(R)-6-Oxo-1-(2-triisopropylsilanyloxy-ethyl)-piperidine-2-carbaldehyde | 724705-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-6-Oxo-1-(2-triisopropylsilanyloxy-ethyl)-piperidine-2-carbaldehyde
• CAS: 724705-96-8
• 化学式: C₁₇H₃₃NO₃Si
• 分子量: 327.539
• InChiKey: VGQSYDGCOPSEKV-MRXNPFEDSA-N

物化性质

• 沸点：
  406.2±40.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-6-Oxo-1-(2-triisopropylsilanyloxy-ethyl)-piperidine-2-carbaldehyde 在 dimethyl sulfide borane 、 四丁基氟化铵 、 N,N-二异丙基乙胺 、 lithium chloride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 6R-(5-cyclopropyl-3S-hydroxy-pent-1E-enyl)-1-(2-hydroxyethyl)-piperidin-2-one
  参考文献：
  名称：

  Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

  摘要：

  2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the I-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be >= 95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K-i 5-130 nM) at EP4 and subtype selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.059
• 作为产物：
  描述：

  D-2-氨基己二酸 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (R)-6-Oxo-1-(2-triisopropylsilanyloxy-ethyl)-piperidine-2-carbaldehyde
  参考文献：
  名称：

  Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

  摘要：

  2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the I-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be >= 95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K-i 5-130 nM) at EP4 and subtype selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.059