3-碘-1-甲苯磺酰-1H-吲哚-2-甲醛 | 233770-15-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-碘-1-甲苯磺酰-1H-吲哚-2-甲醛
• 英文名称: 2-formyl-3-iodo-1-tosylpyrrole
• 英文别名: 3-Iodo-1-(4-methylphenyl)sulfonylpyrrole-2-carbaldehyde
• CAS: 233770-15-5
• 化学式: C₁₂H₁₀INO₃S
• 分子量: 375.187
• InChiKey: NDAZPULNWLUXRY-UHFFFAOYSA-N

物化性质

• 沸点：
  504.1±60.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-碘-1-甲苯磺酰-1H-吲哚-2-甲醛 在 potassium permanganate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以40%的产率得到3-iodo-2-formylpyrrole
  参考文献：
  名称：

  Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues

  摘要：

  铜促进3-吡咯硼酸衍生物与卤代芳香烃的Suzuki交叉偶联反应，以及反向过程即3-碘(溴)吡咯烷与芳基硼酸的偶联反应已被研究作为合成(–)-拉洁嗪和类似物的潜在关键步骤。发现3-碘-2-甲酰基-1-对甲苯磺酰基吡咯烷在PdCl₂(dppf)催化剂存在下有效地与各种芳基硼酸偶联。该催化系统与广泛的芳基硼酸兼容，包括富电子、贫电子、障碍、杂环化合物，这些都可以轻松地与吡咯底物偶联。关键词：2-取代-3-芳基吡咯、联苯、偶联反应、芳基硼酸、钯偶联、催化。

  DOI：

  10.1139/v01-156
• 作为产物：
  描述：

  苯磺酰胺,4-甲基-N-(3-苯基-2-亚丙烯基)-,(E,E)- 在 potassium permanganate 、 正丁基锂 、 氢碘酸 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 3-碘-1-甲苯磺酰-1H-吲哚-2-甲醛
  参考文献：
  名称：

  A general synthesis of 2-formyl-3-arylpyrroles

  摘要：

  2-Formyl-3-iodo-1 -tosylpyrrole 2 has been prepared in four steps from cinnamaldehyde. It was coupled with a wide variety of arylboronic acids to give the corresponding biaryl compounds in high yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00808-4

文献信息

• Synthesis of 4-Vinylindoles Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
  作者：Kazushi Hayashi、Kazuhiro Yoshida、Akira Yanagisawa

  DOI：10.1021/jo400099x

  日期：2013.4.5

  The selective synthesis of substituted 4-vinylindoles by the ring-closing enyne metathesis (RCEM)/dehydration sequence is reported. In contrast with many known methods in which a pyrrole ring is constructed onto a functionalized benzene precursor, this method enables the construction of a benzene ring onto a pyrrole precursor. The RCEM/tautomerization sequence for the synthesis of 7-hydroxy-4-vinylindole is also presented as an application of this method.
• A general synthesis of 2-formyl-3-arylpyrroles
  作者：Cécile Franc、Frédéric Denonne、Claire Cuisinier、Léon Ghose

  DOI：10.1016/s0040-4039(99)00808-4

  日期：1999.6

  2-Formyl-3-iodo-1 -tosylpyrrole 2 has been prepared in four steps from cinnamaldehyde. It was coupled with a wide variety of arylboronic acids to give the corresponding biaryl compounds in high yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Studies of palladium-catalyzed coupling reactions for preparation of hindered 3-arylpyrroles relevant to (-)-rhazinilam and its analogues
  作者：Léon Ghosez、Cécile Franc、Frédéric Denonne、Claire Cuisinier、Roland Touillaux

  DOI：10.1139/v01-156

  日期：2001.11.1

  Suzuki cross-coupling reactions of 3-pyrroleboronic acid derivatives with haloaromatics and the reverse process i.e., the coupling of 3-iodo(bromo)pyrroles with arylboronic acids have been investigated as a potential key step in the synthesis of (–)-rhazinilam and analogues. It was found that 3-iodo-2-formyl-1-tosylpyrroles efficiently coupled with a variety of arylboronic acids in the presence of PdCl₂(dppf) as catalyst. This catalytic system is compatible with a broad spectrum of arylboronic acids — electron-rich, electron-poor, hindered, heterocyclic — which easily coupled with the pyrrole substrate.Key words: 2-substituted-3-arylpyrroles, biaryls, coupling reactions, arylboronic acids, palladium coupling, catalysis.

  铜促进3-吡咯硼酸衍生物与卤代芳香烃的Suzuki交叉偶联反应，以及反向过程即3-碘(溴)吡咯烷与芳基硼酸的偶联反应已被研究作为合成(–)-拉洁嗪和类似物的潜在关键步骤。发现3-碘-2-甲酰基-1-对甲苯磺酰基吡咯烷在PdCl₂(dppf)催化剂存在下有效地与各种芳基硼酸偶联。该催化系统与广泛的芳基硼酸兼容，包括富电子、贫电子、障碍、杂环化合物，这些都可以轻松地与吡咯底物偶联。关键词：2-取代-3-芳基吡咯、联苯、偶联反应、芳基硼酸、钯偶联、催化。