1-(1-tosyl-1H-indol-3-yl)ethan-1-ol | 701204-62-8

• 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: 1-(1-tosyl-1H-indol-3-yl)ethan-1-ol
• 英文别名: 1-[1-(4-Methylphenyl)sulfonylindol-3-yl]ethanol
• CAS: 701204-62-8
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: IEYFVZNJXOCZIH-UHFFFAOYSA-N

物化性质

• 沸点：
  526.0±52.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-tosyl-1H-indol-3-yl)ethan-1-ol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 1H-吲哚,3-乙酰基-1-[(4-甲基苯基)磺酰]-
  参考文献：
  名称：

  Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

  摘要：

  A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

  DOI：

  10.1021/jacs.5b00613
• 作为产物：
  描述：

  1H-吲哚,3-乙酰基-1-[(4-甲基苯基)磺酰]- 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-(1-tosyl-1H-indol-3-yl)ethan-1-ol
  参考文献：
  名称：

  Mn(OAc) 3 ⋅2H 2 O促进的自由基加成和环化中继：1,2-氧杂磷代吲哚的合成及机理研究

  摘要：

  新型高效的 Mn(OAc) 3 ⋅2H 2 O 促进了 3-吲哚甲醇和亚磷酸酯的自由基加成-[4 + 1] 环化中继，以中等至良好的产率提供了 1,2-氧杂磷并吲哚衍生物。基于实验和计算研究，提出了一种涉及自由基加成和分子内环化级联的机制。

  DOI：

  10.1016/j.cclet.2021.02.001

文献信息

• [EN] N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM<br/>[FR] INDOLES N-ARYLSULFONYL-3-SUBSTITUES PRESENTANT UNE AFFINITE POUR LE RECEPTEUR DE LA SEROTONINE, METHODE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE CONTENANT CES INDOLES
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004048330A1

  公开（公告）日：2004-06-10

  The present invention relates to novel N-arylsulfonyl-3-substituted indole compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their geometric forms, their N-oxides, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel N-arylsulfonyl-3-substituted indoles of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, and pharmaceutically acceptable compositions containing them. This invention also relates to the process for preparing compounds of the general formula (I), pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine. This invention also relates to the novel intermediates involved therein and process of their preparation.

  本发明涉及新型的N-芳基亚磺酰基-3-取代吲哚化合物、其衍生物、类似物、互变异构体、立体异构体、几何异构体、N-氧化物、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明特别涉及具有通用公式(I)的新型N-芳基亚磺酰基-3-取代吲哚、其衍生物、类似物、互变异构体、立体异构体、多晶型、药物可接受的盐、药物可接受的溶剂化物以及含有它们的药物可接受组合物。本发明还涉及制备通用公式(I)化合物的过程、含有此类化合物的药物组合物以及此类化合物和组合物在医学中的用途。本发明还涉及其中涉及的新中间体及其制备过程。
• Unusual Formation of Cyclopenta[<i>b</i>]indoles from 3-Indolylmethanols and Alkynes
  作者：Soniya Gandhi、Beeraiah Baire

  DOI：10.1021/acs.joc.8b03027

  日期：2019.4.5

  suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening–ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene

  已经报道了由3-吲哚基甲醇和炔烃酸促进的环戊[ b ]吲哚骨架的合成。整个变换表示通过重新排列而形成的正式[3 + 2]圆环。该方案对甲醇底物和炔烃显示出良好的通用性，并允许生成结构多样的环戊[ b ]吲哚。发现末端炔烃，二烷基取代的内部炔烃和具有电子不足的取代基的炔烃不适合该转化。同样，N -Ts和N -Boc基团与反应条件兼容，而N -Ac和N-Tf未能进行此反应。氯乙烯中间体的分离表明涉及乙烯基碳阳离子中间体。已经提出了一种机制，包括开环-​​闭环级联反应，然后通过螺环丁烯中间体进行1,3-吲哚迁移过程。
• Heteroaromatic Decarboxylative Claisen Rearrangement Reactions
  作者：Donald Craig、N. Paul King、Jörg T. Kley、David M. Mountford

  DOI：10.1055/s-2005-918448

  日期：——

  pyrrol-2-ylmethyl tosylacetates undergo facile decarboxylative Claisen rearrangement upon exposure to N,O-bis(trimethylsilyl)acetamide-potassium acetate to yield the corresponding 2,3-disubstituted heteroaromatic products in good yield. However, for 1-(thien-2-yl)ethyl tosylacetates and substrates derived from 3-(hydroxyalkyl)indoles rearomatisation does not occur.

  呋喃-2-基甲基、噻吩-2-基甲基和吡咯-2-基甲基甲苯磺酸酯在暴露于 N,O-双(三甲基甲硅烷基)乙酰胺-乙酸钾后容易发生脱羧克莱森重排，从而产生相应的 2,3-二取代杂芳烃产物良好的产量。然而，对于甲苯磺酸 1-(噻吩-2-基)乙酯和衍生自 3-(羟烷基)吲哚的底物，不会发生再芳构化。
• Fe(III)‐Catalyzed, Cyclizative Coupling between 2‐Alkynylbenzoates and Carbinols: Rapid Generation of Polycyclic Isocoumarins and Phthalides and Mechanistic Study
  作者：Soniya Gandhi、Beeraiah Baire

  DOI：10.1002/adsc.202000313

  日期：2020.7.16

  catalyzed, highly regioselective cyclizative coupling of internal alkynes with alcohols has been reported for the rapid synthesis of structurally divergent, complex isocoumarins and phthalides respectively in intermolecular and intramolecular fashion. This strategy exhibited very high substrate scope and efficiency and proceeds through the simultaneous formation of C−O and C−C bonds. Observations from

  据报道，FeCl 3催化的内部炔烃与醇的高度区域选择性环化偶联可分别以分子间和分子内方式快速合成结构分歧，复杂的香豆素和邻苯二甲酸酯。该策略展示了很高的底物范围和效率，并且通过同时形成C-O和C-C键来进行。来自一系列对照实验的观察结果支持a）路易斯酸催化酯和醇的双重活化的机理，b）碳正离子化对提高环化速率的作用，即 例如，通过碳正离子活化炔烃，以及c）HCl在报道的级联过程中不起作用。
• Indium-Catalyzed Formal Carbon–Halogen Bond Insertion: Synthesis of α-Halo-α,α-disubstituted Esters from Benzylic Halides and Diazo Esters
  作者：Fei Wang、Yoshihiro Nishimoto、Makoto Yasuda

  DOI：10.1021/acs.orglett.2c00343

  日期：2022.3.4

  One-carbon-unit insertion into carbon–halogen (C–X) bonds accompanied by the formation of a new C–X bond and carbon–chain elongation is a powerful synthetic method of complex organohalides. Herein, we developed an indium trihalide catalyzed formal insertion of diazo esters into a C–X (X = Cl, Br, I) bond. In the present system, the reactions of α-aryl diazo esters with benzylic chlorides, bromides

  一个碳单元插入到碳-卤素（C-X）键中，伴随着新的C-X键的形成和碳-链的伸长，是复杂有机卤化物的一种强有力的合成方法。在此，我们开发了一种三卤化铟催化的重氮酯形式插入 C-X（X = Cl、Br、I）键。在本系统中，α-芳基重氮酯与苄基氯化物、溴化物和碘化物的反应分别生成 α-氯、α-溴和 α-碘酯。