N-allyl-N-(1,4-dioxaspiro<5.4>deca-7-en-8-yl)benzamide | 221216-05-3

• 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-allyl-N-(1,4-dioxaspiro<5.4>deca-7-en-8-yl)benzamide
• 英文别名: N-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-prop-2-enylbenzamide
• CAS: 221216-05-3
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: ITYRYDSYEKUSSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(1,4-dioxaspiro<5.4>deca-7-en-8-yl)benzamide 在 盐酸 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.5h， 生成 trans-5a,11b-6-allyl-1,5,5a,6,7,11b-hexahydropyrazolo<3,4-b>phenanthridine
  参考文献：
  名称：

  Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane

  摘要：

  In an analogy to the potent catechol dopamine D-1 agonists dihydrexidine (1) and dinapsoline (2), benzo rings were fused onto the structures of the dopamine D-2-selective agonists quinelorane (3) and quinpirole (4). Each of the phenyl ring-substituted derivatives had significant affinity for D-2 receptors, albeit somewhat lower than the two parent compounds, 3 and 4. Compounds with N-propyl and N-allyl substituents (5b, 5c, 6c, and 6d) had higher affinity for the D-2 dopamine receptor than did their corresponding secondary amines (5a and 6a). Slightly different effects on affinity of an n-propyl and an n-allyl group in the new analogues of 3 and 4 suggest that different binding orientations may be invoked at the receptor.

  DOI：

  10.1021/jm9804533
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 6.0h， 生成 N-allyl-N-(1,4-dioxaspiro<5.4>deca-7-en-8-yl)benzamide
  参考文献：
  名称：

  Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane

  摘要：

  In an analogy to the potent catechol dopamine D-1 agonists dihydrexidine (1) and dinapsoline (2), benzo rings were fused onto the structures of the dopamine D-2-selective agonists quinelorane (3) and quinpirole (4). Each of the phenyl ring-substituted derivatives had significant affinity for D-2 receptors, albeit somewhat lower than the two parent compounds, 3 and 4. Compounds with N-propyl and N-allyl substituents (5b, 5c, 6c, and 6d) had higher affinity for the D-2 dopamine receptor than did their corresponding secondary amines (5a and 6a). Slightly different effects on affinity of an n-propyl and an n-allyl group in the new analogues of 3 and 4 suggest that different binding orientations may be invoked at the receptor.

  DOI：

  10.1021/jm9804533