[4-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]-2-methylidenebutyl]-trimethylsilane | 1221900-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: [4-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]-2-methylidenebutyl]-trimethylsilane
• CAS: 1221900-09-9
• 化学式: C₁₇H₃₂O₂Si
• 分子量: 296.525
• InChiKey: VDMVUAYZCKZCSR-BFYDXBDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]-2-methylidenebutyl]-trimethylsilane 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到[(3R,5aR,9aR)-2,2,5a-trimethyl-7-methylidene-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-3-yl]oxy-trimethylsilane
  参考文献：
  名称：

  Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

  摘要：

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

  DOI：

  10.1021/ja1006806
• 作为产物：
  描述：

  4-((2R,3R)-3-(2-((R)-3,3-dimethyloxiran-2-yl)ethyl)-3-methyloxiran-2-yl)but-1-en-2-yl trifluoromethanesulfonate 、 (三甲基硅基)甲基氯化镁 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以85%的产率得到[4-[(2R,3R)-3-[2-[(2R)-3,3-dimethyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]-2-methylidenebutyl]-trimethylsilane
  参考文献：
  名称：

  Biomimetic Syntheses from Squalene-Like Precursors: Synthesis of ent-Abudinol B and Reassessment of the Structure of Muzitone

  摘要：

  We achieved the stereoselective syntheses of two different structural patterns corresponding to the enantiomers of the marine natural products abudinol B and muzitone, by developing two-directional tandem biomimetic cyclizations of polyepoxides of squalene analogues in which one alkene was functionalized as an enolsilane. In the course of this work, we demonstrated that the structure of muzitone was misassigned.

  DOI：

  10.1021/ja1006806