1-Cyano-2-(2-methylbenzoyl)-1,2-dihydroisochinolin | 30044-71-4

• 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-Cyano-2-(2-methylbenzoyl)-1,2-dihydroisochinolin
• 英文别名: 2-o-toluyl-1,2-dihydroisoquinaldonitrile；2-(2-methyl-benzoyl)-1,2-dihydro-isoquinoline-1-carbonitrile；2-(o-Methyl-benzoyl)-1,2-dihydro-isochinaldonitril；2-(2-methylbenzoyl)-1H-isoquinoline-1-carbonitrile
• CAS: 30044-71-4
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: MLDNOKWPIQKRFL-UHFFFAOYSA-N

物化性质

• 沸点：
  534.2±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

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：

  1-Cyano-2-(2-methylbenzoyl)-1,2-dihydroisochinolin 在 二硫化碳 、 sodium hydride 、 重水 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  The stereochemistry of isoquinoline Reissert compounds: a unique platform for observation of steric and electronic interactions

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.06.008
• 作为产物：
  描述：

  异喹啉 、 氰化钾 、 邻甲基苯甲酰氯 在 苄基三甲基氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以84%的产率得到1-Cyano-2-(2-methylbenzoyl)-1,2-dihydroisochinolin
  参考文献：
  名称：

  Reimann, Eberhard; Erdle, Wolfgang; Weigl, Claudia, Monatshefte fur Chemie, 1999, vol. 130, # 2, p. 313 - 326

  摘要：

  DOI：

文献信息

• Heterocyclic monomers via reissert chemistry
  作者：Harry W. Gibson、Melvin L. Rasco、Zhenbin Niu

  DOI：10.1002/pola.24821

  日期：2011.9.1

  fluoro‐phenolic monomer (14), and an AB2 alcohol‐diester monomer precursor (17), all based on the isoquinoline nucleus, were prepared using Reissert compound chemistry. Additionally, model reactions established the efficiency of condensation of isoquinoline Reissert compounds with dihaloalkanes, providing evidence of the potential of this reaction to produce high molecular weight polymers, which was subsequently

  使用Reissert化合物化学方法制备了均基于异喹啉核的AA双酚类单体（13），AB活化的氟酚类单体（14）和AB 2醇二酯单体前体（17）。此外，模型反应确定了异喹啉Reissert化合物与二卤代烷烃缩合的效率，为该反应潜在地生产高分子量聚合物提供了证据，这一点随后得以实现。©2011 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2011年