1,2,3,4-四氢-6H-吡啶并[1,2-b]异喹啉-6-酮 | 76352-35-7

• 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
• 中文名称: 1,2,3,4-四氢-6H-吡啶并[1,2-b]异喹啉-6-酮
• 英文名称: 1,2,3,4-Tetrahydro-6H-benzoquinolizine-6-one
• 英文别名: 1,2,3,4-tetrahydro-6H-benzoquinolizin-6-one；1,2,3,4-tetrahydropyrido[1,2-b]isoquinolin-6-one；1,3,4,6-tetrahydro-2H-benzo[b]quinolizin-6-one；1,2,3,4-tetrahydrobenzo[b]quinolizin-6-one
• CAS: 76352-35-7
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: SXPPWRPADOMFPG-UHFFFAOYSA-N

物化性质

• 熔点：
  100-103 °C
• 沸点：
  385.0±35.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢-6H-吡啶并[1,2-b]异喹啉-6-酮 在 钯 盐酸 作用下， 以 乙醇 为溶剂， 以94%的产率得到benzo[b]quinolizidin-6-one
  参考文献：
  名称：

  Amidine and isothiourea derivatives, compositions containing them and

  摘要：

  提供了化合物的新颖化合物，其化学式为（I）##STR1## 其中X、R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5如规范中定义的那样，以及它们的光学异构体和拉克酸盐，以及其制备过程、含有它们的组合物以及它们在治疗中的应用。

  公开号：

  US05929085A1
• 作为产物：
  描述：

  N-甲氧基苯甲酰胺 在 titanium(III) chloride 、 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.83h， 生成 1,2,3,4-四氢-6H-吡啶并[1,2-b]异喹啉-6-酮
  参考文献：
  名称：

  O-Methylarenehydroxamates as ortho-lithiation directing groups. Titanium(III)-mediated conversion of O-methyl hydroxamates to primary amides

  摘要：

  Reaction of O-methyl benzohydroxamates 2a-c with sec-butyllithium in the presence of TMEDA at -40-degrees-C regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g. 3). These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, giving adducts which on reduction with TiCl3 are converted into ortho-substituted primary benzamides in excellent yields. Ortho lithiation of O-methyl benzohydroxamates is thus formally equivalent to ortho lithiation of primary benzamides themselves. The utility of these synthetic operations is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups. The conversion of 0-methyl hydroxamates to primary amides is shown to be general, as exemplified by transformation of 14a-f to 15a-f.O-Methyl 2-methylbenzohydroxamate (4a) undergoes regiospecific dilithiation on nitrogen and on the methyl group when treated with sec-butyllithium at -70-degrees-C. These dilithio species react with DMF or ''Weinreb-type'' amides to give condensation products which cyclize to N-methoxyisoquinolin-1(2H)-ones under mildly acidic conditions. Removal of the N-methoxy moiety under conditions analogous to those used for O-methyl benzohydroxamate provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency. This process is exemplified by the synthesis of isoquinolin-1(2H)-one 9a, its 3-n-butyl congener 9b, and the tricyclic isoquinolin-1 (2H)-ones 20a and 20b from O-methyl 2-methylbenzohydroxamate (4a).

  DOI：

  10.1021/jo00066a014

文献信息

• One-shot access to isoquinolone and (hetero)izidinone architectures using cyclic α-chloro eneformamides and cyclic anhydrides
  作者：Timothy K. Beng、Spencer Langevin、Abdikani Omar Farah、Joshua Goodsell、Katie Wyatt

  DOI：10.1039/c8nj06539j

  日期：——

  describe a direct and modular approach to [6,n] and [7,n]-1-azabicyclic unsaturated lactams, most of which bear at least one endocyclic heteroatom. A site-selective hexannulation reaction between cyclic α-chloro eneformamides and cyclic anhydrides is implicated. The scope of the anhydride component in a Castagnoli–Cushman reaction has been extended beyond 5-, 6-, and 7-membered rings.

