methyl 1-hydroxy-5,6,7,8-tetrahydro-2-naphthoate | 54815-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1-hydroxy-5,6,7,8-tetrahydro-2-naphthoate
• 英文别名: methyl 1-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate；1-hydroxy-5,6,7,8-tetrahydro-[2]naphthoic acid methyl ester；Tetralol-(5)-carbonsaeure-(6)-methylester；1-Hydroxy-5,6,7,8-tetrahydro-[2]naphthoesaeure-methylester
• CAS: 54815-88-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: AMBJIFDYCIFVBA-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±42.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-hydroxy-5,6,7,8-tetrahydro-2-naphthoate 在 乙醇 、 一水合肼 作用下， 生成 1-hydroxy-5,6,7,8-tetrahydro-[2]naphthoic acid isopropylidenehydrazide
  参考文献：
  名称：

  Schroeter, Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-(2-ethenylcyclohexyl)-3-oxopropanoate 在 copper diacetate 、 manganese triacetate 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以46%的产率得到methyl 1-hydroxy-5,6,7,8-tetrahydro-2-naphthoate
  参考文献：
  名称：

  Manganese(III)-based oxidative free-radical cyclizations. Oxidative cyclization and aromatization of 3-oxo-6-heptenoate esters

  摘要：

  DOI：

  10.1021/jo00262a016

文献信息

• Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core
  作者：Yuan He、Jinghua Tang、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.orglett.8b01273

  日期：2018.7.20

  A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane

  描述了一种区域选择性和化学选择性方法，用于通过还原萘酚催化合成生物学上令人感兴趣的5,6,7,8-四氢萘酚。使用甲醇中的氢硅烷可选择性地还原萘酚中的侧链芳香烃，从而使功能性酚骨架保持完整。它提供了一个罕见的示例，该示例使用低成本且空气稳定的氢化硅烷在温和条件下催化还原未活化的芳烃。该反应是可扩展的，并且以高选择性进行，而没有形成1,2,3,4-四氢萘酚副产物，其可耐受敏感的官能团，例如溴化物，氯化物，氟化物，酮，酯和酰胺。
• [EN] AMIDE DERIVATIVES AS SELECTIVE SEROTONIN RE-UPTAKE INHIBITORS<br/>[FR] DERIVES D'AMIDE EN TANT QU'INHIBITEURS SELECTIFS DU RECAPTAGE DE LA SEROTONINE
  申请人：PFIZER LTD

  公开号：WO2004111003A1

  公开（公告）日：2004-12-23

  The present invention relates to compounds of formula (I), wherein R1 is selected from: (a) (C1-C6)alkyl, optionally substituted by 1-3 substituents, each independently selected from: (i) CF3, OH, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy and halo; (ii) Phenyl, optionally fused with phenyl or cyclohexyl, said phenyl or fused phenyl optionally substituted with 1-3 groups selected from (C1-C6)alkyl, (C1-C6)alkyl ester, OH and halo; and (b) (C3-C6)cycloalkyl, optionally fused with (C5-C7)cycloalkyl, said cycloalkyl or fused cycloalkyl optionally substituted by OH, (C1-C6)alkyl, (C1-C6)alkoxy and halo. R2 is Phenyl, optionally fused to (C4-C6)cycloalkyl, phenyl or pyridyl, said phenyl or fused phenyl moiety optionally substituted with 1-3 groups each independently selected from (C1-C6)alkyl, (C1-C6)alkoxy, halo and OH. n is 1 to 2 and pharmaceutically acceptable salts, solvates or polymorphs thereof; With the proviso that when n is 2 and R1 is 2-(3,4-dimethoxylphenyl)-1-ethyl, 3,3­diphemyl-1-propyl or 2,4-difluorophenyl, then R2 cannot be 4-trifluoromethoxyphenyl, 2,4,6-trimethoxyphenyl, 4-acetoxyphenyl or 2,4-difluorophenyl; which are a class of selective serotonin re-uptake inhibitors (SSRIs).

  本发明涉及式(I)的化合物，其中R1从以下选项中选择：(a) (C1-C6)烷基，可选地被1-3个取代基取代，每个取代基独立地从以下选项中选择：(i) CF3，OH，(C1-C6)烷基，(C3-C6)环烷基，(C1-C6)烷氧基和卤素；(ii) 苯基，可选地与苯基或环己基融合，所述苯基或融合苯基可选地被1-3个取代基取代，所述取代基独立地从(C1-C6)烷基，(C1-C6)烷基酯，OH和卤素中选择；和(b) (C3-C6)环烷基，可选地与(C5-C7)环烷基融合，所述环烷基或融合环烷基可选地被OH，(C1-C6)烷基，(C1-C6)烷氧基和卤素取代。R2为苯基，可选地融合到(C4-C6)环烷基，苯基或吡啶基，所述苯基或融合苯基基团可选地被1-3个取代基取代，每个取代基独立地从(C1-C6)烷基，(C1-C6)烷氧基，卤素和OH中选择。n为1至2，以及其药学上可接受的盐、溶剂化合物或多形体；但是当n为2且R1为2-(3,4-二甲氧基苯基)-1-乙基，3,3-二苯基-1-丙基或2,4-二氟苯基时，R2不能为4-三氟甲氧基苯基，2,4,6-三甲氧基苯基，4-乙酰氧基苯基或2,4-二氟苯基；这些是一类选择性5-羟色胺再摄取抑制剂（SSRIs）。
• Selective Benzopyranone and Pyrimido[2,1-<i>a</i>]isoquinolin-4-one Inhibitors of DNA-Dependent Protein Kinase:  Synthesis, Structure−Activity Studies, and Radiosensitization of a Human Tumor Cell Line in Vitro
  作者：Roger J. Griffin、Gabriele Fontana、Bernard T. Golding、Sophie Guiard、Ian R. Hardcastle、Justin J. J. Leahy、Niall Martin、Caroline Richardson、Laurent Rigoreau、Martin Stockley、Graeme C. M. Smith

