3-[1-(methoxymethoxy)-1-methylethyl]-3-methylcyclopropene | 682760-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[1-(methoxymethoxy)-1-methylethyl]-3-methylcyclopropene
• 英文别名: 3-[2-(methoxymethoxy)propan-2-yl]-3-methylcyclopropene
• CAS: 682760-61-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: RLLGIVKODJHIQR-UHFFFAOYSA-N

物化性质

• 沸点：
  154.9±13.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  三甲基锡 、 3-[1-(methoxymethoxy)-1-methylethyl]-3-methylcyclopropene 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到[(1S,2R)-2-[2-(methoxymethoxy)propan-2-yl]-2-methylcyclopropyl]-trimethylstannane
  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
• 作为产物：
  描述：

  methyl 2-bromo-1-methylcyclopropanecarboxylate 在 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 3-[1-(methoxymethoxy)-1-methylethyl]-3-methylcyclopropene
  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

• Highly Diastereo- and Regioselective Transition Metal-Catalyzed Additions of Metal Hydrides and Bimetallic Species to Cyclopropenes:  Easy Access to Multisubstituted Cyclopropanes
  作者：Alexander Trofimov、Marina Rubina、Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/jo701855c

  日期：2007.11.1

  The first highly efficient, diastereo- and regioselective transition metal-catalyzed addition of metal hydrides (stannanes, silanes, and germanes) and bimetallic species (ditins and silyltins) to cyclopropenes has been developed. It was shown that the addition across the double bond of cyclopropenes is generally controlled by steric factors and proceeds from the least hindered face. This methodology

  已经开发出第一种高效的，非对映的和区域选择性的过渡金属催化的金属氢化物（锡烷，硅烷和锗烷）和双金属物质（二锡和甲硅烷基锡）添加到环丙烯中。结果表明，环丙烯双键的加成通常受空间因素控制，并且从受阻最小的面开始。这种方法论代表了一种针对各种高度取代的立体定义的环丙基金属的有力且原子经济的方法，而其他方法则无法提供有用的构建基块。