2-cyclopropyl-1-methoxy-1-phenylethane

• 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: 2-cyclopropyl-1-methoxy-1-phenylethane
• 英文别名: 2-cyclopropyl-1-phenyl-1-methoxyethane；(2-Cyclopropyl-1-methoxyethyl)benzene
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: BOYLMYFKIDGYAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 3-butenyltributylstannane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到2-cyclopropyl-1-methoxy-1-phenylethane
  参考文献：
  名称：

  Stereoselective Cyclopropylmethylation Reactions of Homoallylstannanes with Carbon Electrophiles

  摘要：

  The reactions of homoallylstannanes with acetals, aldehydes, and acyl chlorides in the presence of a Lewis acid proceeded smoothly to give the corresponding cyclopropylmethylated products. The reactions of E-3-pentenylstannane with aldehydes were stereoselective and gave the erythro products predominantly. A mechanism involving antiperiplanar attack is suggested. The stereoselectivity of the Z isomer was, however, not high. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00389-6

文献信息

• Evaluation of the Relative Magnitude of the<b><i>β</i></b>-Effect of Silicon and the<b><i>γ</i></b>-Effect of Tin by Intermolecular Competition
  作者：Masanobu Sugawara、Jun-ichi Yoshida

  DOI：10.1246/bcsj.73.1253

  日期：2000.5

  The relative magnitude of the β-effect of silicon and the γ-effect of tin was evaluated by intermolecular competition. An acetal was allowed to react with a 1 : 1 mixture of an allylsilane and a homoallylstannane in the presence of TMSOTf (trimethylsilyl trifluoromethanesulfonate); the former was found to be more reactive than does the latter, indicating that the β-silyl group activates the carbon-carbon double bond more effectively than the γ-stannyl group. This is consistent with the results of molecular-orbital calculations which indicate that the HOMO level of the allylsilane is higher than that of the homoallylstannane. The intermolecular competition between a homoallylstannane and a terminal alkene toward electrophilic reactions with an acetal have revealed that the former is more reactive than the latter. This result indicates that the stannyl group at the γ-position definitely activates the carbon-carbon double bond toward electrophiles.

  通过分子间竞争评估了硅的β效应和锡的γ效应的相对大小。一个缩醛与1:1的烯丙基硅烷和同烯丙基锡烷的混合物在TMSOTf（氟代三甲基硅基磺酸酯）存在下反应；结果表明，前者的反应性比后者更强，这表明β-硅基团比γ-锡基团更有效地激活碳-碳双键。这与分子轨道计算的结果一致，后者表明烯丙基硅烷的HOMO能级高于同烯丙基锡烷。在同烯丙基锡烷和端烯烃与缩醛的亲电反应中的分子间竞争显示，前者的反应性高于后者。这个结果表明γ位的锡基团确实能激活碳-碳双键，以便与亲电试剂反应。
• Reactions of homoallylstannanes with carbon electrophiles: stereoselective cyclopropylmethylation based on the γ-effect of tin
  作者：Masanobu Sugawara、Jun-ichi Yoshida

  DOI：10.1039/a900228f

  日期：——

  Homoallylstannanes reacted with carbon electrophiles such as acetals, acid chlorides and aldehydes in the presence of Lewis acids to give the cyclopropylmethylated products with high stereoselectivities.

  同戊基锡在路易斯酸的存在下与醛类、酸氯和醛等碳电ophile反应，生成具有高立体选择性的环丙基甲基化产物。