  DOI：10.1021/jm049526a

  日期：2005.1.1

  scaffolds were less potent. Crucially, these studies revealed a very constrained structure-activity relationship at the 2-position of the benzopyranone and pyrimido[2,1-a]isoquinolin-4-one pharmacophore, with only a 2-morpholino or 2-(2'-methylmorpholino) group being tolerated at this position. More detailed biological studies conducted with the most potent inhibitor NU7163 (48; IC(50) = 0.19 microM) demonstrated

  合成了各种各样的chromen-2-one，chromen-4-one和pyrimidoisoquinolin-4-one衍生物，并评估了其对DNA修复酶DNA依赖性蛋白激酶（DNA-PK）的抑制活性，目的是阐明效价和激酶选择性的构效关系。DNA-PK抑制活性在评估的一系列化合物（IC（50）值范围从0.19到> 10 microM）上有很大差异，其中7,8-苯并铬基-4-酮和嘧啶基[2,1]表现出优异的活性。 -a] isoquinolin-4-one模板。相比之下，基于苯并色素-2-酮（香豆素）或2-芳基-7,8-苯并色素-4-酮（黄酮）支架的抑制剂效力较低。至关重要的是，这些研究揭示了在苯并吡喃酮和嘧啶基2位上的结构活性关系非常受约束[2，1-a]异喹啉-4-酮药效基团，在此位置仅可耐受2-吗啉代或2-（2'-甲基吗啉代）基团。用最有效的抑制剂NU7163（48; IC（50）= 0
• Amide derivatives as selective serotonin re-uptake inhibitors
  申请人：Andrews David Mark

  公开号：US20050014789A1

  公开（公告）日：2005-01-20

  The present invention relates to compounds of formula (I), wherein R 1 is selected from: (a) (C 1 -C 6 )alkyl, optionally substituted by 1-3 substituents, each independently selected from: (i) CF 3 , OH, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkoxy and halo. (ii) Phenyl, optionally fused with phenyl or cyclohexyl, said phenyl or fused phenyl optionally substituted with 1-3 groups selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl ester, OH and halo; and (b) (C 3 -C 6 )cycloalkyl, optionally fused with (C 5 -C 7 )cycloalkyl, said cycloalkyl or fused cycloalkyl optionally substituted by OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and halo. R 2 is Phenyl, optionally fused to (C 4 -C 6 )cycloalkyl, phenyl or pyridyl, said phenyl or fused phenyl moiety optionally substituted with 1-3 groups each independently selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo and OH; n is 1 to 2; and pharmaceutically acceptable salts, solvates or polymorphs thereof; With the proviso that when n is 2 and R 1 is 2-(3,4-dimethoxylphenyl)-1-ethyl, 3,3-diphenyl-1-propyl or 2,4-difluorophenyl, then R 2 cannot be 4-trifluoromethoxyphenyl, 2,4,6-trimethoxyphenyl, 4-acetoxyphenyl or 2,4-difluorophenyl; which are a class of selective serotonin re-uptake inhibitors (SSRIs).

  本发明涉及式（I）的化合物，其中R1选自：（a）（C1-C6）烷基，可选地被1-3个取代基取代，每个取代基独立地选自：（i）CF3，OH，（C1-C6）烷基，（C3-C6）环烷基，（C1-C6）烷氧基和卤素；（ii）苯基，可选地与苯基或环己基融合，所述苯基或融合苯基可选地被1-3个选自（C1-C6）烷基，（C1-C6）烷酯，OH和卤素的基团取代；和（b）（C3-C6）环烷基，可选地与（C5-C7）环烷基融合，所述环烷基或融合环烷基可选地被OH，（C1-C6）烷基，（C1-C6）烷氧基和卤素取代。R2为苯基，可选地融合到（C4-C6）环烷基、苯基或吡啶基上，所述苯基或融合苯基基团可选地被1-3个独立选自（C1-C6）烷基，（C1-C6）烷氧基，卤素和OH的基团取代；n为1到2；以及其药学上可接受的盐、溶剂或多型性；但当n为2且R1为2-(3,4-二甲氧基苯基)-1-乙基、3,3-二苯基-1-丙基或2,4-二氟苯基时，则R2不能是4-三氟甲氧基苯基、2,4,6-三甲氧基苯基、4-乙酰氧基苯基或2,4-二氟苯基；这是一类选择性5-羟色胺再摄取抑制剂（SSRI）。
• Hueckel; Goth, Chemische Berichte, 1924, vol. 57, p. 1290
  作者：Hueckel、Goth

  DOI：——

  日期：——