(-)-trans-1a,2,4,4a,5,6-hexahydro-9-methoxy-4-propylnaphth<1,2-b>-1,4-oxazin-3-one | 88058-74-6

• 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: (-)-trans-1a,2,4,4a,5,6-hexahydro-9-methoxy-4-propylnaphth<1,2-b>-1,4-oxazin-3-one
• 英文别名: (-)-trans-1a,2,4,4a,5,6-hexahydro-9-methoxy-4-propylnaphth[1,2-b]-1,4-oxazin-3-one；(4aR,10bR)-9-methoxy-4-propyl-4a,5,6,10b-tetrahydrobenzo[h][1,4]benzoxazin-3-one
• CAS: 88058-74-6
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: VNHUJYLFWSYPMY-GDBMZVCRSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷、DMSO、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (-)-trans-1a,2,4,4a,5,6-hexahydro-9-methoxy-4-propylnaphth<1,2-b>-1,4-oxazin-3-one 生成 (+)-trans-3,4,4a,5,6,10b-hexahydro-9-methoxy-4-propyl-2H-naphth<1,2-b>-1,4-oxazine hydrochloride
  参考文献：
  名称：

  MELILLO, DAVID G.;MATHRE, DAVID J.;LARSEN, ROBERT D.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醚 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 三氯化铝 、 草酰氯 、 dimethyl sulfide borane 、 四丁基氯化铵 、 氢气 、 四氯化钛 、 sodium carbonate 、 红铝 、 sodium chloride 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 62.92h， 生成 (-)-trans-1a,2,4,4a,5,6-hexahydro-9-methoxy-4-propylnaphth<1,2-b>-1,4-oxazin-3-one
  参考文献：
  名称：

  Practical enantioselective synthesis of a homotyrosine derivative and (R,R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist

  摘要：

  DOI：

  10.1021/jo00232a016

文献信息

• Hexahydronaphth[1,2-b]-1,4-oxazines
  申请人：Merck & Co., Inc.

  公开号：US04420480A1

  公开（公告）日：1983-12-13

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display .alpha..sub.2 -adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamidotetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁唑具有多巴胺能活性，并表现出.alpha..sub.2-肾上腺素受体拮抗作用。它们在帕金森病、抑郁症和高血压的治疗中很有用。一种重要的制备方法是通过环合成适当的2-氯乙酰胺四氢萘酚-1-醇，并还原所得的环状酰胺羰基团。
• Hexahydronaphth(1,2-b)-1,4-oxazines, process for their preparation and pharmaceutical formulation containing them
  申请人：Merck & Co., Inc.

  公开号：EP0080115A2

  公开（公告）日：1983-06-01

  Hexahydronaphth[1,2-b]-1,4-oxazines have dopaminergic activity and display α2-adrenergic receptor antagonism. They are useful in the treatment of parkinsonism, depression and hypertension. An important method of preparation is by ring closure of the appropriate 2-chloroacetamido- tetrahydronaphthalen-1-ol and reduction of the resulting cyclic amide carbonyl group.

  六氢萘并[1,2-b]-1,4-噁嗪具有多巴胺能活性，并显示出α2-肾上腺素能受体拮抗作用。 它们可用于治疗帕金森病、抑郁症和高血压。 一种重要的制备方法是将适当的 2-氯乙酰胺基四氢萘-1-醇闭环，并还原由此产生的环状酰胺羰基。
• 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.
• MELILLO, DAVID G.;MATHRE, DAVID J.;LARSEN, ROBERT D.
  作者：MELILLO, DAVID G.、MATHRE, DAVID J.、LARSEN, ROBERT D.

  DOI：——

  日期：——
• IMAGING LIGANDS
  申请人：Hegde Ravi

  公开号：US20110217234A1

  公开（公告）日：2011-09-08

  Naphthoxazine derivatives which are selective ligands for the dopamine D2 receptor and which carry an 18F radio-label suitable for imaging with PET are described. The compounds of the present invention are thus useful for in vivo diagnostics and in vivo imaging of the dopamine D2 receptor.