methyl 4-methoxy-2-(1-propynyl)benzoate | 315179-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-methoxy-2-(1-propynyl)benzoate
• 英文别名: Methyl 4-methoxy-2-prop-1-ynylbenzoate
• CAS: 315179-92-1
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: IGUQGNRXPCPWBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-methoxy-2-(1-propynyl)benzoate 在 lithium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲醇 、 水 、 xylene 、 苯 为溶剂， 反应 30.5h， 生成
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e
• 作为产物：
  描述：

  4-甲氧基水杨酸甲酯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 4-methoxy-2-(1-propynyl)benzoate
  参考文献：
  名称：

  Synthesis of 6H-Indolo[2,3-b][1,6]naphthyridines and Related Compounds as the 5-Aza Analogues of Ellipticine Alkaloids

  摘要：

  Treatment of 2-(1-alkynyl)phenyl isocyanates 6 with the iminophosphorane 14 produced in situ the benzoenynyl carbodiimides 15. Thermolysis of 15 under refluxing p-xylene furnished the 6H-indolo[2,3-b][1,6]naphthyridines 5, which could be regarded as the 5-aza analogues of ellipticine alkaloids. Similarly,condensation of 6 with the iminophosphorane 20 led to the formation of the 6H-indolo[2,3-b][1,5]naphthyridines 25 as the major isomer and the 10H- indolo[2,3-b][1,7]-naphthyridines 26 as the minor isomer. The indolonaphthyridines 32, 33, and 34 having a methoxyl substituent were likewise synthesized. Treatment of the diisocyanate 43 with 2 equiv of the iminophosphorane 7 furnished 45 having two indoloquinoline units incorporated in a seven-fused-ring system.

  DOI：

  10.1021/jo000978e

文献信息

• Indium-mediated Palladium-catalyzed Allylic Alkylation of Isatins with Alkynes
  作者：Zijun Wu、Xinxin Fang、Yuning Leng、Hequan Yao、Aijun Lin

  DOI：10.1002/adsc.201701139

  日期：2018.3.20

  An unprecedented indium‐mediated palladium‐catalyzed allylic alkylation of isatins with alkynes is disclosed. This reaction provides a new, practical, and straightforward route to access 3‐allyl‐3‐hydroxy‐2‐oxindoles in good yields with broad substrate scope and scalability, exhibiting high atom and step economy. A primary mechanistic study reveals that indium played two roles in the reaction, first

  公开了前所未有的铟介导的钯催化炔烃与钯的烯丙基烷基化反应。该反应提供了一种新的，实用的，直接的途径，以高收率获得3-烯丙基-3-羟基-2-氧吲哚，具有广泛的底物范围和可扩展性，具有很高的原子和步骤经济性。初步的机理研究表明，铟在反应中起着两个作用，首先是还原剂，其次是路易斯酸。与以前的方法相比，我们的策略省去了分离和纯化反应中间体的步骤，以及将离去基团预先安装在烯丙基底物上的步骤。此外，我们的反应未使用对水分敏感的烯丙基金属物质和化学计量的氧化剂。