[(Z,1S)-4-hydroxy-3-(3-methoxyphenyl)-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]but-2-enyl] 2,2-dimethylpropanoate | 616867-17-5

• 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: [(Z,1S)-4-hydroxy-3-(3-methoxyphenyl)-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]but-2-enyl] 2,2-dimethylpropanoate
• CAS: 616867-17-5
• 化学式: C₂₆H₄₀O₄
• 分子量: 416.601
• InChiKey: YYVKKMJDFKVVIR-VVPABSIFSA-N

物化性质

• 沸点：
  525.1±50.0 °C(predicted)
• 密度：
  1.014±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(Z,1S)-4-hydroxy-3-(3-methoxyphenyl)-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]but-2-enyl] 2,2-dimethylpropanoate 在 jones reagent 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 6.42h， 生成 (E)-(S)-2-Ethyl-4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-2-(3-methoxy-phenyl)-but-3-enoic acid
  参考文献：
  名称：

  A Stereodivergent Approach to Chiral Nonracemic N-Protected α,α-Dialkylated Amino Acids

  摘要：

  Menthyl carboxaldehyde is used as a chiral auxiliary to make quaternary amino acids of either configuration via a stereodivergent approach that includes an SN2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.

  DOI：

  10.1021/ja037078a
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (Z)-(S)-4-(tert-butyl-dimethyl-silanyloxy)-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-(3-methoxy-phenyl)-but-2-enyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到[(Z,1S)-4-hydroxy-3-(3-methoxyphenyl)-1-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]but-2-enyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  A Stereodivergent Approach to Chiral Nonracemic N-Protected α,α-Dialkylated Amino Acids

  摘要：

  Menthyl carboxaldehyde is used as a chiral auxiliary to make quaternary amino acids of either configuration via a stereodivergent approach that includes an SN2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.

  DOI：

  10.1021/ja037078a

文献信息

• <i>p</i>-Menthane-3-carboxaldehyde:  A Useful Chiral Auxiliary for the Synthesis of Chiral Quaternary Carbons of High Enantiomeric Purity
  作者：Claude Spino、Cédrickx Godbout、Christian Beaulieu、Magali Harter、Topwe M. Mwene-Mbeja、Luc Boisvert

  DOI：10.1021/ja046084j

  日期：2004.10.1

  from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a alpha-chiral quaternary carbon. The flexibility, efficiency, and ease of use of the method are demonstrated in a series of examples, which include the total synthesis of (+)-cuparenone as well as a partial synthesis of (-)-cassiol.

  (+)- 或 (-)-p-Menthane-3-carboxaldehyde 分别由 (+)- 或 (-)-薄荷酮通过两个简单的步骤制成。这种助剂允许合成带有α-手性季碳的羰基化合物。该方法的灵活性、效率和易用性在一系列例子中得到了证明，其中包括 (+)-cuparenone 的全合成以及 (-)-cassiol 的部分合成。
• A Stereodivergent Approach to Chiral Nonracemic N-Protected α,α-Dialkylated Amino Acids
  作者：Claude Spino、Cédrickx Gobdout

  DOI：10.1021/ja037078a

  日期：2003.10.1

  Menthyl carboxaldehyde is used as a chiral auxiliary to make quaternary amino acids of either configuration via a stereodivergent approach that includes an SN2' displacement by a cuprate reagent and a Curtius rearrangement as key steps.