(2S,4R)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide | 249745-81-1

• 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: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide
• CAS: 249745-81-1
• 化学式: C₂₀H₃₃NO₂
• 分子量: 319.488
• InChiKey: JWIFDZMBUGPYGT-NTDBWNAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide 在 四氢吡咯 、 氢氧化钾 、 正丁基锂 、 硼烷四氢呋喃络合物 、 lithium 、 一水合肼 、 三苯基膦 作用下， 以 四氯化碳 、 正己烷 、 二乙二醇 为溶剂， 反应 7.42h， 生成
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620
• 作为产物：
  描述：

  (2R)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylhexanamide 在 四氢吡咯 、 咪唑 、 正丁基锂 、 lithium aluminium deuteride 、 硼烷四氢呋喃络合物 、 碘 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 (2S,4R)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide
  参考文献：
  名称：

  Sex Pheromone of the Pine Sawfly, Macrodiprion nemoralis. Stereoselective Synthesis of the Sixteen Stereoisomers of 3,7,9-Trimethyl-2-tridecyl Acetate.

  摘要：

  The sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate (5Ac) were prepared individually, each in over 99.5% stereochemical purity. The syntheses were based on the ring opening of a pure enantiomer of cis-3,4-dimethyl-gamma-butyrolactone using a pure stereoisomer of 1-lithio-2,4-dimethyloctane, the two stereogenic centres of which were introduced with high selectivity by alkylations of the amide enolates from the appropriate enantiomers of pseudoephedrine. (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecyl acetate (SRRS-5Ac) has recently been found to be the major component of the female sex pheromone of Macrodiprion nemoralis (Hymenoptera: Diprionidae). A synthetic method for the preparation of a sixteen isomer mixture of 5Ac is also presented. This mixture has been found to be biologically active in field tests.

  DOI：

  10.3891/acta.chem.scand.53-0620