tert-Butyl-(2,2-dimethyl-3-oxiranyl-propoxy)-dimethyl-silane | 866044-02-2

• 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: tert-Butyl-(2,2-dimethyl-3-oxiranyl-propoxy)-dimethyl-silane
• 英文别名: Tert-butyl-[2,2-dimethyl-3-(oxiran-2-yl)propoxy]-dimethylsilane；tert-butyl-[2,2-dimethyl-3-(oxiran-2-yl)propoxy]-dimethylsilane
• CAS: 866044-02-2
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: YSTSTIOYBZEDFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-Butyl-(2,2-dimethyl-3-oxiranyl-propoxy)-dimethyl-silane 在 碘苯二乙酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 甲基锂 、 碘 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (Z)-8-Hydroxy-10,10-dimethyl-oxacycloundec-5-en-2-one
  参考文献：
  名称：

  New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J

  摘要：

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.

  DOI：

  10.1021/ol051854x
• 作为产物：
  描述：

  2,2-二甲基-4-戊烯醛 在 咪唑 、 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 tert-Butyl-(2,2-dimethyl-3-oxiranyl-propoxy)-dimethyl-silane
  参考文献：
  名称：

  New Silicon-Mediated, Sequential Ring Expansions of n-Sized 2-Cycloalkenones into Hydroxyolefinic n + m + p Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J

  摘要：

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.

  DOI：

  10.1021/ol051854x

文献信息

• New Silicon-Mediated, Sequential Ring Expansions of <i>n</i>-Sized 2-Cycloalkenones into Hydroxyolefinic <i>n</i> + <i>m</i> + <i>p</i> Medium-Sized Lactones:  Short Synthesis of (−)-Phoracantholide-J
  作者：Gary H. Posner、Mark A. Hatcher、William A. Maio

  DOI：10.1021/ol051854x

  日期：2005.9.1

  In only four steps from 2-cyclopentenone and 2-cyclohexenone, sequential three- or four-atom and then one- to three-atom ring enlargements produce nine- to 12-membered hydroxyolefinic lactones on a gram scale. 2-Cyclopentenone undergoes this serial 5 + 3 + 2 process to form 10-membered ring natural (-)-phoracantholide-J in six linear steps and 26% overall yield.