2-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]acetaldehyde | 161658-96-4

• 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: 2-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]acetaldehyde
• CAS: 161658-96-4
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: VBXSVDSJAMFGHW-FOGDFJRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]acetaldehyde 在 镍 potassium fluoride 、 氢气 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 48.0h， 生成 (2R,3S)-3-Amino-1-((1S,2S,4R)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-butan-2-ol
  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 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到2-[(1S,2S,4R)-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]acetaldehyde
  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