(2S,3R)-3-Allyloxy-2-methyl-dodecanoic acid | 460352-63-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-3-Allyloxy-2-methyl-dodecanoic acid
• 英文别名: (2S,3R)-2-methyl-3-prop-2-enoxydodecanoic acid
• CAS: 460352-63-0
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: BNTDZGQIHKFESV-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Allyloxy-2-methyl-dodecanoic acid 在 palladium on activated charcoal 叠氮磷酸二苯酯 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2R,3S,6S,7R)-3,6-Dimethyl-2,7-dinonyl-1,8-dioxa-4-aza-cyclododecan-5-one
  参考文献：
  名称：

  Synthesis of Cyclic Peptidomimetics from Aldol Building Blocks

  摘要：

  Aldol products (3-hydroxy acids) with an allylprotected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.

  DOI：

  10.1021/jo025889b
• 作为产物：
  描述：

  (4S)-4-benzyl-3-[(2S,3R)-2-methyl-3-prop-2-enoxydodecanoyl]-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2S,3R)-3-Allyloxy-2-methyl-dodecanoic acid
  参考文献：
  名称：

  Synthesis of Cyclic Peptidomimetics from Aldol Building Blocks

  摘要：

  Aldol products (3-hydroxy acids) with an allylprotected hydroxy group were converted to amino alcohols by Curtius rearrangement. Combination of the carboxylic acid with the amino alcohols gave the amides 10. Ring-closing metathesis led to the 12-membered lactams 12 as mixtures of E/Z-isomers. The scheme was also transferred to the solid-phase. In this case the macrolactams are formed via cyclorelease. For a pair of E/Z-isomers the solution conformation was determined by ROESY spectroscopy.

  DOI：

  10.1021/jo025889b