2-acetamido-5-methoxy-1,2,3,4-tetrahydronaphthalene | 134865-81-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-acetamido-5-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 5-methoxy-2-acetamido-tetralin；5-Methoxy-2-acetamido tetralin；N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide
• CAS: 134865-81-9；153811-23-5；153811-37-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: HVKVUHPYXTYWNH-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-acetamido-5-methoxy-1,2,3,4-tetrahydronaphthalene 在 盐酸 作用下， 反应 18.0h， 以86%的产率得到5-甲氧基-2-四氢萘胺
  参考文献：
  名称：

  构象限制和构象定义的酪胺类似物是苯乙醇胺N-甲基转移酶的抑制剂。

  摘要：

  在寻找肾上腺素合成酶苯基乙醇胺N-甲基转移酶（PNMT; EC 2.1.1.28）的选择性抑制剂，酚2-氨基四氢化萘（酪胺的构象受限类似物为12-15）和酚苯并双环[3.2.1]辛胺（使用22-24作为酪胺的构象定义类似物）来获得有关天然底物去甲肾上腺素在PNMT活性位点上的儿茶酚羟基的结合相互作用的信息。另外，这些类似物提供了有关构象柔性对酚性苯基乙胺中氨基乙基侧链的活性位相互作用的影响的信息，这可能有助于学习去甲肾上腺素在PNMT活性位点结合的方式。类似物22-24通过九步序列合成，其中，Friedel-Crafts型分子内环化是苯并双环[3.2.1]辛烷骨架构建的关键步骤。对-酪胺（10，Ki = 294 microM）比苯乙胺（1，Ki = 854 microM）更有效，但间-酪胺（9，Ki = 1250 microM）比苯基乙胺（作为PNMT抑制剂）的效力更弱。同样，在构象受限和

  DOI：

  10.1021/jm00122a032
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 盐酸 、 sodium hydroxide 、 diborane(6) 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.25h， 生成 2-acetamido-5-methoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  .alpha.-Adrenergic agents. 2. Synthesis and .alpha.1-agonist activity of 2-aminotetralins

  摘要：

  Substituted 2-aminotetralins are potent, selective, direct-acting agonists at postjunctional alpha 1 receptors. Within this series, substituent alterations on the ring, as well as on the nitrogen, change the potency of compounds by over three orders of magnitude (EC50 = 12 to greater than 10 000 nM). It has been demonstrated experimentally that substitution at both the 5 and 8 positions of the aromatic ring produces optimum agonist potency. Removal of either substituent results in a loss of potency and efficacy relative to norepinephrine. Substitution at positions 6 and/or 7 is generally detrimental to activity. Methyl, ethyl, or dimethyl substitution on nitrogen is compatible with high agonist potency, while substitution with larger groups is not. The most potent agonist in this series is 5-(thiomethyl)-8-methoxy-2-aminotetralin, which has an EC50 of 12 nM.

  DOI：

  10.1021/jm00344a009

文献信息

• [EN] TRANSITION METAL PHOSPHINO-OXAZOLINE CATALYSTS, PROCESSES FOR THEIR PRODUCTION, AND USES THEREOF IN THE HYDROGENATION OF CYCLIC ENAMIDES AND IMINES<br/>[FR] CATALYSEURS PHOSPHINO-OXAZOLINE À BASE DE MÉTAL DE TRANSITION, LEURS PROCÉDÉS DE PRODUCTION, ET LEURS UTILISATIONS DANS L'HYDROGÉNATION D'ÉNAMIDES ET D'IMINES CYCLIQUES
  申请人：FUNDACIÓ INST DE RECERCA BIOMÈDICA (IRB BARCELONA)

  公开号：WO2016203005A1

  公开（公告）日：2016-12-22

  The present invention relates to a complex of the Formula 2, and a compound of Formula 1, and the use of said compound of Formula 1 for the synthesis of said complex of Formula 2, processes for synthesis of said compound of Formula 1, and use of said complex of Formula 2 in asymmetric hydrogenation of cyclic enamides and imines

  本发明涉及公式2的复合物，公式1的化合物以及公式1的化合物用于合成公式2的用途，公式1的化合物的合成过程，以及公式2的复合物在环烯酰胺和亚胺的不对称氢化中的应用。
• Substituted 2-amidotetralins as melatonin agonists and antagonists
  申请人：Northwestern University

  公开号：US05151446A1

  公开（公告）日：1992-09-29

  The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.

  本发明涉及具有褪黑激素受体活性的化合物，特别是取代的2-氨基四氢萘衍生物；包括含有这种化合物的药物制剂；以及使用这些化合物作为治疗和诊断试剂的方法。
• 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents
  作者：Swier Copinga、Pieter G. Tepper、Cor J. Grol、Alan S. Horn、Margarita L. Dubocovich

  DOI：10.1021/jm00072a008

  日期：1993.10

  A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to compete for 2-[I-125]iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of [H-3]dopamine from rabbit retina. The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (K(i) = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor. The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows. First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor. We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.
• Selditz; Copinga; Grol, Pharmazie, 1999, vol. 54, # 3, p. 183 - 191
  作者：Selditz、Copinga、Grol、Franke、De Zeeuw、Wikstroem、Gyllenhaal

  DOI：——

  日期：——
• US5071875A
  申请人：——

  公开号：US5071875A

  公开（公告）日：1991-12-10