(E)-tridec-3-ene-2,8-diol | 1221972-41-3

• 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: (E)-tridec-3-ene-2,8-diol
• CAS: 1221972-41-3
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: LONSOYZWJYUUFZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (E)-tridec-3-ene-2,8-diol 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到cis-2-pentyl-6-((E)-propenyl)-tetrahydropyran
  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：

  5-己烯醛 在 吡啶 、 4-二甲氨基吡啶 、 Hoveyda-Grubbs catalyst second generation 、 cerium(III) chloride heptahydrate 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 71.92h， 生成 (E)-tridec-3-ene-2,8-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.