3-(2-bromoethyl)-1,2-dihydro-6-methoxynaphthalene | 184347-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-bromoethyl)-1,2-dihydro-6-methoxynaphthalene
• 英文别名: 3-(2-Bromoethyl)-6-methoxy-1,2-dihydronaphthalene
• CAS: 184347-22-6
• 化学式: C₁₃H₁₅BrO
• 分子量: 267.166
• InChiKey: ZBNHKHXGIVUBJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethyl)-1,2-dihydro-6-methoxynaphthalene 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 4-[2-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)ethyl]-1-phenylpiperazine
  参考文献：
  名称：

  Structure−Activity Relationship Studies on the 5-HT_1A Receptor Affinity of 1-Phenyl-4-[ω-(α- or β-tetralinyl)alkyl]piperazines. 4

  摘要：

  The synthesis of 1-phenylpiperazines, linked in the alpha or beta position of the tetralin moiety on the terminal part of the N-4 alkyl chain, and their radioligand binding affinities for 5-HT1A, 5-HT2A, D-1, D-2, alpha(1), and alpha(2) receptors along with SAR studies on the 5-HT1A receptor are reported. Several changes have been carried out on previous structures of type 2, by inserting the alkyl chain with variable length in the alpha or beta position of the tetralin moiety and by changing the position of the methoxy group on the aromatic ring of the tetralin nucleus. The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT1A receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position.

  DOI：

  10.1021/jm9604538
• 作为产物：
  描述：

  7-methoxyspiro[3,4-dihydro-1H-naphthalene-2,1'-cyclopropane]-1-ol 在 氢溴酸 作用下， 反应 22.0h， 生成 3-(2-bromoethyl)-1,2-dihydro-6-methoxynaphthalene
  参考文献：
  名称：

  Structure−Activity Relationship Studies on the 5-HT_1A Receptor Affinity of 1-Phenyl-4-[ω-(α- or β-tetralinyl)alkyl]piperazines. 4

  摘要：

  The synthesis of 1-phenylpiperazines, linked in the alpha or beta position of the tetralin moiety on the terminal part of the N-4 alkyl chain, and their radioligand binding affinities for 5-HT1A, 5-HT2A, D-1, D-2, alpha(1), and alpha(2) receptors along with SAR studies on the 5-HT1A receptor are reported. Several changes have been carried out on previous structures of type 2, by inserting the alkyl chain with variable length in the alpha or beta position of the tetralin moiety and by changing the position of the methoxy group on the aromatic ring of the tetralin nucleus. The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT1A receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position.

  DOI：

  10.1021/jm9604538

文献信息

• Structure−Activity Relationship Studies on the 5-HT_1A Receptor Affinity of 1-Phenyl-4-[ω-(α- or β-tetralinyl)alkyl]piperazines. 4
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella、Maria Gioia Fornaretto、Carla Caccia、Robert A. McArthur

  DOI：10.1021/jm9604538

  日期：1996.1.1

  The synthesis of 1-phenylpiperazines, linked in the alpha or beta position of the tetralin moiety on the terminal part of the N-4 alkyl chain, and their radioligand binding affinities for 5-HT1A, 5-HT2A, D-1, D-2, alpha(1), and alpha(2) receptors along with SAR studies on the 5-HT1A receptor are reported. Several changes have been carried out on previous structures of type 2, by inserting the alkyl chain with variable length in the alpha or beta position of the tetralin moiety and by changing the position of the methoxy group on the aromatic ring of the tetralin nucleus. The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT1A receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position.