N-(3-chlorophenyl)-L-prolinol | 141983-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(3-chlorophenyl)-L-prolinol
• 英文别名: [(2S)-1-(3-chlorophenyl)pyrrolidin-2-yl]methanol
• CAS: 141983-18-8
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: HUNCTRKKQIPMTC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N-(3-chlorophenyl)-L-prolinol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-(3-chlorophenyl)-L-prolinyl acetate
  参考文献：
  名称：

  Studies on selective nucleophilic substitution reactions of [(cyclopentadienyl)(1,3-dichlorobenzene)M]+ PF6- complexes (M = iron, ruthenium)

  摘要：

  Reactions of [cyclopentadienyl)(1,3-dichlorobenzene)M]+PF6- complexes (M = Fe, Ru) with phenoxide nucleophiles were found to proceed with excellent selectivity under mild conditions to give products of monosubstitution. Using aminophenoxides, a preference for O-arylation was observed, while amino alcohols such as prolinol react selectively on nitrogen. Methodology for sequential selective displacement of both chlorides by different nucleophiles is reported.

  DOI：

  10.1021/jo00039a015
• 作为产物：
  描述：

  L-脯氨醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 生成 N-(3-chlorophenyl)-L-prolinol
  参考文献：
  名称：

  Studies on selective nucleophilic substitution reactions of [(cyclopentadienyl)(1,3-dichlorobenzene)M]+ PF6- complexes (M = iron, ruthenium)

  摘要：

  Reactions of [cyclopentadienyl)(1,3-dichlorobenzene)M]+PF6- complexes (M = Fe, Ru) with phenoxide nucleophiles were found to proceed with excellent selectivity under mild conditions to give products of monosubstitution. Using aminophenoxides, a preference for O-arylation was observed, while amino alcohols such as prolinol react selectively on nitrogen. Methodology for sequential selective displacement of both chlorides by different nucleophiles is reported.

  DOI：

  10.1021/jo00039a015