5,6-dimethoxy-2-phenyl-1-tetralone | 65144-89-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5,6-dimethoxy-2-phenyl-1-tetralone
• 英文别名: 5,6-Dimethoxy-2-phenyl-1-tetralon；5,6-dimethoxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 65144-89-0
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: IJAHNTKBUWAKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2-phenyl-1-tetralone 在 盐酸 、 sodium tetrahydroborate 、 三氯化铝 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 、 苯 为溶剂， 反应 3.58h， 生成 2-[(1R,2S)-5,6-dimethoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities

  摘要：

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

  DOI：

  10.1021/jm00158a016
• 作为产物：
  描述：

  α-Ethoxycarbonyl-benzyliden-triphenyl-phosphoran 在 palladium on activated charcoal 氢氧化钾 、 PPA 、 氢气 作用下， 以 乙醇 、 水 、 苯 为溶剂， 90.0 ℃ 、344.73 kPa 条件下， 反应 2.83h， 生成 5,6-dimethoxy-2-phenyl-1-tetralone
  参考文献：
  名称：

  Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of .alpha.1 and .alpha.2 adrenergic activities

  摘要：

  A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

  DOI：

  10.1021/jm00158a016

文献信息

• Studies on the structure-activity relationship of adrenergic .BETA.-mimetic benzylamine derivatives. IV. Aryl-substituted 1-aminotetralins and 1-aminoindans.
  作者：SHIRO YAMAMURA、KUNIYUKI ODA、TOMISHIGE MIZOGUCHI、SEIICHI SAITO、YOSHIO IWASAWA、MOTOAKI OHASHI、AKIO KIYOMOTO

  DOI：10.1248/cpb.26.3613

  日期：——

  The synthesis and adrenergic activity of the stereoisomeric aryl-substituted 1-aminotetralins (3, 4, and 7) and 1-aminoindans (5 and 6), rigid structures related to the benzylamine derivatives (2), are presented. Among this series of compounds tested, trans-5, 6-dihydroxy-1-methylamino-2-(3, 4, 5-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthalene (3b) was the most active tracheal relaxing compound, which was approximately ten times as active as the corresponding cis isomer (4b) and about two times as active as 2b. The structure-activity relationship in this series is discussed.

  本文介绍了立体异构芳基取代的 1-氨基四氢萘 (3、4 和 7) 和 1-氨基茚满 (5 和 6)的合成和肾上腺素活性，它们的刚性结构与苄胺衍生物 (2) 有关。在测试的这一系列化合物中，反式-5，6-二羟基-1-甲基氨基-2-（3，4，5-三甲氧基苯基）-1，2，3，4-四氢萘（3b）是最具活性的气管松弛化合物，其活性约为相应顺式异构体（4b）的 10 倍，约为 2b 的 2 倍。本文讨论了该系列化合物的结构-活性关系。
• DEBERNARDIS J. F.; WINN M.; ARENDSEN D. L.; KERKMAN D. J.; KYNCL J. J., J. MED. CHEM., 29,(1986) N 8, 1413-1417
  作者：DEBERNARDIS J. F.、 WINN M.、 ARENDSEN D. L.、 KERKMAN D. J.、 KYNCL J. J.

  DOI：——

  日期：——
• YAMAMURA S.; ODA K.; MIZOGUCHI T.; SAITO S.; IWASAWA Y.; OHASHI M.; KIYOM+, CHEM. AND PHARM. BULL., 1978, 26, NO 12, 3613-3623
  作者：YAMAMURA S.、 ODA K.、 MIZOGUCHI T.、 SAITO S.、 IWASAWA Y.、 OHASHI M.、 KIYOM+

  DOI：——

  日期：——