cis-(2R,6R)-2-methyl-6-((E)-2,4,6-trimethylstyryl)tetrahydropyran | 1314532-33-6

• 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: cis-(2R,6R)-2-methyl-6-((E)-2,4,6-trimethylstyryl)tetrahydropyran
• 英文别名: cis-(2R,6R)-2-methyl-6-((E)-styryl)-tetrahydropyran；(2R,6R)-2-methyl-6-[(E)-2-(2,4,6-trimethylphenyl)ethenyl]oxane
• CAS: 1314532-33-6
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: WCMKIUUNXYXXBF-GUFYHEMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (R)-6-hepten-2-ol acetate 在 Hoveyda-Grubbs catalyst second generation 、 iron(III) chloride hexahydrate 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 cis-(2R,6R)-2-methyl-6-((E)-2,4,6-trimethylstyryl)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

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.