(1R^*,2S^*,3S^*)-N,N-Diethyl-2-hydroxy-3-(2-hydroxy-2-methylpropyl)-2-methylcyclopentanamide | 132103-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R^*,2S^*,3S^*)-N,N-Diethyl-2-hydroxy-3-(2-hydroxy-2-methylpropyl)-2-methylcyclopentanamide
• 英文别名: (1S,2R,3R)-N,N-diethyl-2-hydroxy-3-(2-hydroxy-2-methylpropyl)-2-methylcyclopentane-1-carboxamide
• CAS: 132103-10-7
• 化学式: C₁₅H₂₉NO₃
• 分子量: 271.4
• InChiKey: YZTYAWZQPIUXQW-LALPHHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-Diethyl-2-acetyl-5-hexenamide 、 丙酮 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以46%的产率得到(1R^*,2S^*,3S^*)-N,N-Diethyl-2-hydroxy-3-(2-hydroxy-2-methylpropyl)-2-methylcyclopentanamide
  参考文献：
  名称：

  Sequential radical cyclization/intermolecular carbonyl addition reactions initiated by samarium(II) iodide

  摘要：

  A sequential reductive coupling process promoted by samarium (II) iodide (SmI2) is described. Thus, ethyl 2-acetyl-2-methyl-5-hexenoate, upon treatment with SmI2 in the presence of a variety of aldehydes or ketones, undergoes an initial radical (ketyl) olefin cyclization. Subsequent reduction of the intermediate radical generated in this process produces a transient organosamarium species which can be trapped in situ by the added aldehyde or ketone electrophiles. Through this sequential radical cyclization/intermolecular carbonyl addition reaction, two new carbon-carbon bonds are generated in a one-pot process. Furthermore, a high degree of stereochemical control is established over three contiguous stereocenters, markedly increasing molecular complexity from the starting materials to the observed products.

  DOI：

  10.1021/jo00004a020