(E,2S,7S,8S)-7,8-epoxyundec-3-en-2,11-diol | 1287305-38-7

• 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: (E,2S,7S,8S)-7,8-epoxyundec-3-en-2,11-diol
• 英文别名: (E,2S)-6-[(2S,3S)-3-(3-hydroxypropyl)oxiran-2-yl]hex-3-en-2-ol
• CAS: 1287305-38-7
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: GOANICDMICUIFY-ZHNWDCKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E,2S,7S,8S)-7,8-epoxyundec-3-en-2,11-diol 在 silica gel 作用下， 以 乙酸乙酯 为溶剂， 反应 48.0h， 以100%的产率得到(E,1S,6S)-1-[(2R)-oxolan-2-yl]hept-4-ene-1,6-diol
  参考文献：
  名称：

  Pd^II-Catalyzed Cascade Reaction with 1,3-Chirality Transfer; Stereoselective Synthesis of Chiral Nonracemic 2,2′-THF−THF Ring Units

  摘要：

  A Pd-II-catalyzed cascade reaction of chiral nonracemic allylic alcohols possessing an internal mono- or diepoxide and a terminal alcohol provided a contiguous THF-THF ring unit stereospecifically. The cyclization takes place in a 5-exo-tet-5-exo-trig fashion with high chirality transfer through a syn-S(N)2' like process for the formation of the internal THF ring. Chiral bis- and tris-THF-THF ring units were effectively prepared from acyclic precursors by the Pd-catalyzed reaction.

  DOI：

  10.1021/ol2005984
• 作为产物：
  描述：

  在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E,2S,7S,8S)-7,8-epoxyundec-3-en-2,11-diol
  参考文献：
  名称：

  Pd^II-Catalyzed Cascade Reaction with 1,3-Chirality Transfer; Stereoselective Synthesis of Chiral Nonracemic 2,2′-THF−THF Ring Units

  摘要：

  A Pd-II-catalyzed cascade reaction of chiral nonracemic allylic alcohols possessing an internal mono- or diepoxide and a terminal alcohol provided a contiguous THF-THF ring unit stereospecifically. The cyclization takes place in a 5-exo-tet-5-exo-trig fashion with high chirality transfer through a syn-S(N)2' like process for the formation of the internal THF ring. Chiral bis- and tris-THF-THF ring units were effectively prepared from acyclic precursors by the Pd-catalyzed reaction.

  DOI：

  10.1021/ol2005984

文献信息

• Pd^II-Catalyzed Cascade Reaction with 1,3-Chirality Transfer; Stereoselective Synthesis of Chiral Nonracemic 2,2<b>′</b>-THF−THF Ring Units
  作者：Jun’ichi Uenishi、Yuhei Fujikura、Nobuyuki Kawai

  DOI：10.1021/ol2005984

  日期：2011.5.6

  A Pd-II-catalyzed cascade reaction of chiral nonracemic allylic alcohols possessing an internal mono- or diepoxide and a terminal alcohol provided a contiguous THF-THF ring unit stereospecifically. The cyclization takes place in a 5-exo-tet-5-exo-trig fashion with high chirality transfer through a syn-S(N)2' like process for the formation of the internal THF ring. Chiral bis- and tris-THF-THF ring units were effectively prepared from acyclic precursors by the Pd-catalyzed reaction.