3,4-二氢-4-苯基异喹啉盐酸盐 | 10016-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 中文名称: 3,4-二氢-4-苯基异喹啉盐酸盐
• 英文名称: 3,4-dihydro-4-phenylisoquinoline hydrochloride
• 英文别名: 4-Phenyl-3,4-dihydroisoquinoline;hydrochloride
• CAS: 10016-59-8
• 化学式: C₁₅H₁₃N*ClH
• 分子量: 243.736
• InChiKey: XXFZLVUYQSMDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-二氢-4-苯基异喹啉盐酸盐 反应 1.5h， 生成
  参考文献：
  名称：

  Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s

  摘要：

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.

  DOI：

  10.1021/jm00364a013
• 作为产物：
  描述：

  3,4-dihydro-4-phenylisoquinoline 、 盐酸 以62%的产率得到
  参考文献：
  名称：

  MARYANOFF B. E.; MCCOMSEY D. F.; TAYLOR R. J.; GARDOCKI J. F., J. MED. CHEM., 1981, 24, NO 1, 79-88

  摘要：

  DOI：

文献信息

• Synthesis and stereochemistry of 7-phenyl-2-propionanilidobenzo[a]quinolizidine derivatives. Structural probes of fentanyl analgesics
  作者：Bruce E. Maryanoff、David F. McComsey、Russell J. Taylor、Joseph F. Gardocki

  DOI：10.1021/jm00133a017

  日期：1981.1

  of rat brain. Stereochemical assignments for 7c, 7d, 9c, and 9d were deduced from NMR spectral analyses. Conformational analysis revealed that the 2 alpha isomers (7d and 9d) exist in solution as mixtures of cis- and trans-fused conformers with ca. 90 and 45% cis form, respectively. Other compounds (12a, 12b, and 14) related to these propionanilides were also prepared, stereochemically characterized

  N-（1,3,4,6,7,11b-六氢-7-苯基-2H-苯并[a]喹啉嗪-2-基）-N-苯基丙酰胺的非对映异构体（7c，7d，9c和9d合成了芬太尼的构象受限的类似物），并分别测试了其对大鼠脑的阿片受体的镇痛活性和亲和力。从NMR光谱分析推导出7c，7d，9c和9d的立体化学分配。构象分析表明，溶液中存在2个α异构体（7d和9d），为顺式和反式构象异构体与ca的混合物。分别为90和45％的顺式形式。还制备了与这些丙酰苯胺有关的其他化合物（12a，12b和14），并进行了化学表征和测试。观察到7d的镇痛作用较弱，并且7d和9d均以约50的I50与阿片受体结合。分别为1100和1500 nM（约0。5％的芬太尼和2％的吗啡）。阿片拮抗剂纳洛酮取消了7d的镇痛作用。
• US4421917A
  申请人：——

  公开号：US4421917A

  公开（公告）日：1983-12-20
• Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s
  作者：Joan M. Caroon、Robin D. Clark、Arthur F. Kluge、Chi Ho Lee、Arthur M. Strosberg

  DOI：10.1021/jm00364a013

  日期：1983.10

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.
• MARYANOFF B. E.; MCCOMSEY D. F.; TAYLOR R. J.; GARDOCKI J. F., J. MED. CHEM., 1981, 24, NO 1, 79-88
  作者：MARYANOFF B. E.、 MCCOMSEY D. F.、 TAYLOR R. J.、 GARDOCKI J. F.

  DOI：——

  日期：——