(+/-)-acetic acid 1-(isoquinolin-3-yl)ethyl ester | 58793-98-9

• 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: (+/-)-acetic acid 1-(isoquinolin-3-yl)ethyl ester
• 英文别名: 1-acetoxy-1-isoquinolin-3-yl-ethane；1-(3-Isochinolinyl)-ethylacetat；1-Isoquinolin-3-ylethyl acetate
• CAS: 58793-98-9
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: FMALANGQUMIFIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±17.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-acetic acid 1-(isoquinolin-3-yl)ethyl ester 在 4-二甲氨基吡啶 、 phosphate buffer 、 lipase from Candida antarctica 作用下， 以 二氯甲烷 、 异丙醚 、 水 为溶剂， 反应 21.25h， 生成
  参考文献：
  名称：

  Homochiral isoquinolines by lipase-catalysed resolution and their diastereoselective functionalisation

  摘要：

  Kinetic resolution of racemic isoquinoline alcohols and acetates has been successfully accomplished using lipases as chiral catalysts, The diastereoselective functionalisation of the isoquinoline moiety through the addition of C-nucleophiles to O-protected alcohol 9a in the presence of phenyl chloroformate has been carried out and dihydroquinolyl alcohol derivatives with high diastereomeric excess have been prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00178-1
• 作为产物：
  描述：

  2-(1,3-dioxolan-2-yl)benzaldehyde 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium azide 、 三甲基铝 、 三乙胺 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 5.5h， 生成 (+/-)-acetic acid 1-(isoquinolin-3-yl)ethyl ester
  参考文献：
  名称：

  Homochiral isoquinolines by lipase-catalysed resolution and their diastereoselective functionalisation

  摘要：

  Kinetic resolution of racemic isoquinoline alcohols and acetates has been successfully accomplished using lipases as chiral catalysts, The diastereoselective functionalisation of the isoquinoline moiety through the addition of C-nucleophiles to O-protected alcohol 9a in the presence of phenyl chloroformate has been carried out and dihydroquinolyl alcohol derivatives with high diastereomeric excess have been prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00178-1

文献信息

• Reactivity of Quinoline- and Isoquinoline-Based Heteroaromatic Substrates in Palladium(0)-Catalyzed Benzylic Nucleophilic Substitution
  作者：Jean-Yves Legros、Gaëlle Primault、Martial Toffano、Marie-Alix Rivière、Jean-Claude Fiaud

  DOI：10.1021/ol991274y

  日期：2000.2.1

  dimethylmalonate anion in the presence of a Pd(0) catalyst to give products of nucleophilic substitution and/or byproducts, depending upon the substitution pattern. The observed side reactions were reduction in the case of primary acetates and elimination or elimination/Michael-type addition sequence for secondary substrates.

  [反应：参见正文]在Pd（0）催化剂存在下，喹啉基甲基，1-（异喹啉基）乙基和1-（喹啉基）乙基乙酸酯与丙二酸二甲酯阴离子反应生成亲核取代产物和/或副产物，具体取决于替代模式。观察到的副反应是在初级乙酸盐的情况下还原，以及消除或消除了次要底物的Michael-型添加顺序。
• JPS54138575A
  申请人：——

  公开号：JPS54138575A

  公开（公告）日：1979-10-27
• Homochiral isoquinolines by lipase-catalysed resolution and their diastereoselective functionalisation
  作者：Giuseppe Guanti、Renata Riva

  DOI：10.1016/s0957-4166(01)00178-1

  日期：2001.5

  Kinetic resolution of racemic isoquinoline alcohols and acetates has been successfully accomplished using lipases as chiral catalysts, The diastereoselective functionalisation of the isoquinoline moiety through the addition of C-nucleophiles to O-protected alcohol 9a in the presence of phenyl chloroformate has been carried out and dihydroquinolyl alcohol derivatives with high diastereomeric excess have been prepared. (C) 2001 Elsevier Science Ltd. All rights reserved.