1,2-Dihydro-3H,5H-pyrrolo<1,2-b>isoquinoline-5-one | 76352-37-9

• 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: 1,2-Dihydro-3H,5H-pyrrolo<1,2-b>isoquinoline-5-one
• 英文别名: 5-oxo-1,2,3,5-tetrahydropyrrolo<1,2-b>isoquinoline；2,3-Dihydropyrrolo<1,2-b>isoquinolin-5(1H)-one；2,3-dihydropyrrolo<1,2-b>isoquinolin-5(1H)one；2,3-dihydropyrrolo[1,2-b]isoquinolin-5(1H)-one；2,3-dihydro-1H-pyrrolo[1,2-b]isoquinolin-5-one
• CAS: 76352-37-9
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: JHGCHPYSTQDNRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C
• 沸点：
  373.6±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-Dihydro-3H,5H-pyrrolo<1,2-b>isoquinoline-5-one 在 selenium(IV) oxide 、 lithium carbonate 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 水 、 二氯甲烷 为溶剂， 反应 24.0h， 以58%的产率得到2,3-dihydropyrrolo[1,2-b]isoquinoline-1,5-dione
  参考文献：
  名称：

  一种通用的Cp * CoIII催化的分子内C-H活化方法，可有效地合成香霉素，原小T碱和触毛生物碱

  摘要：

  在此，我们报告Cp * Co III催化的C H活化方法是创建高度有价值的异喹诺酮和吡啶酮的重要步骤，这些异喹啉酮和吡啶酮可以轻松地用于各种芳香族素，原小ber碱和tylophora生物碱的总合成。这种特殊的CH活化/环化反应是通过多个末端以及内部炔烃偶联伙伴实现的，具有广泛的应用范围和出色的官能团耐受性。本文报道的该方案的合成适用性已在两个Topo-I-抑制剂和两个8-氧代小ber碱核心的合成中得到了证明，这些核心可进一步制成四氢小ber碱和原小ber碱生物碱。此外，这些构件也以方便的方式转化为六种不同的tylophora生物碱。

  DOI：

  10.1002/chem.201702648
• 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 12.83h， 生成 1,2-Dihydro-3H,5H-pyrrolo<1,2-b>isoquinoline-5-one
  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

• Rhodium(III)-Catalyzed Intramolecular Annulation through CH Activation: Total Synthesis of (±)-Antofine, (±)-Septicine, (±)-Tylophorine, and Rosettacin
  作者：Xianxiu Xu、Yu Liu、Cheol-Min Park

  DOI：10.1002/anie.201204970

  日期：2012.9.10

  Annulation: The efficient synthesis of 3‐hydroxyalkyl isoquinolones and 6‐hydroxyalkyl 2‐pyridones is enabled through the intramolecular annulation of alkyne‐tethered hydroxamic esters (see scheme, Cp*=pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional‐group tolerance, proceeds under mild reaction conditions with low catalyst loading

  注释：通过炔烃系异羟肟酸酯的分子内环化，可实现3-羟基烷基异喹诺酮和6-羟基烷基2-吡啶酮的高效合成（参见方案，Cp * =五甲基环戊二烯基）。该反应具有较高的区域选择性，广泛的底物范围和出色的官能团耐受性，可在温和的反应条件下以较低的催化剂负载量进行，并且无需外部氧化剂。
• Catalytic Intramolecular Wittig Reaction Based on a Phosphine/Phosphine Oxide Catalytic Cycle for the Synthesis of Heterocycles
  作者：Long Wang、Mei Sun、Ming-Wu Ding

  DOI：10.1002/ejoc.201601628

  日期：2017.5.10

  The catalytic intramolecular Wittig reactions of carbonyl-containing bromides are reported. The R3PO byproducts participate in the catalytic cycle; therefore, the Wittig reaction can be accomplished with only a catalytic amount of organophosphorus reagent. The reaction has also been applied to the efficient and selective synthesis of isoquinolin-1(2H)-ones, indoles, 2,3-dihydro-1H-2-benzazepin-1-ones

  报道了含羰基溴化物的催化分子内 Wittig 反应。R3PO 副产物参与催化循环；因此，只需使用催化量的有机磷试剂即可完成 Wittig 反应。该反应也已应用于异喹啉-1(2H)-酮、吲哚、2,3-二氢-1H-2-苯并氮杂-1-酮、苯并呋喃和 1,2-二氢喹啉的高效和选择性合成催化量的氧化膦（0.1 当量）和四甲基二硅氧烷/异丙醇钛 [TMDS/Ti(OiPr)4] 还原剂系统（产率：35-88%）。
• 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。
• Amidine and isothiourea derivatives, compositions containing them and
  申请人：Astra Aktiebolag

  公开号：US05929085A1

  公开（公告）日：1999-07-27

  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。
• Dinoflagellate bioluminescence: Chemical behavior of the chromophore towards oxidants
  作者：Milan N. Stojanovic、Yoshito Kishi

  DOI：10.1016/s0040-4039(00)78539-x

  日期：1994.12

  chromophore model 5 of dinoflagellate luciferin was synthesized, and its behavior towards oxidants was studied. Molecular oxygen at high substrate concentrations, superoxide anion, and Fenton reagent effected oxidation of 5 at the C.132 position. On the basis of these results, a possible mechanism for these oxidations and for bioluminescent air-oxidation of dinoflagellate luciferin, is suggested.

  合成了鞭毛萤光素的发色团模型5，并研究了其对氧化剂的行为。高底物浓度的分子氧，超氧阴离子和Fenton试剂在C.13 2位置氧化5。基于这些结果，提出了可能的机制，用于二鞭毛萤光素荧光素的这些氧化和生物发光空气氧化。