(-)-PHNO | 88058-89-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (-)-PHNO
• 英文别名: N 0500；(4aS,10bS)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazin-9-ol
• CAS: 88058-89-3
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: JCSREICEMHWFAY-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4aS,10bS)-9-Methoxy-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine; hydrochloride 在 吡啶盐酸盐 作用下， 以65%的产率得到(-)-PHNO
  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

• A novel and efficient method for the conversion of a trans-hexahydronaphthoxazine to a cis-isomer using boron tribromide
  作者：Francis A.J. Kerdesky

  DOI：10.1016/j.tetlet.2005.01.048

  日期：2005.3

  A novel and efficient method for the conversion of a trans-hexahydronaplithoxazine to a cis-isomer was achieved in high yield by utilizing boron tribromide in methylene chloride at -20 degreesC. (C) 2005 Published by Elsevier Ltd.
• US6025356A
  申请人：——

  公开号：US6025356A

  公开（公告）日：2000-02-15
• 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.