(5R,6R,9R,10R)-5,6,9,10-diepoxy-13-(tert-butyldimethylsilyloxy)tridec-1-ene | 1287305-43-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (5R,6R,9R,10R)-5,6,9,10-diepoxy-13-(tert-butyldimethylsilyloxy)tridec-1-ene
• 英文别名: 3-[(2R,3R)-3-[2-[(2R,3R)-3-but-3-enyloxiran-2-yl]ethyl]oxiran-2-yl]propoxy-tert-butyl-dimethylsilane
• CAS: 1287305-43-4
• 化学式: C₁₉H₃₆O₃Si
• 分子量: 340.579
• InChiKey: TWFQEJOPXUSNSG-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  34.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,6R,9R,10R)-5,6,9,10-diepoxy-13-(tert-butyldimethylsilyloxy)tridec-1-ene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成
  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：

  (4E,8E)-dodeca-4,8-diene-1,12-diol 在 Shi's ketone 、 sodium tetraborate decahydrate 、 potassium peroxomonosulfate 、 四丁基硫酸氢铵 、 sodium hexamethyldisilazane 、 edetate disodium 、 sodium hydride 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲醇缩甲醛 、 水 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 4.0h， 生成 (5R,6R,9R,10R)-5,6,9,10-diepoxy-13-(tert-butyldimethylsilyloxy)tridec-1-ene
  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.