(+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidinone | 139564-36-6

• 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: (+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidinone
• 英文别名: (5R)-5-heptyl-1-[(1R)-2-hydroxy-1-phenylethyl]pyrrolidin-2-one
• CAS: 139564-36-6
• 化学式: C₁₉H₂₉NO₂
• 分子量: 303.445
• InChiKey: GEEWVWPEQSGKJJ-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidinone 在 氨 、 lithium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以93%的产率得到(+)-5(R)-n-Heptyl-2-pyrrolidinone
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones

  摘要：

  An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.

  DOI：

  10.1021/jo00032a012
• 作为产物：
  描述：

  4-氧代十一烷酸 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 13.5h， 生成 (+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(R)-heptyl-2-pyrrolidinone
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones

  摘要：

  An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.

  DOI：

  10.1021/jo00032a012