methyl (1R,3R,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate | 130194-95-5

• 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: methyl (1R,3R,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• 英文别名: rel-Methyl (1R,3R,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
• CAS: 130194-95-5
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: PWUWUKQPSOGOPL-REBRKWNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl N-(1-phenylethyl)-α-iminoacetate 、 环戊二烯 生成 methyl (1R,3R,4S)-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
  参考文献：
  名称：

  STELLA, L.;ABRAHAM, H.;FENEAU-DUPONT, J.;TINANT, B.;DECLERCQ, J. P., TETRAHEDRON LETT., 31,(1990) N8, C. 2603-2606

  摘要：

  DOI：

文献信息

• Aza-Diels−Alder Reaction of Methyl 2-[(<i>R</i>)-1-Phenylethyl]iminoethanoate with Cyclopentadiene Using Practical and Environmentally Friendly Biphasic Solvent System
  作者：Norio Hashimoto、Hironobu Yasuda、Masaru Hayashi、Yoo Tanabe

  DOI：10.1021/op049828m

  日期：2005.1.1

  Aza-Diels-Aider reaction between 2-[(R)-1-phenylethyl]imino-ethanoate (1) and cyclopentadiene using the biphasic solvent system (TMSCI-CH3OH/toluene) gave (1S,3S,4R)-2[(R)-1-phenylethyl]-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylates (3a) in 32% isolated yield. The present method is advantageous for the large-scale synthesis, because (i) the reported methods required harmful and expensive fluorinated chemicals, (ii) methyl analogue 3a was practically isolated as a crystalline solid, and (iii) the reaction was conducted with very little observable exotherm. In addition, the absolute configurations of the other three diastereomers 2, 4, and 5 were unambiguously determined.