(Z)-8-methyl-1-(2,4,6-trimethyl-phenyl)-non-2-ene-1,7-diol | 1221972-53-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-8-methyl-1-(2,4,6-trimethyl-phenyl)-non-2-ene-1,7-diol
• 英文别名: (Z)-8-methyl-1-(2,4,6-trimethylphenyl)non-2-ene-1,7-diol
• CAS: 1221972-53-7
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: TUCFDLZUIBLMIG-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-8-methyl-1-(2,4,6-trimethyl-phenyl)-non-2-ene-1,7-diol 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 cis-2-isopropyl-6-[(E)-2-(2,4,6-trimethyl-phenyl)-vinyl]-tetrahydropyran 、 trans-2-isopropyl-6-[(E)-2-(2,4,6-trimethyl-phenyl)-vinyl]-tetrahydropyran
  参考文献：
  名称：

  FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives

  摘要：

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.112
• 作为产物：
  描述：

  5-己烯醛 在 2,6-二甲基吡啶 、 喹啉 、 正丁基锂 、 四丁基氟化铵 、 氢气 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 8.25h， 生成 (Z)-8-methyl-1-(2,4,6-trimethyl-phenyl)-non-2-ene-1,7-diol
  参考文献：
  名称：

  FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives

  摘要：

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.112

文献信息

• FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans
  作者：Amandine Guérinot、Anna Serra-Muns、Christian Gnamm、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1021/ol100422d

  日期：2010.4.16

  The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.
• FeCl3·6H2O-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from ζ-hydroxy allylic derivatives
  作者：Amandine Guérinot、Anna Serra-Muns、Charlélie Bensoussan、Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2011.03.112

  日期：2011.7

  A highly diastereoselective iron-catalyzed synthesis of substituted cis-2,6-tetrahydropyrans from zeta-hydroxy allylic derivatives is described. The FeCl3 center dot 6H(2)O-induced epimerization of the formed 2-alkenyl 6-substituted tetrahydropyrans is the key reaction to account for the high diastereoselectivities observed. (C) 2011 Elsevier Ltd. All rights reserved.