3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate | 924637-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate
• 英文别名: methyl 4-oxo-7-(trifluoromethylsulfonyloxy)-2,3-dihydro-1H-naphthalene-2-carboxylate
• CAS: 924637-37-6
• 化学式: C₁₃H₁₁F₃O₆S
• 分子量: 352.288
• InChiKey: LGYLILANVUUEMD-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C(Solv: hexane (110-54-3))
• 沸点：
  434.1±45.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate 在 吡啶 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 96.0h， 生成 3-[(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)methyl]-3,4-dihydro-6-phenylnaphthalen-1(2H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotonin ligands

  摘要：

  A series of novel alpha-tetralone and a-tetralol derivatives was synthesized, and their binding affinities for 5-HT2A and D-2 receptors, the most important targets implicated in the anti-schizophrenia drug action, were evaluated to elucidate how substitutions in the aromatic ring of the pharmacophore affect to the affinity or selectivity for these receptors. The replacement of the H-7 in the tetrahydronaphthalene system by an amino group resulted in privileged 5-HT2A affinity of the 6-fluorobenzo[d]isoxazol derivative 36 and the alcohol 25 both showing a pK(i) value for 5-HT2A higher than 8.3 and good binding affinities for D-2 receptor leading to a Meltzer's ratio characteristic of an atypical antipsychotic profile. Additionally, a small collection of 3-aminomethyltetralone derivatives was prepared and examined here for their affinities and selectivities as 5-HT2A/D-2 dual ligands. Compound 11 shows the best profile with good pK(i) values for 5-HT2A and D-2 receptors leading to a Meltzer's ratio characteristic of a typical antipsychotic behaviour. These three compounds behaved as competitive antagonists of both 5-HT2A and D-2 receptors, and might be promising pharmacological tools for the investigation of the dual function of the 5HT(2A)-D-2 ligands. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.066
• 作为产物：
  描述：

  methyl 7-methoxy-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 吡啶 、 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 生成 3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate
  参考文献：
  名称：

  通过钯催化的交叉偶联反应合成取代的四氢萘酮作为CNS试剂的中间体

  摘要：

  通过Pd催化的3-（甲氧基羰基）-1,2,3,4-四氢-1-氧萘基-6-基三氟甲磺酸盐（5）的偶联反应合成了一系列取代的四氢萘酮作为CNS试剂的中间体有机金属试剂。

  DOI：

  10.1016/j.tetlet.2006.10.154

文献信息

• Synthesis of substituted tetralones as intermediates of CNS agents via palladium-catalyzed cross-coupling reactions
  作者：María Torrado、Christian F. Masaguer、Enrique Raviña

  DOI：10.1016/j.tetlet.2006.10.154

  日期：2007.1

  A series of substituted tetralones as intermediates of CNS agents has been synthesized via Pd-catalyzed coupling reactions of 3-(methoxycarbonyl)-1,2,3,4-tetrahydro-1-oxonaphthalen-6-yl trifluoromethanesulfonate (5) with a variety of organometallic reagents.

  通过Pd催化的3-（甲氧基羰基）-1,2,3,4-四氢-1-氧萘基-6-基三氟甲磺酸盐（5）的偶联反应合成了一系列取代的四氢萘酮作为CNS试剂的中间体有机金属试剂。
• Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotonin ligands
  作者：Laura Carro、María Torrado、Enrique Raviña、Christian F. Masaguer、Sonia Lage、José Brea、María I. Loza

  DOI：10.1016/j.ejmech.2013.10.066

  日期：2014.1

  A series of novel alpha-tetralone and a-tetralol derivatives was synthesized, and their binding affinities for 5-HT2A and D-2 receptors, the most important targets implicated in the anti-schizophrenia drug action, were evaluated to elucidate how substitutions in the aromatic ring of the pharmacophore affect to the affinity or selectivity for these receptors. The replacement of the H-7 in the tetrahydronaphthalene system by an amino group resulted in privileged 5-HT2A affinity of the 6-fluorobenzo[d]isoxazol derivative 36 and the alcohol 25 both showing a pK(i) value for 5-HT2A higher than 8.3 and good binding affinities for D-2 receptor leading to a Meltzer's ratio characteristic of an atypical antipsychotic profile. Additionally, a small collection of 3-aminomethyltetralone derivatives was prepared and examined here for their affinities and selectivities as 5-HT2A/D-2 dual ligands. Compound 11 shows the best profile with good pK(i) values for 5-HT2A and D-2 receptors leading to a Meltzer's ratio characteristic of a typical antipsychotic behaviour. These three compounds behaved as competitive antagonists of both 5-HT2A and D-2 receptors, and might be promising pharmacological tools for the investigation of the dual function of the 5HT(2A)-D-2 ligands. (C) 2013 Elsevier Masson SAS. All rights reserved.