[3-(Methoxymethoxymethyl)-3-(4-methylphenyl)cyclopropen-1-yl]methanol | 1000702-80-6

• 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: [3-(Methoxymethoxymethyl)-3-(4-methylphenyl)cyclopropen-1-yl]methanol
• CAS: 1000702-80-6
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: JUTSFJAWRZLTLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-(Methoxymethoxymethyl)-3-(4-methylphenyl)cyclopropen-1-yl]methanol 、 双二异丙基氨基氯化磷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Remarkable Stereoelectronic Control in the Lewis Base Assisted [2,3]-Rearrangement of Cyclopropenylmethyl Phosphinites

  摘要：

  A novel 2,3-rearrangement of cyclopropenylmethyl phosphinites to methylenecyclopropylphosphine oxides was demonstrated. It was found that, in striking contrast to the analogous rearrangement known for nonstrained allylic systems, this reaction does not proceed at all upon thermal activation; however, it can be efficiently mediated by Lewis bases. Unique stereoelectronic effects control the diastereoselectivity of this transformation, leading to predominant formation of the more sterically hindered products.

  DOI：

  10.1021/ol702473s
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以720 mg的产率得到[3-(Methoxymethoxymethyl)-3-(4-methylphenyl)cyclopropen-1-yl]methanol
  参考文献：
  名称：

  Remarkable Stereoelectronic Control in the Lewis Base Assisted [2,3]-Rearrangement of Cyclopropenylmethyl Phosphinites

  摘要：

  A novel 2,3-rearrangement of cyclopropenylmethyl phosphinites to methylenecyclopropylphosphine oxides was demonstrated. It was found that, in striking contrast to the analogous rearrangement known for nonstrained allylic systems, this reaction does not proceed at all upon thermal activation; however, it can be efficiently mediated by Lewis bases. Unique stereoelectronic effects control the diastereoselectivity of this transformation, leading to predominant formation of the more sterically hindered products.

  DOI：

  10.1021/ol702473s

文献信息

• Remarkable Stereoelectronic Control in the Lewis Base Assisted [2,3]-Rearrangement of Cyclopropenylmethyl Phosphinites
  作者：Marina Rubina、Eric W. Woodward、Michael Rubin

  DOI：10.1021/ol702473s

  日期：2007.12.1

  A novel 2,3-rearrangement of cyclopropenylmethyl phosphinites to methylenecyclopropylphosphine oxides was demonstrated. It was found that, in striking contrast to the analogous rearrangement known for nonstrained allylic systems, this reaction does not proceed at all upon thermal activation; however, it can be efficiently mediated by Lewis bases. Unique stereoelectronic effects control the diastereoselectivity of this transformation, leading to predominant formation of the more sterically hindered products.