| 1394079-89-0

• 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
• CAS: 1394079-89-0
• 化学式: C₁₇H₁₂N₂O
• 分子量: 261.287
• InChiKey: HIRCCKPODGFADB-QNLPYAOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.1
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-苯甲酰基-1-氰基-1,2-二氢异喹啉 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， 反应 0.75h， 以92%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