(+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(S)-cyclopentyl-2-pyrrolidinone | 139564-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(S)-cyclopentyl-2-pyrrolidinone
• 英文别名: (5S)-5-cyclopentyl-1-[(1R)-2-hydroxy-1-phenylethyl]pyrrolidin-2-one
• CAS: 139564-37-7
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: VMSHSMHNIJEGDB-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(S)-cyclopentyl-2-pyrrolidinone 在 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以89%的产率得到(+)-5(S)-Cyclopentyl-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：

  (-)-(3R,7aR)-3-Phenyl-5-oxo-7a-cyclopentyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 在 三乙基硅烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(+)-N-<2-(1-Hydroxy-2(R)-phenylethyl)>-5(S)-cyclopentyl-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