2,3,4,6,7,8-hexahydro-5(1H)-quinolinone | 1006-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6,7,8-hexahydro-5(1H)-quinolinone
• 英文别名: 1,2,3,4,7,8-Hexahydroquinolin-5(6H)-one；2,3,4,6,7,8-hexahydro-1H-quinolin-5-one
• CAS: 1006-51-5
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: FZUXNHFRXMLNHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,6,7,8-hexahydro-5(1H)-quinolinone 在 palladium on activated charcoal 、 Rh/Al₂O₃ sodium hydroxide 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 20.0~100.0 ℃ 、7.58 MPa 条件下， 反应 52.0h， 生成 1-methyl-cis-decahydro-quinolin-5-ol
  参考文献：
  名称：

  Theoretical and Experimental Studies of Asymmetric Organozinc Additions to Benzaldehyde Catalyzed by Flexible and Constrained γ-Amino Alcohols

  摘要：

  The cis-decalin based gamma-amino alcohols, 1-5, were synthesized, resolved, and employed as catalysts in the addition of organozincs to benzaldehyde. Despite large facial differentiation in the RZn adducts of the ligands, the enantioselectivities were found to be moderate. Transition structure calculations were done using several quantum chemical methods to examine the underlying causes of the selectivity for three gamma-amino alcohols, 1, 2, and 3. The tricyclic mu-oxo (6/4/4), rather than the bicyclic six-membered (6/6), transition structures were found to explain the observed enantioselectivity for 2 and 3. MP2 calculations gave the best correlation to the experimental results compared to B3LYP and HIP calculations. The conformational flexibility of the chiral ligands was found to be an important factor in the selectivity.

  DOI：

  10.1021/jo0262210
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉-5-酮 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 以65%的产率得到2,3,4,6,7,8-hexahydro-5(1H)-quinolinone
  参考文献：
  名称：

  Nitrones by heterolytic fragmentation of .gamma.-N-hydroxyamino sulfonates. Conversion of a decahydroquinoline to a perhydroazaazulene

  摘要：

  DOI：

  10.1021/jo00220a057

文献信息

• Hetero [f] fused carbocyclic pyridines as dopaminergic agents
  申请人：Warner-Lambert Company

  公开号：US04762843A1

  公开（公告）日：1988-08-09

  Hetero [f] fused carbocyclic pyridines are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as dopamine agonists with selectivity for the presynaptic dopamine receptor and are useful as dopaminergic, antipsychotic and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.

  描述了异构[f]融合的碳环吡啶，以及制备和制备相同的药物组合物的方法，这些药物组合物可作为选择性作用于突触前多巴胺受体的多巴胺激动剂，并可用作多巴胺能、抗精神病和降压剂，以及用于治疗与高催乳素血症相关的疾病和中枢神经系统疾病。
• Efficient synthesis of β-amino-α,β-unsaturated carbonyl compounds
  作者：Yuanhong Zhao、Jingfeng Zhao、Yongyun Zhou、Ze Lei、Liang Li、Hongbin Zhang

  DOI：10.1039/b419254k

  日期：——

  β-enaminones is presented: in the presence of tetraethyl orthosilicate, a number of highly functional β-enamino esters were obtained; this method provided an alternative for the formation of β-amino-α,β-unsaturated carbonyl compounds with mild and functional group compatible reaction conditions.

  提出了一种用于合成β-烯胺酯和β-烯酮的通用且高产的方法：在原硅酸四乙酯存在下，获得了许多高官能度的β-烯胺酯。该方法为形成具有温和且与官能团相容的反应条件的β-氨基-α，β-不饱和羰基化合物提供了另一种方法。
• Rearrangements of Bicyclic Nitrones to Lactams:  Comparison of Photochemical and Modified Barton Conditions
  作者：Yibin Zeng、Brenton T. Smith、John Hershberger、Jeffrey Aubé

  DOI：10.1021/jo035004b

  日期：2003.10.1

  The rearrangement of nitrones to lactams can be carried out by photochemical activation or by treatment with Tf(2)O followed by KOH-promoted rearrangement (a modification of conditions originally introduced by Barton). Substrates in which the nitrone is part of a fused bicyclic ring system have traditionally proven problematic for this kind of reaction. In this study, a series of mono-, bi-, and tricyclic

  将硝酮重排成内酰胺可以通过光化学活化或通过用Tf（2）O处理，然后进行KOH促进的重排（对Barton最初引入的条件的修改）来进行。传统上证明，其中硝酮是稠合双环系统一部分的底物对于这种反应是有问题的。在这项研究中，准备了一系列单环，双环和三环稠合的硝酮，以研究产物对硝酮环大小和系链长度的依赖性。结果表明，苯中硝酮的光化学重排可提供相当不错的内酰胺收率（30-68％），而两步非光化学过程可提供相同目标的平均收率稍高（30-95％）。
• Intramolecular 1,3-dipolar cycloaddition of alkylazide-enones and rearrangements of the triazoline intermediates
  作者：Chin-Kang Sha、Sheng-Lian Ouyang、Der-Yung Hsieh、Tzong-Hsiung Hseu

  DOI：10.1039/c39840000492

  日期：——

  The intramolecular 1,3-dipolar cycloaddition of alkylazide-enones is followed by several novel rearrangements.

  烷基叠氮化物-烯酮的分子内1,3-偶极环加成反应之后是几种新颖的重排。
• Dopamine autoreceptor agonists as potential antipsychotics. 3. 6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine
  作者：Bradley W. Caprathe、Juan C. Jaen、Lawrence D. Wise、Thomas G. Heffner、Thomas A. Pugsley、Leonard T. Meltzer、Masood Parvez

  DOI：10.1021/jm00113a010

  日期：1991.9

  A series of rigid tricyclic analogues of the dopamine (DA) agonist PD 118440 [4-(1,2,5,6-tetrahydro-1-propyl-3-pyridinyl)-2-thiazolamine] was synthesized and evaluated for dopaminergic activity and DA autoreceptor selectivity. (R)-(+)-6-Propyl-4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine ((+)-6) was identified as the most selective DA autoreceptor agonist from this group of compounds. It inhibited spontaneous locomotor activity (LMA) in rodents, reversed the gamma-butyrolactone (GBL) induced accumulation of rat striatal DOPA and inhibited brain DA neuronal firing, all suggestive of direct DA autoreceptor agonist activity. However, (+)-6 is not completely free of postsynaptic DA activity, as evidenced by its stimulation of LMA in rats at high doses and its ability to produce stereotypy. On the other hand, (-)-6 appears to be a weak partial DA agonist with some effects on brain DA synthesis only at high doses. Like other DA autoreceptor agonists and DA antagonists, (+)-6 inhibited Sidman conditioned avoidance in squirrel monkeys, a test predictive of clinical antipsychotic activity. However, unlike classical antipsychotics, (+)-6 did not induce dystonias in haloperidol-sensitized squirrel monkeys, suggesting a minimal propensity toward extrapyramidal side effects (EPS).