4-methyl-N-(2-((trimethylsilyl)ethynyl)benzyl)benzenesulfonamide | 405198-84-7

• 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: 4-methyl-N-(2-((trimethylsilyl)ethynyl)benzyl)benzenesulfonamide
• 英文别名: 4-methyl-N-[[2-(2-trimethylsilylethynyl)phenyl]methyl]benzenesulfonamide
• CAS: 405198-84-7
• 化学式: C₁₉H₂₃NO₂SSi
• 分子量: 357.549
• InChiKey: PAHIEZSRBTVEJR-UHFFFAOYSA-N

物化性质

• 沸点：
  473.2±55.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(2-((trimethylsilyl)ethynyl)benzyl)benzenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 1-Methylene-2-(toluene-4-sulfonyl)-2,3-dihydro-1H-isoindole
  参考文献：
  名称：

  Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride

  摘要：

  The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents. on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00991-7
• 作为产物：
  描述：

  2-溴苯磺酰氯 在 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 10.0h， 生成 4-methyl-N-(2-((trimethylsilyl)ethynyl)benzyl)benzenesulfonamide
  参考文献：
  名称：

  钌催化杂环化形成吲哚，二氢异喹啉和二氢喹啉

  摘要：

  摘要 吲哚，二氢异喹啉和二氢喹啉是在胺/铵碱酸对存在下，通过钌催化的芳香族均-和双-高炔丙基胺/酰胺的杂环化反应而有效制备的。这些区域选择性5-内切和6-内型环化反应最可能是由键钌-偏二中间体的亲核捕集发生。 吲哚，二氢异喹啉和二氢喹啉是在胺/铵碱酸对存在下，通过钌催化的芳香族均-和双-高炔丙基胺/酰胺的杂环化反应而有效制备的。这些区域选择性5-内切和6-内型环化反应最可能是由键钌-偏二中间体的亲核捕集发生。

  DOI：

  10.1055/s-0032-1316539

文献信息

• Ruthenium-Catalyzed Cycloisomerization of Aromatic Homo- and Bis-Homopropargylic Amines/Amides: Formation of Indoles, Dihydroisoquinolines and Dihydroquinolines
  作者：Alejandro Varela-Fernández、Jesús A. Varela、Carlos Saá

  DOI：10.1002/adsc.201100095

  日期：2011.8

  Ruthenium-catalyzed cycloisomerizations of aromatic homo- and bis-homopropargylic amines/amides efficiently afford indoles, dihydroisoquinolines and dihydroquinolines. These processes were regioselective (5- and 6-endo cyclizations) on using key Ru vinylidene intermediates. The presence of an amine/ammonium base-acid pair increased the rate of cyclization and facilitated the catalytic turnover.

  钌催化的芳族均和双均炔丙基胺/酰胺的环异构化可有效提供吲哚，二氢异喹啉和二氢喹啉。这些方法是区域选择性（5-和6-内使用键茹偏中间体的环化反应）。胺/铵基酸对的存在增加了环化速率并促进了催化转化。
• Palladium‐Catalyzed Synthesis of 6 <i>H</i> ‐Dibenzo[ <i>c,h</i> ]chromenes and 5,6‐Dihydrobenzo[ <i>c</i> ]phenanthridines: Application to the Synthesis of Dibenzo[ <i>c,h</i> ]chromene‐6‐ones, Benzo[ <i>c</i> ]phenanthridines, and <i>Arnottin I</i>
  作者：Subhendu Pramanik、Moumita Jash、Debasmita Mondal、Chinmay Chowdhury

  DOI：10.1002/adsc.201900833

  日期：2019.11.19

  6H‐Dibenzo[c,h]chromenes and 5,6‐dihydrobenzo[c]phenanthridines have been synthesized via Palladium (II)‐catalyzed domino reactions of acetylenic substrates involving intramolecular trans‐oxo/amino palladation onto the triple bond followed by nucleophilic addition of the intermediate to a tethered cyano/aldehyde. The scope of this reaction was extended through one step conversion of some of the products

  通过钯（II）催化的炔属底物的多米诺骨反应，合成了6 H-二苯并[ c，h ]色环和5,6-二氢苯并[ c ]菲啶，涉及分子内反式-羰基/氨基palpalation到三键，然后是亲核的将中间体加到束缚的氰基/醛中。通过将一些产物一步转化为6 H-二苯并[ c，h ]铬-6-6和苯并[ c ]菲啶扩大了反应的范围。这种方法的使用导致了天然产物Arnottin I的正式全合成。
• Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions
  作者：Laura Antonella Aronica、Gianluigi Albano、Luca Giannotti、Elisa Meucci

  DOI：10.1002/ejoc.201601392

  日期：2017.2.3

  A one‐step synthesis of functionalised isoindolines and dihydrobenzoazepines was developed through copper‐free, palladium‐catalysed cyclocarbonylative Sonogashira reactions between tosylamides and iodoarenes.

  通过甲苯磺酰胺和碘代芳烃之间无铜，钯催化的环羰基Sonogashira反应，一步一步合成了官能化的二氢吲哚啉和二氢苯并氮杂s。
• Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies
  作者：Qing Zhao、David Fabian León Rayo、Dominic Campeau、Martin Daenen、Fabien Gagosz

  DOI：10.1002/anie.201807136

  日期：2018.10.8

  synthesis of a variety of N‐containing aromatic heterocycles by a formal gold‐catalyzed dehydro‐Diels–Alder reaction of ynamide derivatives has been developed. Deuterium‐labeling experiments and kinetic studies support the involvement of a dual gold catalysis mechanism in which a gold acetylide moiety adds onto an aurated keteneiminium.

  通过正式的金催化的乙酰胺衍生物的脱氢-狄尔斯-阿尔德反应，已开发出一种用于合成多种含氮芳族杂环的新方案。氘标记实验和动力学研究支持双重金催化机制的参与，在该机制中，乙炔酸金部分加入了经过酸化的烯酮亚胺。
• Synthesis of Spiroaminals and Spiroketals with Bimetallic Relay Catalysis
  作者：Xianghua Wang、Shuli Dong、Zhili Yao、Lei Feng、Philias Daka、Hong Wang、Zhenghu Xu

  DOI：10.1021/ol4033286

  日期：2014.1.3

  A novel tandem metal relay catalytic system was developed by combining gold-catalyzed cycloisomerization with an early transition-metal-catalyzed inverse-electron-demand hetero-Diels-Alder (IED-HDA) reaction. Various biologically important spiroaminals and spiroketals were obtained with very high efficiency under mild conditions.