trimethyl-[(1S,2R)-2-methyl-2-phenylcyclopropyl]stannane | 474657-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trimethyl-[(1S,2R)-2-methyl-2-phenylcyclopropyl]stannane
• CAS: 474657-85-7；959794-69-5
• 化学式: C₁₃H₂₀Sn
• 分子量: 295.012
• InChiKey: ZXAXFYOIRMOXMY-USOZLSCGSA-N

物化性质

• 沸点：
  281.1±43.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-methyl-3-phenylcyclopropene 、 三甲基锡 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到trimethyl-[(1S,2R)-2-methyl-2-phenylcyclopropyl]stannane
  参考文献：
  名称：

  Catalytic Enantioselective Hydrostannation of Cyclopropenes

  摘要：

  The first examples of catalytic enantioselective hydrostannation of the C=C double bond of cyclopropenes has been demonstrated. This method allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors. A variety of functional groups at C-3 of the cyclopropenes were tolerated.

  DOI：

  10.1021/ja0496928

文献信息

• Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes:  Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons
  作者：Marina Rubina、Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/ja027095k

  日期：2002.10.1

  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.