(3R,4R)-1-butyl-3-(3,4-dimethoxyphenyl)-4-methylpyrrolidine | 143883-93-6

• 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: (3R,4R)-1-butyl-3-(3,4-dimethoxyphenyl)-4-methylpyrrolidine
• CAS: 143883-93-6
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: ZDQQPZZBIAIGTL-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4R)-1-butyl-3-(3,4-dimethoxyphenyl)-4-methylpyrrolidine 在 氢溴酸 作用下， 反应 2.0h， 以56%的产率得到4-((3R,4R)-1-Butyl-4-methyl-pyrrolidin-3-yl)-benzene-1,2-diol; hydrobromide
  参考文献：
  名称：

  3-Phenylpyrrolidines: synthesis and evaluation of the in vitro binding affinity at D1 and D2 receptors

  摘要：

  A variety of 3-phenylpyrrolidines were synthesized and evaluated for their dopamine binding affinity in rat striatal tissue in vitro using [H-3] SCH 23390 and [H-3] spiperone as the D1 and D2 selective radioligands, respectively. Maximal D1 and D2 receptor binding affinity occurs with a n-pentyl group on the pyrrolidine ring nitrogen. Introduction of a trans methyl group at the 4-position of the ring decreases both D1 and D2 binding affinity. However, a cis 4-methyl group increases D1 receptor selectivity when the pyrrolidine ring is substituted with a n-propyl group. 3-Phenylpyrrolidines having a catechol nucleus exhibit greater affinity at both D1 and D2 receptors than meta-hydroxyphenyl derivatives.

  DOI：

  10.1016/0223-5234(92)90155-t
• 作为产物：
  描述：

  cis-1-(n-butyl)-3-(3,4-dihydroxyphenyl)-4-(methyl)pyrrolidine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以52%的产率得到(3R,4R)-1-butyl-3-(3,4-dimethoxyphenyl)-4-methylpyrrolidine
  参考文献：
  名称：

  3-Phenylpyrrolidines: synthesis and evaluation of the in vitro binding affinity at D1 and D2 receptors

  摘要：

  A variety of 3-phenylpyrrolidines were synthesized and evaluated for their dopamine binding affinity in rat striatal tissue in vitro using [H-3] SCH 23390 and [H-3] spiperone as the D1 and D2 selective radioligands, respectively. Maximal D1 and D2 receptor binding affinity occurs with a n-pentyl group on the pyrrolidine ring nitrogen. Introduction of a trans methyl group at the 4-position of the ring decreases both D1 and D2 binding affinity. However, a cis 4-methyl group increases D1 receptor selectivity when the pyrrolidine ring is substituted with a n-propyl group. 3-Phenylpyrrolidines having a catechol nucleus exhibit greater affinity at both D1 and D2 receptors than meta-hydroxyphenyl derivatives.

  DOI：

  10.1016/0223-5234(92)90155-t