2-苯甲酰基-3-甲基-1H-异喹啉-1-腈 | 21259-77-8

• 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: 2-苯甲酰基-3-甲基-1H-异喹啉-1-腈
• 英文名称: 2-benzoyl-3-methyl-1,2-dihydroisoquinoline-1-carbonitrile
• 英文别名: 3-methylisoquinoline Reissert compound；2-benzoyl-3-methyl-1,2-dihydro-isoquinoline-1-carbonitrile；2-Benzoyl-3-methyl-1,2-dihydro-isochinolin-1-carbonitril；2-benzoyl-3-methyl-1H-isoquinoline-1-carbonitrile
• CAS: 21259-77-8
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: XZDFOLUDAFZNQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苯甲酰基-3-甲基-1H-异喹啉-1-腈 在 氢氧化钾 、 苄基三乙基氯化铵 、 邻羧基苯甲醛 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (3-methylisoquinolin-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Central nervous system active compounds. VI. Reissert compounds as precursors of 1-(3-phthalidy1)isoquinolines

  摘要：

  异喹啉和酞嗪 异喹啉和酞嗪 Reissert 化合物与邻苯二甲酸及其衍生物的反应，作为合成 1-(3-邻苯二甲酸基)异喹啉的方法进行了研究。 作为合成 1-(3-酞酰基)异喹啉的一种方法进行了研究。在尝试的各种条件中 发现涉及相转移的条件一般最合适。其 产品是惊厥碱的类似物 生物碱的类似物，显示出微弱的中枢神经系统抑制活性。 系统抑制活性。

  DOI：

  10.1071/ch9810151
• 作为产物：
  描述：

  3-甲基异喹啉 、 氰化钾 、 苯甲酰氯 在 水 作用下， 生成 2-苯甲酰基-3-甲基-1H-异喹啉-1-腈
  参考文献：
  名称：

  Nature of the Organic Base in Reissert Compounds¹

  摘要：

  DOI：

  10.1021/ja01621a067

文献信息

• Potential anticonvulsants. X. (Reissert compounds studies. LI.) 1-methyl-4-(1-isoquinolinyl)piperidin-4-ol and related compounds
  作者：Frank D. Popp、Joydeep Kant

  DOI：10.1002/jhet.5570220353

  日期：1985.5

  The anion of isoquinoline Reissert Compounds has been condensed with 4-piperidones and pyridinecarb-oxaldehydes to give esters which are easily hydrolyzed to alcohols. The anticonvulsants activity of these alcohols is reported and several are active in the maximal electroshock seizure test.

  异喹啉Reissert化合物的阴离子已与4-哌啶酮和吡啶碳基-甲醛醛缩合，生成易于水解为醇的酯。据报道这些醇的抗惊厥活性，并且在最大的电击惊厥试验中有几种具有活性。
• Synthesis of 6-methyl-8H-dibenzo[a,g]quinolizin-8-imines via Reissert compounds
  作者：Eberhard Reimann、Rainer Hertel、Jürgen Krauss

  DOI：10.1007/s00706-007-0826-8

  日期：2008.6

  Alkylation of Reissert compounds derived from 3-methylisoquinolines with several 2-cyanobenzylbromides followed by hydrolytic cleavage provided the corresponding 1-benzyl-3-methylisoquinolines. Treatment of the latter with methylmagnesiumiodide caused cyclization to the title compounds rather than formation of 2-acetylbenzylisoquinolines.

  衍生自3-甲基异喹啉的 Reissert化合物与几种2-氰基苄基溴化物进行 烷基化， 然后进行水解裂解，得到相应的1-苄基-3-甲基异喹啉。用甲基碘化镁处理后者会引起标题化合物的环化，而不是形成2-乙酰基苄基异喹啉。
• The stereochemistry of isoquinoline Reissert compounds: a unique platform for observation of steric and electronic interactions
  作者：Harry W. Gibson、Michael A.G. Berg、Terry L. Price、Zhenbin Niu、Minjae Lee、Mason A. Rouser、Jennifer Clifton Dickson、Carla Slebodnick

  DOI：10.1016/j.tet.2012.06.008

  日期：2012.9

  Isoquinoline Reissert compounds (2-acyl-1,2-dihydroisoquinaldonitriles) with either 3-H (1) or 3-CH3 (2) substituents and various N-acyl groups have been examined in detail by H-1 and C-13 NMR spectroscopy and X-ray crystallography. In all cases the trans amide conformation, with reference to the carbonyl oxygen and the 3-position of the isoquinoline ring, predominates in solution. In the solid state the nitrite moieties are pseudo-axial and the amides exist almost exclusively in the trans form, except for the case of 2-isobutyryl-3-methyl-1,2-dihydroisoquinaldonitrile (2c), which exists exclusively as the cis amide form in the solid state. In N-aroyl 3-CH3 compounds with two ortho-aroyl substituents both amide isomerism and hindered aryl/carbonyl rotation are observed by H-1 NMR spectroscopy. In other N-aroyl derivatives only hindered aryl/carbonyl rotations are observed by NMR and in N-alkanoyl compounds amide isomerism is observable only at very low temperatures. X-ray crystallography reveals the two rotamers in the solid state in four cases of ortho-substituted benzoyl compounds; with one exception, the rotamer with the larger ortho-aroyl substituent syn to the pseudo-axial cyano group is favored. Unusual solubility and reactivity patterns observed with these compounds are rationalized in terms of the interplay between steric and electronic factors. (C) 2012 Elsevier Ltd. All rights reserved.
• KIRBY G. W.; MACKINNON J. W. M.; ELLIOT S.; UFF B. C., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 5, 1298-1302
  作者：KIRBY G. W.、 MACKINNON J. W. M.、 ELLIOT S.、 UFF B. C.

  DOI：——

  日期：——
• HUNG, TRAN, V.;MOONEY, B. A.;PRAGER, R. H.;WARD, A. D., AUSTRAL. J. CHEM., 1981, 34, N 1, 151-162
  作者：HUNG, TRAN, V.、MOONEY, B. A.、PRAGER, R. H.、WARD, A. D.

  DOI：——

  日期：——