(E)-8-acetoxy-2-hydroxy-8-phenyl-oct-6-enoic acid ethyl ester | 1221972-39-9

• 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: (E)-8-acetoxy-2-hydroxy-8-phenyl-oct-6-enoic acid ethyl ester
• 英文别名: (E)-8-acetoxy-2-hydroxy-8-phenyloct-6-enoic acid ethyl ester；ethyl (E)-8-acetyloxy-2-hydroxy-8-phenyloct-6-enoate
• CAS: 1221972-39-9
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: HPEUHKTUHHPFDR-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-8-acetoxy-2-hydroxy-8-phenyl-oct-6-enoic acid ethyl ester 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 trans-6-((E)-styryl)-tetrahydropyran-2-carboxylic acid ethyl ester 、 cis-6-((E)-styryl)-tetrahydropyran-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans

  摘要：

  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.

  DOI：

  10.1021/ol100422d
• 作为产物：
  描述：

  alpha-乙烯基苄基乙酸酯 、 ethyl 2-hydroxyhept-6-enoate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以57%的产率得到(E)-8-acetoxy-2-hydroxy-8-phenyl-oct-6-enoic acid ethyl ester
  参考文献：
  名称：

  FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans

  摘要：

  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.

  DOI：

  10.1021/ol100422d

文献信息

• 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.