toluene-4-sulfonic acid-3-(1-methylindol-3-yl)propyl ester | 127561-72-2

• 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: toluene-4-sulfonic acid-3-(1-methylindol-3-yl)propyl ester
• 英文别名: 1-Methyl-3-(3-p-toluenesulfonyloxypropyl)indole；3-(1-Methylindol-3-yl)propyl 4-methylbenzenesulfonate
• CAS: 127561-72-2
• 化学式: C₁₉H₂₁NO₃S
• 分子量: 343.447
• InChiKey: NGUXIXBPKOCSIS-UHFFFAOYSA-N

物化性质

• 沸点：
  538.3±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid-3-(1-methylindol-3-yl)propyl ester 在 氧气 palladium diacetate 、 频哪酮 、 烟酸乙酯 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 23.0~80.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 rac-1,9-dimethyl-1-vinyl-2,3,4,9-tetrahydrocarbazole
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y
• 作为产物：
  描述：

  3-(1-methylindol-3-yl)propionaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 toluene-4-sulfonic acid-3-(1-methylindol-3-yl)propyl ester
  参考文献：
  名称：

  Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles

  摘要：

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.

  DOI：

  10.1021/ja035054y

文献信息

• Enantioselective Fujiwara-Moritani Indole and Pyrrole Annulations Catalyzed by Chiral Palladium(II)-NicOx Complexes
  作者：Julia A. Schiffner、Thorsten H. Wöste、Martin Oestreich

  DOI：10.1002/ejoc.200901129

  日期：2010.1

  catalytic asymmetric Fujiwara-Moritani ring closures of several indole- and pyrrole-based cyclization precursors are reported. These unprecedented oxidative palladium(II)-catalyzed annulations allow for the formation of a stereogenic quaternary carbon atom, and decent levels of enantiocontrol are seen in 5-exo-trig cyclizations (54 % ee for an indole and 76 % ee for a pyrrole) while 6-exo-trig ring

  报道了几种基于吲哚和吡咯的环化前体的催化不对称 Fujiwara-Moritani 闭环。这些前所未有的氧化钯 (II) 催化环化允许形成立体季碳原子，并且在 5-exo-trig 环化（吲哚 54 % ee 和吡咯 76 % ee）中看到了相当水平的对映控制而 6-exo-trig 闭环提供了基本上外消旋的材料。具有尼古丁平台 (NicOx) 的新型恶唑啉配体对于良好的催化转化至关重要，因为传统的 PyOx 配体无法产生可接受的化学产率。详细描述了这些 NicOx 配体的制备以及环化前体的合成。
• 1-Indolylalkyl-4-(alkoxy-pyrimidinyl)piperazines
  申请人：Bristol-Myers Squibb Company

  公开号：EP0464604A2

  公开（公告）日：1992-01-08

  Certain 1-indolylalkyl-4-(alkoxypyrimidinyl) piperazines are useful antidepressant compounds.

  某些 1-吲哚烷基-4-(烷氧基嘧啶基)哌嗪是有用的抗抑郁化合物。
• US5077293A
  申请人：——

  公开号：US5077293A

  公开（公告）日：1991-12-31
• Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles
  作者：Eric M. Ferreira、Brian M. Stoltz

  DOI：10.1021/ja035054y

  日期：2003.8.1

  A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C-H bond activation) followed by migratory insertion and beta-hydrogen elimination.