  功能化的叠氮酮和异喹啉酮是生物活性分子中常见的基序。在这里，我们描述了[6，n ]和[7，n ] -1-氮杂双环不饱和内酰胺的直接和模块化方法，其中大多数带有至少一个内环杂原子。涉及环状α-氯代烯甲酰胺和环状酸酐之间的选择性位六价反应。Castagnoli-Cushman反应中酸酐组分的范围已扩展到5元，6元和7元环。
• Radical cyclizations to quinolone and isoquinolone systems under oxidative and reductive conditions
  作者：Yazmin M. Osornio、Luis D. Miranda、Raymundo Cruz-Almanza、Joseph M. Muchowski

  DOI：10.1016/j.tetlet.2004.01.123

  日期：2004.3

  Radical cyclizations to quinolone and isoquinolone systems under Fenton-type and n-Bu3SnH-mediated conditions are described. For N-iodoalkylquinolones, ca. 3:1 mixtures of oxidative cyclization products at C-2, and unexpectedly at C-8, were obtained under both conditions. Five- or six-membered oxidative cyclization products were obtained from N-iodoalkylisoquinolones under Fenton-type conditions, whereas

  描述了在芬顿型和n -Bu 3 SnH介导的条件下自由基环化成喹诺酮和异喹诺酮系统。对于N-碘代烷基喹诺酮，约。在两种条件下，均在C-2和C-8处意外获得了3：1的氧化环化产物混合物。在Fenton型条件下，从N-碘烷基异喹啉酮获得五或六元氧化环化产物，而n -Bu 3 SnH介导的反应在五元，六元和七元系列中得到还原环化产物。
• Deacylation-aided C–H alkylative annulation through C–C cleavage of unstrained ketones
  作者：Xukai Zhou、Yan Xu、Guangbin Dong

  DOI：10.1038/s41929-021-00661-7

  日期：——

  on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C–H annulation with diverse aromatic rings.

  芳烃和杂芳烃稠合环普遍存在于生物活性分子中。芳香核心上的 C-H 键和连接的烷基部分之间的直接环化提供了一种直接接近这些支架的方法；然而，这种策略通常会因需要特殊的反应基团和/或不太相容的环化条件而受到阻碍。如果可以使用一个共同的天然官能团作为手柄来实现具有不同芳香环的通用 C-H 环化，那将具有综合吸引力。在这里，我们展示了一种脱酰基环化策略，用于从线性简单酮前体制备多种芳族稠环。该反应首先通过前芳族中间体均裂酮α C-C 键，然后是自由基介导的脱氢环化。
• Short Approach Towards New Isocoumarins and Dihydroisocoumarins and Investigation of their Cytotoxic Activities
  作者：Isolde Wetzel、Franz Bracher、Jürgen Krauss

  DOI：10.1515/znb-2009-0310

  日期：2009.3.1

  3-Substituted isocoumarins were prepared in a short and efficient way from 2-iodobenzoic acid and terminal alkynes in a one-pot Sonogashira reaction. Catalytic hydrogenation gave the corresponding dihydroisocoumarins. The cytotoxic activities of the resulting compounds against human leukaemia cell line (HL 60) were determined in a MTT assay, and structure-activity relationships are discussed. Graphical

  3-取代的异香豆素是由 2-碘苯甲酸和末端炔烃在一锅 Sonogashira 反应中以一种简短有效的方式制备的。催化氢化得到相应的二氢异香豆素。在 MTT 试验中测定了所得化合物对人白血病细胞系 (HL 60) 的细胞毒活性，并讨论了结构-活性关系。新异香豆素和二氢异香豆素的图形摘要简短方法及其细胞毒活性研究
• Amidine and isothiourea derivatives as inhibitors of nitric oxide
  申请人：Astra Aktiebolag

  公开号：US06140322A1

  公开（公告）日：2000-10-31

  There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.

  提供了式(I)的新化合物：##STR1## 其中X，R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5如规范中所定义，以及其光学异构体和外消旋体以及其药学上可接受的盐；以及它们的制备过程，含有它们的组合物以及它们在治疗中的用途。