(2S)-N-methyl-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-2-methyl-5-benzyloxypentamide | 1159576-52-9

• 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)-N-methyl-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-2-methyl-5-benzyloxypentamide
• 英文别名: (2S)-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N,2-dimethyl-5-phenylmethoxypentanamide
• CAS: 1159576-52-9
• 化学式: C₂₃H₃₁NO₃
• 分子量: 369.504
• InChiKey: XYFSVISPVAWVAQ-JQVVWYNYSA-N

物化性质

• 沸点：
  527.2±50.0 °C(predicted)
• 密度：
  1.082±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-N-methyl-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-2-methyl-5-benzyloxypentamide 在 ammonia borane 、 lithium diisopropyl amide 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以81%的产率得到(2S)-5-(benzyloxy)-2-methylpentan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters

  摘要：

  The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on a stereospecific alkylation with an alcohol-protected alkyl iodide using a pseudoephedrine derivative as a chiral auxiliary followed by subsequent removal of the auxiliary. Both enantiomers are obtained in excellent yields and enantioselectivities (93-94% ee). The strategy outlined allows preparation of a wide variety of enantiopure methyl-branched saturated and unsaturated tatty acids. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.041
• 作为产物：
  描述：

  3-benzyloxypropyl iodide 、 丙酰胺,N-[(1R,2R)-2-羟基-1-甲基-2-苯基乙基]-N-甲基- 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以4.86 g的产率得到(2S)-N-methyl-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-2-methyl-5-benzyloxypentamide
  参考文献：
  名称：

  Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters

  摘要：

  The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on a stereospecific alkylation with an alcohol-protected alkyl iodide using a pseudoephedrine derivative as a chiral auxiliary followed by subsequent removal of the auxiliary. Both enantiomers are obtained in excellent yields and enantioselectivities (93-94% ee). The strategy outlined allows preparation of a wide variety of enantiopure methyl-branched saturated and unsaturated tatty acids. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.041

文献信息

• Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters
  作者：Lourdes Muñoz、Ma Pilar Bosch、Gloria Rosell、Angel Guerrero

  DOI：10.1016/j.tetasy.2009.02.041

  日期：2009.3

  The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on a stereospecific alkylation with an alcohol-protected alkyl iodide using a pseudoephedrine derivative as a chiral auxiliary followed by subsequent removal of the auxiliary. Both enantiomers are obtained in excellent yields and enantioselectivities (93-94% ee). The strategy outlined allows preparation of a wide variety of enantiopure methyl-branched saturated and unsaturated tatty acids. (c) 2009 Elsevier Ltd. All rights reserved.