methyl 8,9-dihydro-4-methoxy-7H-benzoquinoline-2-carboxylate | 94726-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 8,9-dihydro-4-methoxy-7H-benzoquinoline-2-carboxylate
• 英文别名: methyl 8,9-dihydro-4-methoxy-7H-benzo[de]quinoline-2-carboxylate；methyl 4-methoxy-8,9-dihydro-7H-benzo[de]quinoline-2-carboxylate
• CAS: 94726-27-9
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: HMNCNSROCUMWHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  457.9±45.0 °C(predicted)
• 密度：
  1.238±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 8,9-dihydro-4-methoxy-7H-benzoquinoline-2-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 以95%的产率得到8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinecarboxamide
  参考文献：
  名称：

  Design, synthesis and melatoninergic potency of new N-acyl 8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinalkanamines

  摘要：

  A series of new N-acyl 8,9-dihydro-4-metlioxy-7H-2-benzo[de]quinolinalkanamines have been prepared and tested for their ability to activate pigment granule aggregation in Xenopus laevis melanophores and bind to the recombinant human MT1 and MT2 melatonin receptor subtypes expressed in NIH 3T3 cells. Compounds with a single methylene spacer in the side chain (7) have no agonist activity, but are weak antagonists in the Xenopus melanophore assay, irrespectively of the size or shape of the R substituent (R = CH3 to c-C4H7). In contrast, compounds with two (8) or three (9) methylene spacers show partial agonist activity, though this does vary with the nature of the R substituent. Interestingly, the cyclopropane and cyclobutane R substituents, which are usually linked with antagonism, render the cyclopropanecarboxamido analog 9d and its cyclobutane-carboxamido congener 9e weak agonists. It seems, therefore, that in these compounds the R substituent constitutes a functional probe in the dynamic agonist-antagonist conformational equilibrium. One of the new molecules, antagonist 8c, exhibits a noteworthy MT2 subtype selectivity (13-fold), whereas the acetamido analog 9a (with a three methylene units spacer) also acts as an antagonist and is the only analog exhibiting MT1 selectivity (> 10-fold). In contrast to the analogous N1-C7 annulated indole derivatives, recently reported, the new C1-C8 condensed isoquinolines are not all pure antagonists. Despite their modest receptor affinity at the binding site these compounds demonstrate that the nature of the response (agonist or antagonist activity) is dependent, in this case, on both the side chain spacer's length and the size and shape of the R group. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2006.11.006
• 作为产物：
  描述：

  8-bromo-7-methoxy-3,4-dihydronaphthalen-1(2H)-one ethylene acetal 在 盐酸 、 正丁基锂 、 sodium methylate 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 39.25h， 生成 methyl 8,9-dihydro-4-methoxy-7H-benzoquinoline-2-carboxylate
  参考文献：
  名称：

  杂环合成中的乙烯基叠氮化物。第6部分。通过分子内的氮杂-维蒂希反应合成异喹啉

  摘要：

  含有邻-羰基取代基的叠氮肉桂酸酯是用于杂环合成的通用中间体。异喹啉（8）和（9）在中等中性条件下通过亚氨基三磷酸亚氨基的分子内aza-Wittig反应形成，亚氨基三氢呋喃分别易于从叠氮化物（1）和（2）衍生而来。氮杂荧蒽（10）也可以通过可分离的亚氨基正膦（11）和（12）由叠氮化物（3）制备。叠氮化物（1）在甲苯或二甲苯中的热解产生了4-取代的吲哚（13）的产量（表2）。类似地，吲哚（14）和（19）分别由叠氮化物（3）和（6a和b）形成。

  DOI：

  10.1039/p19870000921

文献信息

• Synthesis of isoquinolines by intramolecular aza-Wittig reaction
  作者：Deirdre M. B. Hickey、A. Roderick MacKenzie、Christopher J. Moody、Charles W. Ress

  DOI：10.1039/c39840000776

  日期：——

  Isoquinolines (3) and (5) are formed under miled neutral conditions by intramolecular aza-Wittig reactions of iminophospranes, readily derived from azides (1) and (4) with trithyl phosphite, the azafluranthene (7) can also be prepared from the isolable iminophosphoranes (8), (9), and (10).

  异喹啉（3）和（5）是在中性条件下通过亚磷酰胺的分子内氮杂-维蒂希反应形成的，亚氨基呋喃（7）可以容易地从叠氮化物（1）和（4）衍生而来，亚氨基正膦（8），（9）和（10）。
• HICKEY, D. M. B.;MACKENZIE, A. R.;MOODY, CH. J.;REES, CH. W., J. CHEM. SOC. CHEM. COMMUN., 1984, N 12, 776-777
  作者：HICKEY, D. M. B.、MACKENZIE, A. R.、MOODY, CH. J.、REES, CH. W.

  DOI：——

  日期：——
• HICKEY D. M. B.; MACKENZIE A. R.; MOODY CH. J.; REES CH. W., J. CHEM. SOC. PERKIN TRANS.,(1987) N 4, 921-926
  作者：HICKEY D. M. B.、 MACKENZIE A. R.、 MOODY CH. J.、 REES CH. W.

  DOI：——

  日期：——