  DOI：10.1055/s-2002-32602

  日期：——

  stereoselective synthesis of trienes and dienynes was developed by palladium catalyzed cross coupling reactions of an enol nonaflate with (vinyl)tributylstannanes and acetylenes in good to excellent yields. Here, the enol nonaflate exhibited a higher reactivity compared with the corresponding enol triflate in the coupling reactions.

  通过钯催化烯醇壬酯与（乙烯基）三丁基锡烷和乙炔的交叉偶联反应，开发了一种立体选择性合成三烯和二炔的新方法，收率良好至极好。在这里，与相应的烯醇三氟甲磺酸酯相比，烯醇九氟甲磺酸酯在偶联反应中表现出更高的反应性。
• The suzuki reaction in stereocontrolled polyene synthesis: Retinol (vitamin A), its 9- and/or 13-demethyl analogs, and related 9-demethyl-dihydroretinoids
  作者：Alicia Torrado、Beatriz Iglesias、Susana López、Angel R. de Lera

  DOI：10.1016/0040-4020(94)01108-c

  日期：1995.2

  A new synthesis of retinol (vitamin A) and 9- and/or 13-demethylretinols, with essentially complete control of regio- and stereochemistry, is described which is based on the thallium-accelerated, palladium-catalyzed cross-coupling reactions of (E)-1-alkenylboronic acids and (E)-1-alkenyl iodides (Suzuki reaction). The procedure has also been extended to the stereocontrolled synthesis of a series of 9-demethyl-dihydroretinoids of potential biological interest.
• Kandel, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 205, p. 994,995
  作者：Kandel

  DOI：——

  日期：——
• Reductive displacement of allylic acetates by hydride transfer via catalytic activation by palladium(0) complexes
  作者：Robert O. Hutchins、Keith Learn、Robert P. Fulton

  DOI：10.1016/s0040-4039(00)93615-3

  日期：1980.1

  Allylic acetates are reduced to alkenes by reductive displacement by hydride reagents via catalytic activation with Pd(0) complexes. In the absence of hydrides, allylic acetates afford conjugated dienes in DMSO solvent.

  通过氢化物试剂通过与Pd（0）配合物的催化活化作用，通过氢化物还原置换将乙酸烯丙酯还原为烯烃。在不存在氢化物的情况下，乙酸烯丙酯在DMSO溶剂中提供共轭二烯。