3,4-dihydro-4-phenylisoquinoline | 6187-58-2

• 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: 3,4-dihydro-4-phenylisoquinoline
• 英文别名: 4-phenyl-3,4-dihydroisoquinoline；3,4-dihydro-4-phenyl-isoquinoline；4-Phenyl-3,4-dihydro-isochinolin
• CAS: 6187-58-2
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: PQKKAOHDVLDMOM-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  133-134 °C(Press: 0.3 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 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：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-4-phenylisoquinoline 在 lithium aluminium tetrahydride 、 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 4.08h， 生成 2-ethyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Nortey, Samuel O.; McComsey, David F.; Maryanoff, Bruce E., Heterocycles, 1993, vol. 35, # 2, p. 1075 - 1088

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二苯基乙胺 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 9.0h， 生成 3,4-dihydro-4-phenylisoquinoline
  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

文献信息

• [EN] PROCESS FOR PRODUCING DIHYDROISOQUINOLINE ZWITTERIONS<br/>[FR] PROCEDE DE PRODUCTION DE ZWITTERIONS DE DIHYDROISOQUINOLINE
  申请人：PROCTER & GAMBLE

  公开号：WO2005047264A1

  公开（公告）日：2005-05-26

  This invention relates to a preparation of zwitterionic sulfates of substituted or unsubstituted 3, 4-dihydroisoquinoline.

  这项发明涉及制备取代或未取代3,4-二氢异喹啉的带电离子硫酸盐。
• Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships
  作者：Bruce E. Maryanoff、David F. McComsey、Joseph F. Gardocki、Richard P. Shank、Michael J. Costanzo、Samuel O. Nortey、Craig R. Schneider、Paulette E. Setler

  DOI：10.1021/jm00391a028

  日期：1987.8

  verified by enantiospecific synthesis starting with (+)-(R)-2-phenylpyrrolidine. Regarding the pendant phenyl ring, diverse substitution patterns were investigated. Those substitutions that were particularly unfavorable were 3',4',5'-trimethoxy (20b), 2',3',4',5',6'-pentafluoro (34b), 2'-trifluoromethyl (38b), 3',5'-bis(trifluoromethyl) (42b), 4'-n-butyl (44b), 2'-cyano (47b), 4'-methylsulfonyl (50b), and

  一系列吡咯并[2,1-a]异喹啉和相关化合物由于对丁苯那嗪诱导的上睑下垂和镇静作用以及对生物胺吸收的抑制作用而被检测为抗抑郁样活性。因此，我们已经鉴定出有史以来报道的一些最有效的TBZ诱导上睑下垂拮抗剂和一些最有效的多巴胺，去甲肾上腺素和血清素摄取抑制剂（在大鼠脑突触体中）。在这方面，特别值得注意的化合物分别是52b，29b，22b和48b。生物活性主要由反式异构体表现出来。而且，通过拆分四种化合物7b，24b，37b和48b，发现生物活性与（+）对映异构体亚组（在589 nm在MeOH中测得的盐）相关，对应于6S，10bR的绝对构型7b，37b，和48b，以及24b的6R，10bR配置。在（+）-24b X HBr上进行X射线测定，确定了其绝对构型；通过（+）-（R）-2-苯基吡咯烷开始的对映体特异性合成，验证了其他化合物的构型。关于侧苯环，研究了多种取代方式。那些特别不利的取代基是3'
• Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles
  作者：Pavol Jakubec、Dane M Cockfield、Madeleine Helliwell、James Raftery、Darren J Dixon

  DOI：10.3762/bjoc.8.64

  日期：——

  stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation

  已经开发了一种多功能硝基-曼尼希/内酰胺化级联，用于直接立体选择性合成重装饰的 5-硝基哌啶-2-ones 和相关杂环。在四组分一锅反应中合成了高度对映体富集的取代 5-硝基哌啶-2-one，结合对映选择性有机催化迈克尔加成与非对映选择性硝基-曼尼希/内酰胺化级联反应。杂环的原脱硝和化学选择性还原操作用于在取代哌啶的合成中安装连续和完全取代的立体中心。
• 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。
• Tetrahydroazeto [2,1-a]isoquinolines and methods for treating depression
  申请人：McNeilab, Inc.

  公开号：US04713386A1

  公开（公告）日：1987-12-15

  Tetrahydroazeto[2,1-a]isoquinoline of the formula (I): ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 are substituents and x and y are 0-2. Also pharmaceutical compositions for relieving depression in mammals, e.g. in humans, and methods for synthesis and use of formula (I) compounds as well as novel intermediates in the synthesis.

  公式（I）的四氢氮杂[2,1-a]异喹啉：其中R、R.sup.1、R.sup.2和R.sup.3是取代基，x和y为0-2。此外，还有用于缓解哺乳动物，例如人类，的抑郁症的药物组合物，以及公式（I）化合物的合成和使用方法，以及合成中的新型中间体。