(R)-(+)-2-(N-benzylamino)-5-methoxytetralin | 58349-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-(+)-2-(N-benzylamino)-5-methoxytetralin
• 英文别名: (+)-(2R)-2-(benzylamino)-5-methoxytetralin；N-Benzyl-N-[(2R)-5-methoxy-1, 2,3,4-tetrahydronaphthalen-2-yl]amine；N-Benzyl-N-[(2R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl]amine；Benzyl-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine；(2R)-N-benzyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 58349-20-5
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: OZFLGQHJVWSALN-MRXNPFEDSA-N

物化性质

• 沸点：
  424.4±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-(N-benzylamino)-5-methoxytetralin 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 30.0h， 生成 (2R)-1,2,3,4-四氢-5-甲氧基-N-丙基-2-萘胺
  参考文献：
  名称：

  Structure-activity relationships of dopaminergic 5-hydroxy-2-aminotetralin derivatives with functionalized N-alkyl substituents

  摘要：

  5-Hydroxy-2-aminotetralin derivatives in which one N-alkyl substituent carries a functional group have been prepared and their dopaminergic activities compared with those of 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) and known ergolines. Several members of the series demonstrated high affinities in dopamine (DA) receptor binding and DA agonist properties in the rotational behavior model in the range of known potent ergolines. The results suggest that the accessory binding site for the larger N-alkyl substituent of the 5-hydroxy-2-aminotetralins can accommodate various neutral and bulky functionalities and is probably identical with the site(s) to which the 8-substituents of the ergolines bind.

  DOI：

  10.1021/jm00156a007
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 platinum(IV) oxide 氢气 、 对甲苯磺酸 作用下， 反应 3.0h， 生成 (R)-(+)-2-(N-benzylamino)-5-methoxytetralin
  参考文献：
  名称：

  Fluorescent probes for dopamine receptors: synthesis and characterization of fluorescein and 7-nitrobenz-2-oxa-1,3-diazol-4-yl conjugates of D-1 and D-2 receptor ligands

  摘要：

  Fluorescent probes have been designed and developed for dopamine D-1 and D-2 receptors. Fluorescein and/or NBD (7-nitrobenz-2-oxa-1,3-diazol-4-yl) derivatives of PPHT (D-2 agonist), spiperone (D-2 antagonist), SKF 38393 (D-1 agonist), and SKF 83566 (D-1 antagonist) were synthesized via their amino-functionalized analogues and all ligands were pharmacologically evaluated by measuring their ability to displace [H-3]SCH 23390 and [H-3]spiperone from D-1 and D-2 receptor sites in caudate putamen of monkeys (Macaca fascicularis). The fluorescein derivatives of PPHT and SKF 83566 and the NBD derivatives of spiperone and SKF 83566 retained the high affinity and selectivity of the parent ligands. The NBD derivatives of PPHT showed higher D-2 receptor affinity and selectivity than their parent ligands. The enantiomers of the fluorescent derivatives of PPHT were also synthesized and were found to exhibit stereoselectivity in binding to the D-2 receptor, with the S enantiomers having a considerably higher affinity than their R analogues. In contrast to these results, the fluorescein derivative of SKF 38393 showed only a low affinity for the D-1 receptor. These fluorescein- and NBD-coupled D-1 and D-2 receptor ligands have considerable significance as potential probes in the study of distribution of the receptors at the cellular/subcellular level and of their mobility in membranes in normal/diseased states by use of fluorescence microscopic and fluorescence photobleaching recovery techniques, respectively. The development of these novel fluorescent probes should also provide new leads for the design and synthesis of additional fluorescent ligands with better fluorescent properties and/or higher affinity/selectivity for the DA receptors.

  DOI：

  10.1021/jm00115a012

文献信息

• Heterocyclyl-substituted- tetrahydro-napthalen-amine derivatives, their preparation and use as medicaments
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1975161A1

  公开（公告）日：2008-10-01

  The present invention relates to heterocyclyl-substituted-tetrahydro-naphtalen-amine compounds of general formula (I) methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans or animals, mediated by the 5-HT7 receptor affinity.

