benzyl (S)-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate | 1000313-92-7

• 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: benzyl (S)-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate
• CAS: 1000313-92-7
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: DGTOKEYZGVNADP-HXUWFJFHSA-N

物化性质

• 沸点：
  586.1±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (S)-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate 在 sodium periodate 、 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以1.62 g的产率得到benzyl (3S,2'RS)-4-[3-(2-hydroxy-3-nitropropionyloxy)-4,4-dimethyl-2-oxopyrrolidin-1-yl]benzoate
  参考文献：
  名称：

  Asymmetric Diels–Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation

  摘要：

  The main nitronorbornene adduct derived from the asymmetric Diels-Alder reaction of (S)-benzyl-4-(3-(3-nitroacryloyloxy)-4,4- dimethyl-2-oxopyrrolidin-1-yl) benzoate (S)-1 and cyclopentadiene was isolated and transformed to afford the enantiopure bicyclic beta-amino acid (1S,2R,3R,4R)-trans-beta-norbornane amino acid 9. The enantiomer (1R,2S,3S,4S)-9 could be obtained by the same synthetic route by using the chiral auxiliary (R)-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.001
• 作为产物：
  描述：

  (S)-benzyl 4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl (S)-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoate
  参考文献：
  名称：

  Asymmetric Diels–Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation

  摘要：

  The main nitronorbornene adduct derived from the asymmetric Diels-Alder reaction of (S)-benzyl-4-(3-(3-nitroacryloyloxy)-4,4- dimethyl-2-oxopyrrolidin-1-yl) benzoate (S)-1 and cyclopentadiene was isolated and transformed to afford the enantiopure bicyclic beta-amino acid (1S,2R,3R,4R)-trans-beta-norbornane amino acid 9. The enantiomer (1R,2S,3S,4S)-9 could be obtained by the same synthetic route by using the chiral auxiliary (R)-1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.001