3-methoxymethyl-3-methylcyclopropene | 474657-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxymethyl-3-methylcyclopropene
• 英文别名: 3-(Methoxymethyl)-3-methylcyclopropene；3-(methoxymethyl)-3-methylcyclopropene
• CAS: 474657-75-5
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: CMLNURHMMFFSSH-UHFFFAOYSA-N

物化性质

• 沸点：
  75.4±9.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methoxymethyl-3-methylcyclopropene 在 盐酸 、 sodium periodate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,2-二[(2R,5R)-2,5-二异丙基磷杂环戊烷基]乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 ((1S,2R)-2-(Methoxymethyl)-2-methylcyclopropyl)boronic acid
  参考文献：
  名称：

  环丙烯的催化对映选择性硼氢化反应

  摘要：

  已经通过铑催化的 3,3-二取代环丙烯的不对称硼氢化反应合成了具有高度非对映选择性和对映选择性的 2,2-二取代环丙基硼酸酯。酯和烷氧基甲基取代基的强导向作用已被证明。发现定向效应对于实现高度的对映体诱导是必要的。选定的环丙基硼衍生物成功地用于 Suzuki 交叉偶联反应，以良好的产率生产相应的旋光芳基和乙烯基环丙烷。

  DOI：

  10.1021/ja034210y
• 作为产物：
  描述：

  methyl 2-bromo-1-methylcyclopropanecarboxylate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 3-methoxymethyl-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

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.
• Catalytic Enantioselective Hydroboration of Cyclopropenes
  作者：Marina Rubina、Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/ja034210y

  日期：2003.6.1

  2,2-Disubstituted cyclopropyl boronates have been synthesized with high degrees of diastereo- and enantioselectivity via the rhodium-catalyzed asymmetric hydroboration of 3,3-disubstituted cyclopropenes. A strong directing effect of ester and alkoxymethyl substituents has been demonstrated. The directing effect was found to be necessary in achieving high degrees of enantiomeric induction. Selected

  已经通过铑催化的 3,3-二取代环丙烯的不对称硼氢化反应合成了具有高度非对映选择性和对映选择性的 2,2-二取代环丙基硼酸酯。酯和烷氧基甲基取代基的强导向作用已被证明。发现定向效应对于实现高度的对映体诱导是必要的。选定的环丙基硼衍生物成功地用于 Suzuki 交叉偶联反应，以良好的产率生产相应的旋光芳基和乙烯基环丙烷。