syn-5-Carbomethoxy-5-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>-4,5-dihydroisoxazole

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: syn-5-Carbomethoxy-5-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>-4,5-dihydroisoxazole
• 英文别名: methyl (5S)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-phenyl-4H-1,2-oxazole-5-carboxylate
• 化学式: C₁₉H₂₉NO₄Si
• 分子量: 363.529
• InChiKey: ASABRIBUMMTURC-KUHUBIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-2-亚甲基丁酸甲酯 在 咪唑 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 syn-5-Carbomethoxy-5-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>-4,5-dihydroisoxazole
  参考文献：
  名称：

  1,3-Dipolar Cycloadditions to Baylis-Hillman Adducts: Rationale for the Observed Diastereoselectivity

  摘要：

  Diazomethane and benzonitrile oxide cycloadditions were performed on Baylis-Hillman adducts derived from methyl acrylate and aldehydes (beta'-alkoxy-alpha,beta-unsaturated esters). The reactions proceed in good chemical yields, and their stereochemical outcome can be explained by the ''inside alkoxy effect'' theory. In the case of diazomethane cycloadditions, however, electrostatic factors play a reduced role in comparison to the corresponding nitrile oxide reactions, while steric effects are of major importance in governing the stereoselectivity. This different behavior of the two 1,3-dipoles finds a rationale in the analysis of the atomic charges as calculated at the RHF/3-21G level of theory for the transition structure of these reactions.

  DOI：

  10.1021/jo00120a009

文献信息

• 1,3-Dipolar Cycloadditions to Baylis-Hillman Adducts: Rationale for the Observed Diastereoselectivity
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1021/jo00120a009

  日期：1995.7

  Diazomethane and benzonitrile oxide cycloadditions were performed on Baylis-Hillman adducts derived from methyl acrylate and aldehydes (beta'-alkoxy-alpha,beta-unsaturated esters). The reactions proceed in good chemical yields, and their stereochemical outcome can be explained by the ''inside alkoxy effect'' theory. In the case of diazomethane cycloadditions, however, electrostatic factors play a reduced role in comparison to the corresponding nitrile oxide reactions, while steric effects are of major importance in governing the stereoselectivity. This different behavior of the two 1,3-dipoles finds a rationale in the analysis of the atomic charges as calculated at the RHF/3-21G level of theory for the transition structure of these reactions.