3-allyloxymethyl-3-methylcyclopropene | 474657-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-allyloxymethyl-3-methylcyclopropene
• CAS: 474657-76-6
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: YNMHYHVVOWRVRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  9.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-allyloxymethyl-3-methylcyclopropene 、 三正丁基氢锡 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k
• 作为产物：
  描述：

  2-Brom-1-methyl-cyclopropylmethanol 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 3-allyloxymethyl-3-methylcyclopropene
  参考文献：
  名称：

  Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons

  摘要：

  The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

  DOI：

  10.1021/ja027095k