methyl-3,4-dihydro-2-hydroxy-3-allyl-2-naphthalenecarboxylate | 171191-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl-3,4-dihydro-2-hydroxy-3-allyl-2-naphthalenecarboxylate
• 英文别名: methyl 2-oxo-3-prop-2-enyl-3,4-dihydro-1H-naphthalene-1-carboxylate
• CAS: 171191-84-7
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: DWCSPZMUIBIXAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl-3,4-dihydro-2-hydroxy-3-allyl-2-naphthalenecarboxylate 在 chromium(VI) oxide 、 硫酸 、 水 、 二(3-甲基丁烷-2-基)硼烷 、 对甲苯磺酸 、 二甲基亚砜 、 lithium chloride 作用下， 生成 3-(2'-(methoxycarbonyl)ethyl)-2-tetralone
  参考文献：
  名称：

  cis- and trans-N-Benzyl-octahydrobenzo[g]quinolines. Adrenergic and Dopaminergic Activity Studies

  摘要：

  In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and ct adrenoceptors. The trans N-benzyl analogues exhibited affinity at the alpha (2) as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the alpha (2) adrenoceptor. Enhanced activity for the alpha (2) receptors was also exhibited by the cia N-benzylated isomers. These observations are interpreted by theoretical calculations. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00076-2
• 作为产物：
  描述：

  β-四氢萘酮 在 sodium methylate 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 3.75h， 生成 methyl-3,4-dihydro-2-hydroxy-3-allyl-2-naphthalenecarboxylate
  参考文献：
  名称：

  A Diastereoselective Synthesis oftrans/cisOctahydronaphthoquinolizine

  摘要：

  The tetracyclic system of 2,3,6,7,7a,8,12b,12c-octahydro-1H,5H-naphtho[1,2,3,ij]quinolizine with trans/cis fusions of the B/D and B/C rings has been diastereospecifically synthesized in nine steps and in 23% total yield.

  DOI：

  10.1080/00397919508011436

文献信息

• A Diastereoselective Synthesis of<i>trans/cis</i>Octahydronaphthoquinolizine
  作者：Antonios Kouvarakis、Haralambos E. Katerinopoulos

  DOI：10.1080/00397919508011436

  日期：1995.10

  The tetracyclic system of 2,3,6,7,7a,8,12b,12c-octahydro-1H,5H-naphtho[1,2,3,ij]quinolizine with trans/cis fusions of the B/D and B/C rings has been diastereospecifically synthesized in nine steps and in 23% total yield.
• O-Arylation versus C-Arylation:  Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls
  作者：Yewen Fang、Chaozhong Li

  DOI：10.1021/jo060747t

  日期：2006.8.1

  The copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls via a six-membered ring closure was examined. With CuI (10 mol %) as the catalyst, N,N'-dimethylethylenediamine as the ligand, and Cs2CO3 as the base, the reactions of alpha-(2-bromobenzyl)-beta-keto esters in THF at refluxing temperature afforded the corresponding substituted 4H-1-benzopyrans in high yields via O-arylation. On the other hand, the reactions of delta-(2-bromophenyl)-beta-keto esters in refluxing dioxane led to the formation of 3,4-dihydronaphthalen-2(1H)-one derivatives via C-arylation.
• cis- and trans-N-Benzyl-octahydrobenzo[g]quinolines. Adrenergic and Dopaminergic Activity Studies
  作者：Kyriaki Thermos、George E Froudakis、Nikos Tagmatarchis、Haralambos E Katerinopoulos

  DOI：10.1016/s0960-894x(01)00076-2

  日期：2001.4

  In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and ct adrenoceptors. The trans N-benzyl analogues exhibited affinity at the alpha (2) as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the alpha (2) adrenoceptor. Enhanced activity for the alpha (2) receptors was also exhibited by the cia N-benzylated isomers. These observations are interpreted by theoretical calculations. (C) 2001 Published by Elsevier Science Ltd.