(+/-)-3-butyl-3,4-dihydroisoquinolin-1-(2H)-one | 146470-69-1

• 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: (+/-)-3-butyl-3,4-dihydroisoquinolin-1-(2H)-one
• 英文别名: 3-butyl-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 146470-69-1
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: QRSASMUHGYHRBX-UHFFFAOYSA-N

物化性质

• 熔点：
  98-99.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  400.9±25.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-3-butyl-3,4-dihydroisoquinolin-1-(2H)-one 在 硫酸 、 potassium nitrate 作用下， 以67%的产率得到(+/-)-3-butyl-7-nitro-3,4-dihydroisoquinolin-1-(2H)-one
  参考文献：
  名称：

  Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors

  摘要：

  A series of 3 -alkyl-7 -substituted-1,2,3,4-tetrahydroisoquinolines was synthesized and these compounds were evaluated for their PNMT inhibitory potency and affinity for the (alpha(2)-adrenoceptor. 7-Nitro-, 7-bromo-, 7-aminosulfonyl-, or 7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs that possess a 3-alkyl substituent that is longer than a methyl group showed decreased PNMT inhibitory potency, except for 3-propyl-7-aminosulfonyl-THIQ, which displayed excellent PNMT inhibitory potency. The rank order for selectivity (PNMT vs the alpha(2)-adrenoceptor) is 3 -alkyl -7 -aminosulfonyl-THIQs congruent to 3-alkyl-7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs > 3-alkyl-7-nitro-THlQs > 3-alkyl-7-bromo-THIQs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.015
• 作为产物：
  描述：

  (+/-)-N-(methoxycarbonyl)-1-phenyl-2-aminohexane 在 PPA 作用下， 反应 0.25h， 以61%的产率得到(+/-)-3-butyl-3,4-dihydroisoquinolin-1-(2H)-one
  参考文献：
  名称：

  Exploring the active site of phenylethanolamine N-methyltransferase: 3-alkyl-7-substituted-1,2,3,4-tetrahydroisoquinoline inhibitors

  摘要：

  A series of 3 -alkyl-7 -substituted-1,2,3,4-tetrahydroisoquinolines was synthesized and these compounds were evaluated for their PNMT inhibitory potency and affinity for the (alpha(2)-adrenoceptor. 7-Nitro-, 7-bromo-, 7-aminosulfonyl-, or 7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs that possess a 3-alkyl substituent that is longer than a methyl group showed decreased PNMT inhibitory potency, except for 3-propyl-7-aminosulfonyl-THIQ, which displayed excellent PNMT inhibitory potency. The rank order for selectivity (PNMT vs the alpha(2)-adrenoceptor) is 3 -alkyl -7 -aminosulfonyl-THIQs congruent to 3-alkyl-7-N-2,2,2-trifluoroethylaminosulfonyl-THIQs > 3-alkyl-7-nitro-THlQs > 3-alkyl-7-bromo-THIQs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.015

文献信息

• Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of <i>N</i>-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature
  作者：Balu Ramesh、Masilamani Jeganmohan

  DOI：10.1021/acs.joc.2c00072

  日期：2022.5.6

  Co(III)-catalyzed regio- and chemoselective redox-neutral C–H annulation of arylamides/acrylamides with 1,3-dienes is described. The present annulation reaction was well suited with a less-reactive 1,3-butadiene. By employing this protocol, pharmaceutically important 3,4-dihydroisoquinolinones were synthesized in good yields. Furthermore, the prepared 3,4-dihydroisoquinolinones were converted into

  描述了 Co(III) 催化的区域选择性和化学选择性氧化还原中性 C-H 环化芳基酰胺/丙烯酰胺与 1,3-二烯。本发明的环化反应非常适合反应性较低的 1,3-丁二烯。通过采用该协议，药学上重要的 3，4-二氢异喹啉酮以良好的收率合成。此外，制备的 3,4-二氢异喹啉酮以良好的收率转化为非常重要的环氧乙烷衍生物。竞争实验和动力学同位素效应 (KIE) 研究提出并支持了一个合理的机械循环。
• DE1012605
  申请人：——

  公开号：——

  公开（公告）日：——
• Method for the preparation of tetrahydroisoquinolone derivatives
  申请人：SMITH KLINE FRENCH LAB

  公开号：US02647902A1

  公开（公告）日：1953-08-04
• SUBSTITUTED 2-ALKYL QUINAZOLINONE DERIVATIVES AS PARP INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP1763518B1

  公开（公告）日：2012-01-11