5-(3,5-dimethoxyphenyl)-4-oxopentanenitrile | 165821-68-1

• 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: 5-(3,5-dimethoxyphenyl)-4-oxopentanenitrile
• 英文别名: 5-(3,4-Dimethoxyphenyl)-4-oxopentanenitrile
• CAS: 165821-68-1
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: GXZFYGUVEASINK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,5-dimethoxyphenyl)-4-oxopentanenitrile 在 dimethyl sulfide borane 、 (S)-oxazaborolidine catalyst 、 硼烷 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.42h， 生成 (R)-2-(3,4-二甲氧基苄基)-吡咯烷
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

  摘要：

  Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

  DOI：

  10.1080/00397919508012679
• 作为产物：
  描述：

  1-氰基-2-碘乙烷 、 (3,4-二甲氧基苯基)乙酰氯 在 锌 作用下， 以64%的产率得到5-(3,5-dimethoxyphenyl)-4-oxopentanenitrile
  参考文献：
  名称：

  Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

  摘要：

  Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

  DOI：

  10.1080/00397919508012679