(4aR,10bR)-4-ethyl-4a,5,6,10b-tetrahydrobenzo[h][1,4]benzoxazin-3-one | 92421-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (4aR,10bR)-4-ethyl-4a,5,6,10b-tetrahydrobenzo[h][1,4]benzoxazin-3-one
• CAS: 92421-92-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: RNQWMUAIGTXLHY-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aR,10bR)-4-ethyl-4a,5,6,10b-tetrahydrobenzo[h][1,4]benzoxazin-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (4aS,10bS)-4-ethyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazine
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014
• 作为产物：
  描述：

  2-hydroxyimino-3,4-dihydro-2H-1-naphthalenone 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲醚 、 乙二醇 为溶剂， 反应 3.0h， 生成 (4aR,10bR)-4-ethyl-4a,5,6,10b-tetrahydrobenzo[h][1,4]benzoxazin-3-one
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014

文献信息

• US4420480A
  申请人：——

  公开号：US4420480A

  公开（公告）日：1983-12-13
• Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists
  作者：James H. Jones、Paul S. Anderson、John J. Baldwin、Bradley V. Clineschmidt、David E. McClure、George F. Lundell、William C. Randall、Gregory E. Martin、Michael Williams

  DOI：10.1021/jm00378a014

  日期：1984.12

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.