(S)-3-Benzyloxycarbonylamino-N-[(1S,2R)-2-hydroxy-1-methyl-3-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-propyl]-succinamic acid benzyl ester | 161659-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-3-Benzyloxycarbonylamino-N-[(1S,2R)-2-hydroxy-1-methyl-3-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-propyl]-succinamic acid benzyl ester
• CAS: 161659-06-9
• 化学式: C₃₃H₄₄N₂O₆
• 分子量: 564.722
• InChiKey: AZALPYMQPKSPEV-KJQPRWQFSA-N

物化性质

• 沸点：
  736.2±60.0 °C(predicted)
• 密度：
  1.161±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxycarbonylamino-N-[(1S,2R)-2-hydroxy-1-methyl-3-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-propyl]-succinamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以95%的产率得到(3S)-3-amino-4-[[(2S,3R)-3-hydroxy-4-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]butan-2-yl]amino]-4-oxobutanoic acid
  参考文献：
  名称：

  The sweetness and stereochemistry of l-aspartyl-fenchylaminoalcohol derivatives

  摘要：

  Four fenchylaminoalcohols were derived from (+)-fenchone in five steps. They were resolved with (+)- and (-)-tartaric acid, then condensed with N-carbobenzoxy-L-aspartic acid beta-benzylester followed by hydrogenolysis to give four L-aspartyl-fenchylaminoalcohols. By the evaluation of their taste, only (2R,3R)-aminoalcohol showed potent sweetness.

  DOI：

  10.1016/0040-4039(94)85033-x
• 作为产物：
  描述：

  2-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]ethanol 在 镍 potassium fluoride 、 重铬酸吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 、 HONB 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 66.0h， 生成 (S)-3-Benzyloxycarbonylamino-N-[(1S,2R)-2-hydroxy-1-methyl-3-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-propyl]-succinamic acid benzyl ester
  参考文献：
  名称：

  The sweetness and stereochemistry of l-aspartyl-fenchylaminoalcohol derivatives

  摘要：

  Four fenchylaminoalcohols were derived from (+)-fenchone in five steps. They were resolved with (+)- and (-)-tartaric acid, then condensed with N-carbobenzoxy-L-aspartic acid beta-benzylester followed by hydrogenolysis to give four L-aspartyl-fenchylaminoalcohols. By the evaluation of their taste, only (2R,3R)-aminoalcohol showed potent sweetness.

  DOI：

  10.1016/0040-4039(94)85033-x