ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate | 57231-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate
• 英文别名: Ethyl-3,4-dihydro-6,7-dimethoxy-1-isochinolinpropionat；3-(6,7-dimethoxy-3,4-dihydro-isoquinolin-1-yl)-propionic acid ethyl ester；Ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propanoate
• CAS: 57231-75-1
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: WTYRRVAMZFKMBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate 在 盐酸 、 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 乙醇 、 二氯甲烷 、 丁酮 、 苯 为溶剂， 反应 12.0h， 生成 ethyl (9,10-dimethoxy-3β-hydroxy-1,2,4,6,7,11bα-hexahydro-3H-benzoquinolizin-4α-yl)carboxylate
  参考文献：
  名称：

  Blasko, Gabor; Kardos, Julianna; Baitz-Gacs, Eszter, Heterocycles, 1986, vol. 24, # 10, p. 2887 - 2900

  摘要：

  DOI：
• 作为产物：
  描述：

  丁二酸单乙酯酰氯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate
  参考文献：
  名称：

  Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones

  摘要：

  The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a]isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.033

文献信息

• Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones
  作者：Laura Moreno、Javier Párraga、Abraham Galán、Nuria Cabedo、Jaime Primo、Diego Cortes

  DOI：10.1016/j.bmc.2012.09.033

  日期：2012.11

  The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a]isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
• Blasko, Gabor; Kardos, Julianna; Baitz-Gacs, Eszter, Heterocycles, 1986, vol. 24, # 10, p. 2887 - 2900
  作者：Blasko, Gabor、Kardos, Julianna、Baitz-Gacs, Eszter、Simonyi, Miklos、Szantay, Csaba

  DOI：——

  日期：——