diethyl {2-[(2S)-2-(2-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}phosphonate | 928145-03-3

• 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: diethyl {2-[(2S)-2-(2-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}phosphonate
• 英文别名: 2-diethoxyphosphoryl-1-[(2S)-2-(2-hydroxyethyl)piperidin-1-yl]ethanone
• CAS: 928145-03-3
• 化学式: C₁₃H₂₆NO₅P
• 分子量: 307.327
• InChiKey: FMIDODCOSSNKDX-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl {2-[(2S)-2-(2-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}phosphonate 在 copper(l) iodide 、 sodium hydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 (2S,9aS)-octahydro-2-methyl-(4H)-quinolizin-4-one
  参考文献：
  名称：

  Total Synthesis of (−)-Senepodine G and (−)-Cermizine C

  摘要：

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).

  DOI：

  10.1021/jo062067w
• 作为产物：
  描述：

  2-哌啶乙醇 在 potassium carbonate 、 (+)-10-camphorsulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.75h， 生成 diethyl {2-[(2S)-2-(2-hydroxyethyl)piperidin-1-yl]-2-oxoethyl}phosphonate
  参考文献：
  名称：

  Total Synthesis of (−)-Senepodine G and (−)-Cermizine C

  摘要：

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).

  DOI：

  10.1021/jo062067w

文献信息

• Total Synthesis of (−)-Senepodine G and (−)-Cermizine C
  作者：Barry B. Snider、James F. Grabowski

  DOI：10.1021/jo062067w

  日期：2007.2.1

  An efficient, stereospecific synthesis of the alkaloids senepodine G (2 and cermizine C (1) has been completed using the BF3 center dot Et2O-promoted stereospecific addition of Me2CuLi to alpha,beta-unsaturated lactam 6 to provide lactam 3 the addition of MeMgBr followed by HCl to convert 3 to senepodine G (2) (six steps, 40% overall yield), and the stereospecific NaBH4 reduction of 2 to give cermizine C (1) (seven steps, 40% overall yield).