[(3E,5E)-6-ethoxy-3-methylhexa-3,5-dienoxy]methylbenzene | 808762-77-8

• 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: [(3E,5E)-6-ethoxy-3-methylhexa-3,5-dienoxy]methylbenzene
• CAS: 808762-77-8
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: LOFWFLHLHIGYKT-KJZHCDIESA-N

物化性质

• 沸点：
  358.6±35.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(3E,5E)-6-ethoxy-3-methylhexa-3,5-dienoxy]methylbenzene 在 platinum on activated charcoal 氢气 、 对苯二酚 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 86.5h， 生成 (3aR,4S,7S,7aS)-4-ethoxy-7-methyl-7-(2-phenylmethoxyethyl)-4,5,6,7a-tetrahydro-3aH-2-benzofuran-1,3-dione
  参考文献：
  名称：

  A concise synthesis of the functionalized [5–7–6] tricyclic skeleton of guanacastepene A

  摘要：

  The six membered ring of guanacastepene A was constructed by a Diels-Alder reaction of 1,1,4-trisubstituted diene to set up the correct relative stereochernistry at the C8 quaternary center and the remote C5 stereocenter. In 10 efficient steps from the Diels-Alder adduct 9, the desired highly functionalized [5-7-6] tricyclic skeleton 2 was synthesized. Key steps involve trimethylsilyl chloride (TMSCl) assisted Michael addition to form enol ether and the usage of the enol ether in the following intramolecular Mukaiyama aldol reaction to form the middle seven membered ring of guanacastepene A. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.187
• 作为产物：
  描述：

  (E)-4-iodo-3-methylbut-3-en-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 四乙基氯化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 [(3E,5E)-6-ethoxy-3-methylhexa-3,5-dienoxy]methylbenzene
  参考文献：
  名称：

  A concise synthesis of the functionalized [5–7–6] tricyclic skeleton of guanacastepene A

  摘要：

  The six membered ring of guanacastepene A was constructed by a Diels-Alder reaction of 1,1,4-trisubstituted diene to set up the correct relative stereochernistry at the C8 quaternary center and the remote C5 stereocenter. In 10 efficient steps from the Diels-Alder adduct 9, the desired highly functionalized [5-7-6] tricyclic skeleton 2 was synthesized. Key steps involve trimethylsilyl chloride (TMSCl) assisted Michael addition to form enol ether and the usage of the enol ether in the following intramolecular Mukaiyama aldol reaction to form the middle seven membered ring of guanacastepene A. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.187

文献信息

• Highly efficient palladium-catalyzed hydrostannation of ethyl ethynyl ether
  作者：Ian P. Andrews、Ohyun Kwon

  DOI：10.1016/j.tetlet.2008.09.147

  日期：2008.12

  The palladium-catalyzed hydrostannation of acetylenes is widely exploited in organic synthesis as a means of forming vinyl stannanes for use in palladium-catalyzed cross-coupling reactions. Application of this methodology to ethyl ethynyl ether results in an enol ether that is challenging to isolate from the crude reaction mixture because of incompatibility with typical silica gel chromatography. Reported

  钯催化的乙炔氢化锡化在有机合成中被广泛用作形成用于钯催化的交叉偶联反应的乙烯基锡烷的手段。将此方法应用于乙炔基醚会产生烯醇醚，由于与典型的硅胶色谱法不兼容，因此很难从粗反应混合物中分离出来。本文报道了一种使用 0.1% 钯 (0) 催化剂和 1.0 当量氢化三丁基锡对乙基乙炔醚进行钯催化氢化锡化的高效程序。获得的产物是区域异构体的混合物，可以通过β-异构体的专有反应进行。这种方法具有很高的重现性；相对于以前报道的程序，它更经济，并且涉及更容易的纯化程序。
• A concise synthesis of the functionalized [5–7–6] tricyclic skeleton of guanacastepene A
  作者：Xiaohui Du、Hiufung V. Chu、Ohyun Kwon

  DOI：10.1016/j.tetlet.2004.09.187

  日期：2004.11

  The six membered ring of guanacastepene A was constructed by a Diels-Alder reaction of 1,1,4-trisubstituted diene to set up the correct relative stereochernistry at the C8 quaternary center and the remote C5 stereocenter. In 10 efficient steps from the Diels-Alder adduct 9, the desired highly functionalized [5-7-6] tricyclic skeleton 2 was synthesized. Key steps involve trimethylsilyl chloride (TMSCl) assisted Michael addition to form enol ether and the usage of the enol ether in the following intramolecular Mukaiyama aldol reaction to form the middle seven membered ring of guanacastepene A. (C) 2004 Elsevier Ltd. All rights reserved.