[(3S,4S)-4-methyl-5-oxoheptan-3-yl] N-[(1S)-1-phenylethyl]carbamate | 212318-67-7

• 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: [(3S,4S)-4-methyl-5-oxoheptan-3-yl] N-[(1S)-1-phenylethyl]carbamate
• CAS: 212318-67-7
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: XPYAAPNGPGABLL-WWGRRREGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(3S,4S)-4-methyl-5-oxoheptan-3-yl] N-[(1S)-1-phenylethyl]carbamate 在 三氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (4S,5S)-(+)-4-methyl 5-hydroxy heptan 3-one
  参考文献：
  名称：

  A Versatile Approach Towards Enantiopure α-Methyl β-Hydroxy Ketones. Application to the Synthesis of (4R,5S) Sitophilure and of Its Stereoisomers

  摘要：

  Rice weevil pheromone sitophilure ((4R,5S)-5-hydroxy-4-methyl-3-heptanone) and its three diastereomers were synthesized in three steps, starting from 3-(trimethylsilyloxy)-1,3-pentadiene and propionaldehyde. Other optically active alpha-methyl beta-hydroxy ketones can also be synthesized by the reported procedure.

  DOI：

  10.1080/00397919808004830
• 作为产物：
  描述：

  3-trimethylsiloxypenta-1,3-diene 在 bis(cyclopentadienyl)titanium (III) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 31.75h， 生成 [(3S,4S)-4-methyl-5-oxoheptan-3-yl] N-[(1S)-1-phenylethyl]carbamate
  参考文献：
  名称：

  A Versatile Approach Towards Enantiopure α-Methyl β-Hydroxy Ketones. Application to the Synthesis of (4R,5S) Sitophilure and of Its Stereoisomers

  摘要：

  Rice weevil pheromone sitophilure ((4R,5S)-5-hydroxy-4-methyl-3-heptanone) and its three diastereomers were synthesized in three steps, starting from 3-(trimethylsilyloxy)-1,3-pentadiene and propionaldehyde. Other optically active alpha-methyl beta-hydroxy ketones can also be synthesized by the reported procedure.

  DOI：

  10.1080/00397919808004830