(E,E)-1,4-bis(l-menthyloxy)-1,3-butadiene | 197570-67-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E,E)-1,4-bis(l-menthyloxy)-1,3-butadiene
• 英文别名: (1S,2R,4R)-4-methyl-2-[(1E,3E)-4-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxybuta-1,3-dienoxy]-1-propan-2-ylcyclohexane
• CAS: 197570-67-5
• 化学式: C₂₄H₄₂O₂
• 分子量: 362.596
• InChiKey: GNUODHWJXCRTBN-OEOQQXQDSA-N

物化性质

• 沸点：
  474.4±28.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  马来酸酐 、 (E,E)-1,4-bis(l-menthyloxy)-1,3-butadiene 以 甲苯 为溶剂， 反应 3.0h， 以87%的产率得到(1R,2S,3R,6S)-3,6-bis-(l-menthyloxy)cyclohex-4-en-1,2-dicarboxylic acid anhydride
  参考文献：
  名称：

  Chiral (E,E)-1,4-dialkoxy-1,3-butadienes. 2. Conformational studies and Diels-Alder reactions with symmetric dienophiles

  摘要：

  The first examples of Diels-Alder reactions of chiral, C-2-symmetric (E,E)-1,4-dialkoxy-1,3-butadienes are described. The cycloadditions with maleic anhydride lead in all instances to the exclusive formation of the endo adducts. C-2h-Symmetric dienophiles such as fumaronitrile and diethyl fumarate react with variable diastereoselectivities; best results are obtained with the camphor-derived diene Id, whose reaction with diethyl fumarate takes place with complete facial selectivity. A theoretical analysis, using the SCF-MO procedure AM1, of the conformations of the dialkoxydienes has been used to rationalize the steric course of the cycloadditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00086-1
• 作为产物：
  描述：

  ethynyl, [2-isopropyl-5-methylcyclohexyl(1R,2S,5R)]ether 在 zirconocene hydrochloride 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以74%的产率得到(E,E)-1,4-bis(l-menthyloxy)-1,3-butadiene
  参考文献：
  名称：

  手性（E，E）-1，4-二烷氧基-1，3-丁二烯。1.立体选择性合成

  摘要：

  已经开发了由手性仲醇进行的两步全立体选择性合成（E，E）-1,4-二烷氧基-1,3-丁二烯的方法。关键步骤涉及衍生自手性醇的烷氧基乙炔的区域和立体选择性加氢锆化反应。中间体（E）-（2-烷氧基乙烯基）锆化合物在用氯化亚铜处理并热诱导分解相应的（2-烷氧基乙烯基）铜后，以中等收率得到二烷氧基丁二烯，但具有完全的（E，E）非对映选择性。

  DOI：

  10.1016/s0040-4039(97)01622-5

文献信息

• Chiral (E,E)-1,4-dialkoxy-1,3-butadienes. 2. Conformational studies and Diels-Alder reactions with symmetric dienophiles
  作者：Marina Virgili、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/s0040-4020(99)00086-1

  日期：1999.3

  The first examples of Diels-Alder reactions of chiral, C-2-symmetric (E,E)-1,4-dialkoxy-1,3-butadienes are described. The cycloadditions with maleic anhydride lead in all instances to the exclusive formation of the endo adducts. C-2h-Symmetric dienophiles such as fumaronitrile and diethyl fumarate react with variable diastereoselectivities; best results are obtained with the camphor-derived diene Id, whose reaction with diethyl fumarate takes place with complete facial selectivity. A theoretical analysis, using the SCF-MO procedure AM1, of the conformations of the dialkoxydienes has been used to rationalize the steric course of the cycloadditions. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Chiral (E,E)-1,4-dialkoxy-1,3-butadienes. 1. Stereoselective synthesis
  作者：Marina Virgili、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1016/s0040-4039(97)01622-5

  日期：1997.9

  A two step, totally stereoselective synthesis of (E,E)-1,4-dialkoxy-1,3-butadienes from chiral secondary alcohols has been developed. The key step involves the regio- and stereoselective hydrozirconation of alkoxyethynes derived from chiral alcohols; the intermediate (E)-(2-alkoxyvinyl)zirconium compounds, after treatment with cuprous chloride and thermally induced decomposition of the corresponding

  已经开发了由手性仲醇进行的两步全立体选择性合成（E，E）-1,4-二烷氧基-1,3-丁二烯的方法。关键步骤涉及衍生自手性醇的烷氧基乙炔的区域和立体选择性加氢锆化反应。中间体（E）-（2-烷氧基乙烯基）锆化合物在用氯化亚铜处理并热诱导分解相应的（2-烷氧基乙烯基）铜后，以中等收率得到二烷氧基丁二烯，但具有完全的（E，E）非对映选择性。