6-O-benzyl 1-O-ethyl (E,4S)-4-[benzyl-[(E)-4-oxo-4-phenylbut-2-enoyl]amino]hex-2-enedioate | 497830-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-benzyl 1-O-ethyl (E,4S)-4-[benzyl-[(E)-4-oxo-4-phenylbut-2-enoyl]amino]hex-2-enedioate
• CAS: 497830-84-9
• 化学式: C₃₂H₃₁NO₆
• 分子量: 525.601
• InChiKey: WIPICAAQEZYUSV-PNCVHCMPSA-N

物化性质

• 沸点：
  698.4±55.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-benzyl 1-O-ethyl (E,4S)-4-[benzyl-[(E)-4-oxo-4-phenylbut-2-enoyl]amino]hex-2-enedioate 以 苯 为溶剂， 反应 7.0h， 以49%的产率得到(3S,3aR,4S,7aS)-2-benzyl-3-benzyloxycarbonylmethyl-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
• 作为产物：
  描述：

  N-Boc-L-aspartic aldehyde β-benzyl ester 在 N-羟基-7-氮杂苯并三氮唑 、 potassium tert-butylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 6-O-benzyl 1-O-ethyl (E,4S)-4-[benzyl-[(E)-4-oxo-4-phenylbut-2-enoyl]amino]hex-2-enedioate
  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