(3S,3aR,4S,7aR)-2-benzyl-3-isopropyl-1-oxo-6-phenyl-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester | 497832-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (3S,3aR,4S,7aR)-2-benzyl-3-isopropyl-1-oxo-6-phenyl-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester
• 英文别名: ethyl (3S,3aR,4S,7aR)-2-benzyl-1-oxo-6-phenyl-3-propan-2-yl-3,3a,4,7a-tetrahydropyrano[3,4-c]pyrrole-4-carboxylate
• CAS: 497832-80-1
• 化学式: C₂₆H₂₉NO₄
• 分子量: 419.521
• InChiKey: QJNSNWOUGKBDAK-IGABQKFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,3aR,4S,7aR)-2-benzyl-3-isopropyl-1-oxo-6-phenyl-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester 在 水 作用下， 以 甲苯 为溶剂， 以83%的产率得到(S)-[(2S,3R,4S)-1-Benzyl-2-isopropyl-5-oxo-4-(2-oxo-2-phenyl-ethyl)-pyrrolidin-3-yl]-hydroxy-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

  摘要：

  Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a-j undergo facile stereoselective intramolecular Diels-Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a-j. These reactions allow for directed remote hydroxylation with complete control of stereochemistry. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01711-2
• 作为产物：
  描述：

  (E)-(S)-4-Amino-5-methyl-hex-2-enoic acid ethyl ester 在 N-羟基-7-氮杂苯并三氮唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 (3S,3aR,4S,7aR)-2-benzyl-3-isopropyl-1-oxo-6-phenyl-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  An intramolecular oxo Diels–Alder approach to 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters

  摘要：

  The diastereoselective synthesis of a series of 1-oxo-1,2,3,3a,4,7a-hexahydro-pyrano[3,4-c]pyrrole-4-carboxylic acid ethyl esters via an oxo Diels-Alder reaction is described. Ab initio calculations predicted the products of the exo cycloaddition to be the thermodynamic products while the products resulting from the endo cycloaddition were predicted to be the kinetic products. The calculations were born out by experimental data. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.04.007