2-丙酰胺-7-甲氧基-3,4-二氢萘-1-(2H)-酮 | 88058-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-丙酰胺-7-甲氧基-3,4-二氢萘-1-(2H)-酮
• 中文别名: 2-叠氮基乙基2-乙酰氨基-2-脱氧β-D-吡喃半乳糖苷
• 英文名称: 2-Propanamido-7-methoxy-3,4-dihydronaphthalen-1-(2H)-one
• 英文别名: N-(7-methoxy-1-oxo-3,4-dihydro-2H-naphthalen-2-yl)propanamide
• CAS: 88058-66-6
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: VRUWWWJHIKQWDV-UHFFFAOYSA-N

物化性质

• 熔点：
  129-131°C
• 沸点：
  486.4±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-丙酰胺-7-甲氧基-3,4-二氢萘-1-(2H)-酮 在 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 水 为溶剂， 反应 1.25h， 生成 N-[(1R,2R)-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘基]丙酰胺
  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：

  7-甲氧基-1-萘满酮 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醚 、 正丁醇 为溶剂， 反应 4.0h， 生成 2-丙酰胺-7-甲氧基-3,4-二氢萘-1-(2H)-酮
  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

• 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。
• JONES, J. H.;ANDERSON, P. S.;BALDWIN, J. J.;CLINESCHMIDT, B. V.;MCCLURE, +, J. MED. CHEM., 1985, 27, N 12, 1607-1613
  作者：JONES, J. H.、ANDERSON, P. S.、BALDWIN, J. J.、CLINESCHMIDT, B. V.、MCCLURE, +

  DOI：——

  日期：——
• 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.