3-Iodo-5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indazole | 290368-01-3

• 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: 3-Iodo-5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indazole
• 英文别名: 3-iodo-5-methoxy-1-(4-methylphenyl)sulfonylindazole
• CAS: 290368-01-3
• 化学式: C₁₅H₁₃IN₂O₃S
• 分子量: 428.25
• InChiKey: OTUBXPAYDLXMMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙烯酸甲酯（MA） 、 3-Iodo-5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indazole 在 palladium diacetate 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以20%的产率得到methyl (E)-3-[5-methoxy-1-(4-methylphenyl)sulfonylindazol-3-yl]prop-2-enoate
  参考文献：
  名称：

  Heck cross-coupling reaction of 3-iodoindazoles with methyl acrylate: a mild and flexible strategy to design 2-aza tryptamines

  摘要：

  In order to design 2-azabioisosteres of tryptamine, serotonin or melatonin, the conditions of the Heck coupling reaction of 3-iodoindazoles with methyl acrylate are studied. This reaction authorizes the synthesis of 3-indazolylpropenoates as key intermediates to prepare 3-indazolylpropionic acids and 3-indazolylethyl-amines. The flexible synthetic strategy allows molecular diversity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00624-9
• 作为产物：
  描述：

  5-甲氧基-1H-吲唑 在 氢氧化钾 、 potassium tert-butylate 、 碘 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-Iodo-5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indazole
  参考文献：
  名称：

  Heck cross-coupling reaction of 3-iodoindazoles with methyl acrylate: a mild and flexible strategy to design 2-aza tryptamines

  摘要：

  In order to design 2-azabioisosteres of tryptamine, serotonin or melatonin, the conditions of the Heck coupling reaction of 3-iodoindazoles with methyl acrylate are studied. This reaction authorizes the synthesis of 3-indazolylpropenoates as key intermediates to prepare 3-indazolylpropionic acids and 3-indazolylethyl-amines. The flexible synthetic strategy allows molecular diversity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00624-9

文献信息

• Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: a mild and flexible strategy to design 2-aza tryptamines
  作者：Anca Arnautu、Valérie Collot、Javier Calvo Ros、Carole Alayrac、Bernhard Witulski、Sylvain Rault

  DOI：10.1016/s0040-4039(02)00393-3

  日期：2002.4

  This paper describes a Sonogashira-type cross-coupling reaction of 3-iodoindazoles various terminal alkynes as a general route to 3-alkynylindazoles. The Coupling reaction is illustrated by the preparation of ne indazolylpropiolic or propargylic derivatives. Scope and limitation of the method are outlined. (C) 2002 Elsevier Science Ltd. All rights reserved.