2,3-dipropyl-1-tosylindole | 135189-94-5

• 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: 2,3-dipropyl-1-tosylindole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2,3-dipropylindole；1-(4-methylphenyl)sulfonyl-2,3-dipropylindole
• CAS: 135189-94-5
• 化学式: C₂₁H₂₅NO₂S
• 分子量: 355.501
• InChiKey: HNAPELHNBHHHGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-辛炔 、 N-对甲苯磺酰基-2-碘苯胺 在 palladium 10% on activated carbon 、 sodium acetate 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 7.0h， 以96%的产率得到2,3-dipropyl-1-tosylindole
  参考文献：
  名称：

  非均相条件下钯/碳催化2-和2,3-取代的吲哚的合成†

  摘要：

  一种温和，高效且不含LiCl的合成方法 吲哚 基于炔烃与2-碘苯胺杂环化的衍生物是使用 钯 在 碳 （钯/C） 和 醋酸钠 在加热 NMP。这N-甲苯磺酰基 保护 2-碘苯胺加快了反应的进程，而其他保护基团，例如叔丁氧羰基，乙酰基和苄氧羰基，在当前条件下进行了脱保护。各种二和单取代的炔烃可以有效地与N-甲苯磺酰基-2-碘苯胺 使相应的吲哚获得高到高的收率。

  DOI：

  10.1039/c004939e

文献信息

• Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes
  作者：R. C. Larock、E. K. Yum、M. D. Refvik

  DOI：10.1021/jo9803277

  日期：1998.10.1

  The palladium-catalyzed coupling of 2-iodoaniline and the corresponding N-methyl, -acetyl, and -tosyl derivatives with a wide variety of internal alkynes provides 2,3-disubstituted indoles in good-to-excellent yields. The best results are obtained by employing an excess of the alkyne and a sodium or potassium acetate or carbonate base plus 1 equiv of either LiCl or n-Bu4NCl, occasionally adding 5 mol % PPh3. The yields with LiCl appear to be higher and more reproducible than those obtained with n-Bu4NCl. The process is quite general as far as the types of substituents which can be accommodated on the nitrogen of the aniline and the two ends of the alkyne triple bond. The reaction is quite regioselective, placing the aryl group of the aniline on the less sterically hindered end of the triple bond and the nitrogen moiety on the more sterically hindered end. This methodology readily affords 2-silylindoles, which can be easily protodesilylated, halogenated, or reacted with alkenes and Pd(OAc)(2) to produce 3-substituted indoles, 2-haloindoles, or 2-(1-alkenyl)indoles, respectively. The presence of alcohol groups in the alkyne seems to have a particularly strong directing effect, perhaps due to coordination with palladium. This catalytic process apparently involves arylpalladium formation, regioselective addition to the C-C triple bond of the alkyne, and subsequent intramolecular palladium displacement.
• Larock, Richard C.; Yum, Eul Kgun, Journal of the American Chemical Society, 1991, vol. 113, # 17, p. 6689 - 6690
  作者：Larock, Richard C.、Yum, Eul Kgun

  DOI：——

  日期：——
• Palladium on carbon-catalyzed synthesis of 2- and 2,3-substituted indoles under heterogeneous conditions
  作者：Yasunari Monguchi、Shigeki Mori、Satoka Aoyagi、Azusa Tsutsui、Tomohiro Maegawa、Hironao Sajiki

  DOI：10.1039/c004939e

  日期：——

  A mild, efficient and LiCl-free synthetic method for indole derivatives based on the heteroannulation of alkynes with 2-iodoanilines was achieved using palladium on carbon (Pd/C) and NaOAc in heated NMP. The N-tosyl protection of 2-iodoaniline expedited the reaction progress, while other protecting groups, such as tert-butoxycarbonyl, acetyl, and benzyloxycarbonyl groups, underwent deprotection under

  一种温和，高效且不含LiCl的合成方法 吲哚 基于炔烃与2-碘苯胺杂环化的衍生物是使用 钯 在 碳 （钯/C） 和 醋酸钠 在加热 NMP。这N-甲苯磺酰基 保护 2-碘苯胺加快了反应的进程，而其他保护基团，例如叔丁氧羰基，乙酰基和苄氧羰基，在当前条件下进行了脱保护。各种二和单取代的炔烃可以有效地与N-甲苯磺酰基-2-碘苯胺 使相应的吲哚获得高到高的收率。