N-[(1R,2R)-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘基]丙酰胺 | 88058-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: N-[(1R,2R)-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘基]丙酰胺
• 中文别名: N-[（1R，2R）-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘]丙酰胺；3-(3-吡啶基)丙烯酸乙酯
• 英文名称: N-<(1R,2R)-1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl>propanamide
• 英文别名: (+)-trans-2-propionamido-7-methoxuy-1,2,3,4-tetrahydronaphthalen-1-ol；trans-2-propionamido-7-methoxy-1,2,3,4-tetrahydro-1-naphthalenol；N-[(1R,2R)-1,2,3,4-Tetrahydro-1-hydroxy-7-methoxy-2-naphthalenyl]propanamide；N-[(1R,2R)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]propanamide
• CAS: 88058-70-2
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: AGSZGRLOKYZJMA-TZMCWYRMSA-N

物化性质

• 熔点：
  158-160°C
• 沸点：
  486.1±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)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(1R,2R)-1,2,3,4-四氢-1-羟基-7-甲氧基-2-萘基]丙酰胺 在 lithium aluminium tetrahydride 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醚 、 乙二醇 为溶剂， 反应 4.0h， 生成 (+)-trans-3,4,4a,5,6,10b-hexahydro-9-methoxy-4-propyl-2H-naphth<1,2-b>-1,4-oxazine
  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-氯苯甲醚 在 palladium on activated charcoal 氢氧化钾 、 三氯化铝 、 草酰氯 、 氢气 、 四氯化钛 、 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 57.92h， 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：

  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, 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.
• JONES, J. H.
  作者：JONES, J. H.

  DOI：——

  日期：——
• 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：——
• MELILLO, DAVID G.;LARSEN, ROBERT D.;MATHRE, DAVID J.;SHUKIS, WILLIAM F.;W+, J. ORG. CHEM., 52,(1987) N 23, 5143-5150
  作者：MELILLO, DAVID G.、LARSEN, ROBERT D.、MATHRE, DAVID J.、SHUKIS, WILLIAM F.、W+

  DOI：——

  日期：——