trans-(+/-)-3,4,4a,5,6,8a-hexahydro-4-propyl-2H-1,4-benzoxazin-7(8H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: trans-(+/-)-3,4,4a,5,6,8a-hexahydro-4-propyl-2H-1,4-benzoxazin-7(8H)-one
• 英文别名: (4aR,8aR)-4-propyl-3,4a,5,6,8,8a-hexahydro-2H-benzo[b][1,4]oxazin-7-one
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: LUQGUYDFRNPZQU-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-(+/-)-3,4,4a,5,6,8a-hexahydro-4-propyl-2H-1,4-benzoxazin-7(8H)-one 在 氢溴酸 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 (4aS,8aS)-6-Bromo-4-propyl-octahydro-benzo[1,4]oxazin-7-one
  参考文献：
  名称：

  Synthesis of D-oxa tricyclic partial ergolines as dopamine agonists

  摘要：

  A series of hetero fused hexahydro-1,4-benzoxazines has been synthesized and evaluated for dopamine agonist activity. This class of compounds is another example in which an oxygen substitution in the D ring of a partial ergoline or ergoline retains dopaminergic properties. Compound 10, trans-(+/-)-4,4a,5,6,8a,9-hexahydro-5-propyl-2H,7H-pyrazolo[4,3-g] [1,4]benzoxazine, is a D-ring analogue of trans-(+/-)-4,4a,5,6,7,8,8a,9-octahydro-5-propyl-2H-pyrazolo[3,4-g]qu ino line (1, LY141865) and also a des-A-ring analogue of 9-oxaergoline. Compounds 10, 2-aminohexahydrothiazolo[1,4]benzoxazine 11, and 2-aminohexahydropyrimido[1,4]benzoxazine 12 possess dopaminergic activity in prolactin inhibition and 6-hydroxydopamine lesioned rat turning assays.

  DOI：

  10.1021/jm00386a023
• 作为产物：
  描述：

  7-Methoxy-4-propyl-3,4,5,8-tetrahydro-2H-benzo[1,4]oxazine 在 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 trans-(+/-)-3,4,4a,5,6,8a-hexahydro-4-propyl-2H-1,4-benzoxazin-7(8H)-one
  参考文献：
  名称：

  Synthesis of D-oxa tricyclic partial ergolines as dopamine agonists

  摘要：

  A series of hetero fused hexahydro-1,4-benzoxazines has been synthesized and evaluated for dopamine agonist activity. This class of compounds is another example in which an oxygen substitution in the D ring of a partial ergoline or ergoline retains dopaminergic properties. Compound 10, trans-(+/-)-4,4a,5,6,8a,9-hexahydro-5-propyl-2H,7H-pyrazolo[4,3-g] [1,4]benzoxazine, is a D-ring analogue of trans-(+/-)-4,4a,5,6,7,8,8a,9-octahydro-5-propyl-2H-pyrazolo[3,4-g]qu ino line (1, LY141865) and also a des-A-ring analogue of 9-oxaergoline. Compounds 10, 2-aminohexahydrothiazolo[1,4]benzoxazine 11, and 2-aminohexahydropyrimido[1,4]benzoxazine 12 possess dopaminergic activity in prolactin inhibition and 6-hydroxydopamine lesioned rat turning assays.

  DOI：

  10.1021/jm00386a023

文献信息

• BOOHER, R. N.;KORNFELD, E. C.
  作者：BOOHER, R. N.、KORNFELD, E. C.

  DOI：——

  日期：——
• ——
  作者：BOOHER R. N.、 KORNFELD E. C.

  DOI：——

  日期：——
• US4552956A
  申请人：——

  公开号：US4552956A

  公开（公告）日：1985-11-12
• US4587336A
  申请人：——

  公开号：US4587336A

  公开（公告）日：1986-05-06
• Synthesis of D-oxa tricyclic partial ergolines as dopamine agonists
  作者：Richard N. Booher、Edmund C. Kornfeld、E. Barry Smalstig、James A. Clemens

  DOI：10.1021/jm00386a023

  日期：1987.3

  A series of hetero fused hexahydro-1,4-benzoxazines has been synthesized and evaluated for dopamine agonist activity. This class of compounds is another example in which an oxygen substitution in the D ring of a partial ergoline or ergoline retains dopaminergic properties. Compound 10, trans-(+/-)-4,4a,5,6,8a,9-hexahydro-5-propyl-2H,7H-pyrazolo[4,3-g] [1,4]benzoxazine, is a D-ring analogue of trans-(+/-)-4,4a,5,6,7,8,8a,9-octahydro-5-propyl-2H-pyrazolo[3,4-g]qu ino line (1, LY141865) and also a des-A-ring analogue of 9-oxaergoline. Compounds 10, 2-aminohexahydrothiazolo[1,4]benzoxazine 11, and 2-aminohexahydropyrimido[1,4]benzoxazine 12 possess dopaminergic activity in prolactin inhibition and 6-hydroxydopamine lesioned rat turning assays.