(4-acetyl-5-methyl-2-trimethylsilanylmethyl-2,3-dihydropyrrol-1-yl)phenylacetic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4-acetyl-5-methyl-2-trimethylsilanylmethyl-2,3-dihydropyrrol-1-yl)phenylacetic acid methyl ester
• 英文别名: Methyl 2-[4-acetyl-5-methyl-2-(trimethylsilylmethyl)-2,3-dihydropyrrol-1-yl]-2-phenylacetate
• 化学式: C₂₀H₂₉NO₃Si
• 分子量: 359.541
• InChiKey: ZVBCABIVOLEVGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰丙酮 在 CTAN 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 (4-acetyl-5-methyl-2-trimethylsilanylmethyl-2,3-dihydropyrrol-1-yl)phenylacetic acid methyl ester
  参考文献：
  名称：

  Solvent-Dependent Chemoselectivities in Additions of β-Carbonyl Imines to Allyltrimethylsilane with CTAN

  摘要：

  The oxidative coupling of beta-carbonyl imines and allyltrimethylsilane with CTAN were investigated in CH3CN and CH2Cl2. In CH3CN allylation products were obtained predominantly, while in CH2Cl2, dihydropyrrole products were obtained exclusively. Solvent-assisted nucleophilic cleavage of the intermediate beta-silyl cation is proposed to play a role in the solvent-dependent chemoselectivity.

  DOI：

  10.1021/jo048955d