N-((2-methoxyphenyl)ethynyl)-N,4-dimethylbenzenesulfonamide | 1535484-70-8

• 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: N-((2-methoxyphenyl)ethynyl)-N,4-dimethylbenzenesulfonamide
• 英文别名: N-[2-(2-methoxyphenyl)ethynyl]-N,4-dimethylbenzenesulfonamide
• CAS: 1535484-70-8
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: VOQHIROSIUVNQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-((2-methoxyphenyl)ethynyl)-N,4-dimethylbenzenesulfonamide 在 bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到N-(3-iodobenzofuran-2-yl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Iodocyclization of Ethoxyethyl Ethers to Ynamides: An Immediate Construction to Benzo[b]furans

  摘要：

  The iodocyclization of ethoxyethyl ethers to ynamides was completed within three seconds. The corresponding benzo[b]furans were obtained in high yields (84%-quant.) under mild conditions.

  DOI：

  10.1021/jo500903y
• 作为产物：
  描述：

  2-乙炔基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 N-((2-methoxyphenyl)ethynyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  金催化2-乙炔基苯胺与酰胺的环状[4 + 2]环化：获得取代的2-氨基喹啉的途径

  摘要：

  易于催化的2-乙炔基苯胺与金酰胺的金催化分子间[4 + 2]环化为合成取代的2-氨基喹啉提供了高度区域选择性，模块化，高效且原子经济的策略，产率高达93％。

  DOI：

  10.1002/adsc.201800341

文献信息

• Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and Iodo-Imidation of Ynamides
  作者：Rajendra K. Mallick、B. Prabagar、Akhila K. Sahoo

  DOI：10.1021/acs.joc.7b02124

  日期：2017.10.6

  A novel and straightforward protocol is demonstrated for the synthesis of highly substituted oxazoles from readily accessible ynamides in the presence of ytterbium(III) trifluoromethanesulfonate [Yb(OTf)3], N-iodosuccinimide (NIS), and acetonitrile. Multiple oxazole skeletons in the aryl periphery are constructed in a single operation for the first time. The hydroamidation and iodo-imidation of ynamides

  一种新颖而直接的方案已证明，可以在三氟甲磺酸（（Yb（OTf）3 ]，N-碘代琥珀酰亚胺（NIS）和乙腈存在下，由易于获得的酰胺酰胺合成高度取代的恶唑。首次在单个操作中构建了芳基外围的多个恶唑骨架。举例说明了将酰胺酰胺加氢酰胺化和碘酰亚胺化成三取代和四取代的烯酮缩醛。同位素标记实验用于识别此转化中的氧源。反应可扩展至克级，证明了转换的鲁棒性。
• Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl‐Gold Promoted Intermolecular Ynamide Addition to Aldehydes
  作者：Teng Yuan、Kelton Radefeld、Chuan Shan、Carter Wegner、Erin Nichols、Xiaohan Ye、Qi Tang、Lukasz Wojtas、Xiaodong Shi

  DOI：10.1002/anie.202305810

  日期：2023.8

  application of Fe(acac)3 as a cocatalyst prevents vinyl gold protodeauration, allowing for its nucleophilic addition to aldehydes. Hence, the intermolecular vinyl gold-promoted asymmetric hydrative aldol reaction (HAR) of ynamides and aldehydes was shown possible and is herein presented. The reaction leads to β-hydroxy amides with high yields (up to 95 %) and stereoselectivity (up to >20 : 1 d.r, 99 % ee) under

  Fe(acac) 3作为助催化剂的应用可防止乙烯基金原脱气，从而使其能够与醛发生亲核加成。因此，分子间乙烯基金促进的炔酰胺和醛的不对称水合羟醛反应（HAR）被证明是可能的，并在本文中提出。该反应在温和条件（无碱，40 °C）下产生高产率（高达 95 %）和立体选择性（高达 >20 : 1 dr，99 % ee）的 β-羟基酰胺。
• Microwave-Assisted Copper-Catalyzed Coupling of Bromoalkynes and Sulfonamides: Rapid Synthesis of N-Sulfonyl Ynamides
  作者：Joon-Ho Lee、Hyun-Suk Yeom、Su Jeong Hong

  DOI：10.1055/a-2196-8886

  日期：——

  The synergistic effect of an alcohol solvent and microwave irradiation dramatically increased the C–N coupling rate, enabling the rapid synthesis of N-sulfonyl ynamides in ten minutes. The optimal catalyst, ligand, and solvent combination was investigated, and various bromoalkynes and sulfonamides were shown to be tolerated under these conditions.

  醇溶剂和微波辐射的协同作用显着提高了C-N偶联速率，使得N-磺酰基炔酰胺能够在10分钟内快速合成。研究了最佳的催化剂、配体和溶剂组合，并且显示在这些条件下可以耐受各种溴代炔烃和磺酰胺。
• Copper-catalyzed room-temperature cross-dehydrogenative coupling of secondary amides with terminal alkynes: a chemoselective synthesis of ynamides
  作者：Shuang-Yan Zhuo、Jian-Liang Ye、Xiao Zheng

  DOI：10.1039/d3ob02032k

  日期：——

  A copper-catalyzed aerobic oxidative cross-dehydrogenative coupling reaction between secondary amides and terminal alkynes has been developed. With the aid of ligands and 3 Å molecular sieves, ynamides can be efficiently synthesized at room temperature and conveniently scaled up. A legitimate mechanism involving nitrogen-centred radicals and copper trivalent intermediates has been proposed.

  已经开发出仲酰胺和末端炔之间的铜催化的有氧氧化交叉脱氢偶联反应。借助配体和 3 Å 分子筛，可以在室温下高效合成 ynamides，并方便地放大生产。已经提出了涉及以氮为中心的自由基和三价铜中间体的合法机制。
• Step‐Economical Route to 2‐Amido‐3‐bromobenzo[ <i>b</i> ]thiophenes <i>via</i> Ynamide Formation and Selectfluor‐Mediated Oxidative Bromocyclization
  作者：Su Jeong Hong、Chang Ju Yoon、Hee Nam Lim、Hyun‐Suk Yeom

  DOI：10.1002/ejoc.202101093

  日期：2021.11.8

  AbstractA one‐pot synthesis of 2‐amido‐3‐bromobenzo[b]thiophenes based on C−N coupling and oxidative bromocyclization reactions was developed. This enables a modular approach to obtain diverse substituents at the C2 position of benzothiophenes by employing structurally modified sulfonamides. Oxidative cyclization was driven by Selectfluor and represents a previously unreported recycling method for the bromide anion byproducts of the C−N bond coupling step. The details of the study are described fully herein.