2-ethyl 3-methyl (2RS,3SR,3aSR,9bRS)-1-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicarboxylate

• 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: 2-ethyl 3-methyl (2RS,3SR,3aSR,9bRS)-1-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicarboxylate
• 英文别名: 2-ethyl-3-methyl-(2RS,3SR,3aSR,9bRS)-1-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicarboxylate；2-O-ethyl 3-O-methyl (2S,3R,3aR,9bS)-1-benzyl-3,3a,4,9b-tetrahydro-2H-chromeno[4,3-b]pyrrole-2,3-dicarboxylate
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: FJRRBGPLKFRMPQ-WLRLJWMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  顺丁烯二酸单甲酯 在 硼烷四氢呋喃络合物 、 potassium carbonate 、 三乙胺 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.75h， 生成 2-ethyl 3-methyl (2RS,3SR,3aSR,9bRS)-1-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2,3-dicarboxylate
  参考文献：
  名称：

  Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

  摘要：

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.074

文献信息

• Microwave-Assisted Solvent-Free Synthesis of Hexahydrochromeno[4,3-b]pyrroles
  作者：Jiří Pospíšil、Milan Potáček

  DOI：10.1002/ejoc.200300481

  日期：2004.2

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15 min in 80% yields. Moreover, we have observed pronounced steric requirements of alkyl substituents toward the 1,3-dipolar cycloadditions. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

  我们报告了六氢色基 [4,3-b] 吡咯的微波辅助无溶剂合成。在这些条件下，分子内 1,3-偶极环加成在 15 分钟内以 80% 的产率进行。此外，我们观察到烷基取代基对 1,3-偶极环加成有明显的空间要求。(C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004。
• Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations
  作者：Jiří Pospíšil、Milan Potáček

  DOI：10.1016/j.tet.2006.10.074

  日期：2007.1

  We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described. (c) 2006 Elsevier Ltd. All rights reserved.