  本发明涉及一般式（I）的杂环基取代的四氢萘胺化合物，以及它们的制备方法，包含这些化合物的药物以及它们在制备用于治疗人类或动物的药物中的应用，通过5-HT7受体亲和力介导。
• Combination of a 5-HT7 receptor ligand and an opioid receptor ligand
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP1997493A1

  公开（公告）日：2008-12-03

  The present invention refers to a combination of a 5HT7 receptor ligand and an opioid recptor ligand, especially of a 5HT7 receptor agonist and an opioid recptor agonist, a medicament comprising this combination, or the use of this combination for the treatment of the symptoms of pain, the prevention or the prophylaxis of the symptoms of pain.

  本发明涉及一种5HT7受体配体和阿片受体配体的组合，特别是一种5HT7受体激动剂和阿片受体激动剂，包含该组合的药物，或者利用该组合治疗疼痛症状，预防或预防疼痛症状的用途。
• HETEROCYCLYL-SUBSTITUTED-TETRAHYDRO-NAPHTHALEN-AMINE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICAMENTS
  申请人：Garcia-Lopez Monica

  公开号：US20100105684A1

  公开（公告）日：2010-04-29

  The present invention relates to heterocyclyl-substituted-tetrahydro-naphthalen-amine compounds of general formula (I) and compositions thereof, methods for their preparation, and the use of said compounds for the treatment or prophylaxis of various disorders of humans or animals.

  本发明涉及一般式(I)的杂环取代四氢萘胺化合物及其组合物，其制备方法以及利用该化合物治疗或预防人或动物的各种疾病。
• COMBINATION OF A 5HT7 RECEPTOR LIGAND AND AN OPIOID RECEPTOR LIGAND
  申请人：Romero-Alonso Luz

  公开号：US20100197717A1

  公开（公告）日：2010-08-05

  The present invention refers to a combination of a 5HT7 receptor ligand and an opioid receptor ligand, especially of a 5HT7 receptor agonist and an opioid receptor agonist, a medicament comprising this combination, or the use of this combination for the treatment of the symptoms of pain, the prevention or the prophylaxis of the symptoms of pain.

  本发明涉及一种5HT7受体配体和阿片受体配体的组合，特别是5HT7受体激动剂和阿片受体激动剂的组合，包括此组合的药物，或者使用此组合治疗疼痛症状、预防或预防疼痛症状。
• Asymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir(III) Complexes Bearing a Chiral <i>N</i>-(2-Picolyl)sulfonamidato Ligand
  作者：Takuma Kawada、Kenya Yabushita、Toshihisa Yasuda、Takeshi Ohta、Takaaki Yajima、Kouichi Tanaka、Noriyuki Utsumi、Masahito Watanabe、Kunihiko Murata、Yoshihito Kayaki、Shigeki Kuwata、Takeaki Katayama

  DOI：10.1021/acs.joc.2c00580

  日期：2022.7.1

  A convenient asymmetric reductive amination of benzylic ketones (α-arylated ketones) catalyzed by newly designed Cp*Ir complexes bearing a chiral N-(2-picolyl)sulfonamidato ligand was developed. Using readily available β-amino alcohols as chiral aminating agents, a range of benzo-fused and acyclic ketones were successfully reduced with formic acid in methanol at 40 °C to afford amines with favorable

  开发了一种由新设计的带有手性N- (2-吡啶甲基) 磺胺基配体的 Cp*Ir 配合物催化的方便的苯甲基酮（α-芳基化酮）的不对称还原胺化。使用容易获得的 β-氨基醇作为手性胺化剂，一系列苯并稠合和无环酮在 40°C 的甲醇溶液中成功地用甲酸还原，得到具有良好化学和非对映选择性的胺。氨基醇衍生的手性助剂很容易被温和的周期性氧化剂去除，从而产生具有光学活性的伯 β-芳胺，而不会影响光学纯度（高达 97% ee）。即使将催化剂的用量与底物/催化剂 (S/C) 的比值降低 20,000，仍能保持优异的催化性能，并且可以在超过 100 g 的大规模上进行胺化。对可分离的氢化铱配合物和模型中间体（如N、O-缩醛、烯胺和亚胺化合物）的化学计量反应的机理研究表明，从酮底物和手性胺对应物产生的精确氢化物转移到亚胺物种。