N-phenyl-N-[(4-tolylsulfonyl)methyl](2-furyl)amine | 158471-23-9

• 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-phenyl-N-[(4-tolylsulfonyl)methyl](2-furyl)amine
• 英文别名: N-(furan-2-yl(phenyl)methyl)-4-methylbenzenesulfonamide；N-[(2-furyl)phenylmethyl]-4-methylbenzenesulfonamide；N-[furan-2-yl(phenyl)methyl]-4-methylbenzenesulfonamide
• CAS: 158471-23-9
• 化学式: C₁₈H₁₇NO₃S
• 分子量: 327.404
• InChiKey: DDWQDUCHSJIPET-UHFFFAOYSA-N

物化性质

• 沸点：
  468.3±55.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phenyl-N-[(4-tolylsulfonyl)methyl](2-furyl)amine 在 jones reagent 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 0.25h， 生成 6-phenyl-1-(4-tolylsulfonyl)-1,6-dihydropyridine-2,5-dione
  参考文献：
  名称：

  1,4-Reductive Addition of Hydrazoic Acid to γ-Oxo-α,β-unsaturated δ-Lactones and -Lactams: A Convenient Route to α-Amino-γ-oxo-α,β-unsaturated δ-Lactones and -Lactams

  摘要：

  gamma-Oxo-alpha,beta-unsaturated delta-lactones and lactams, which are easily accessible from their corresponding 2-furylcarbinols, were used as substrates for the 1,4-reductive addition of hydrazoic acid. The outcome of the reaction is the formation, in high yields, of the corresponding alpha-amino-gamma-oxo-alpha,beta-unsaturated delta-lactones and -lactams, compounds of great biological and synthetic interest.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1449::aid-ejoc1449>3.0.co;2-9
• 作为产物：
  描述：

  2-呋喃基(苯基)甲醇 在 palladium on activated charcoal 迭氮酸 、 硫酸 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 4.67h， 生成 N-phenyl-N-[(4-tolylsulfonyl)methyl](2-furyl)amine
  参考文献：
  名称：

  1,4-Reductive Addition of Hydrazoic Acid to γ-Oxo-α,β-unsaturated δ-Lactones and -Lactams: A Convenient Route to α-Amino-γ-oxo-α,β-unsaturated δ-Lactones and -Lactams

  摘要：

  gamma-Oxo-alpha,beta-unsaturated delta-lactones and lactams, which are easily accessible from their corresponding 2-furylcarbinols, were used as substrates for the 1,4-reductive addition of hydrazoic acid. The outcome of the reaction is the formation, in high yields, of the corresponding alpha-amino-gamma-oxo-alpha,beta-unsaturated delta-lactones and -lactams, compounds of great biological and synthetic interest.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1449::aid-ejoc1449>3.0.co;2-9

文献信息

• Iridium-Catalyzed Highly Regioselective and Diastereoselective Allylic Etherification To Access <i>cis</i>-2,6-Disubstituted Dihydropyridinones
  作者：Wangze Song、Ming Li、Nan Zheng、Karim Ullah、Junhao Li、Kun Dong、Yubin Zheng

  DOI：10.1021/acs.joc.8b01598

  日期：2018.10.19

  A highly regio- and diastereoselective method to access cis-2,6-disubstituted dihydropyridinones under mild conditions by an iridium-catalyzed allylic etherification is reported. cis-2,6-Disubstituted dihydropyridinones are important precursors for the de novo synthesis of the corresponding piperidine alkaloids and iminosugars. This strategy features a broad substrate scope, high yields, and excellent

  报道了一种高度区域选择性和非对映选择性的方法，该方法通过铱催化的烯丙基醚化反应在温和条件下获得顺式-2,6-二取代的二氢吡啶并酮。顺式-2，6-二取代的二氢吡啶并酮是从头合成相应的哌啶生物碱和亚氨基糖的重要前体。该策略具有广泛的底物范围，高收率以及出色的区域选择性和非对映选择性。该机理涉及π-烯丙基-Ir中间体。来自甲苯磺酰基的强A 1,3-菌株也可能在这种转化中有利于顺式产物的形成。
• Tertiary Amine-Triggered Cascade S_N2/Cycloaddition: An Efficient Construction of Complex Azaheterocycles under Mild Conditions
  作者：Jian Hu、Bing Tian、Xinyan Wu、Xiaofeng Tong

  DOI：10.1021/ol302329b

  日期：2012.10.5

  In this paper, an amine-triggered cascade SN2/cycloaddtion sequence between 2-(acetoxymethyl)buta-2,3-dienoate 1 and various π-system functionalized tosylamides 3 has been reported, which provides a facile method for stereoselective construction of structurally diverse azaheterocycles.

  在本文中，已经报道了在2-（乙酰氧基甲基）丁2,3-二烯酸酯1和各种π-系统官能化的甲苯磺酰胺3之间的胺触发级联S N 2 /环加成序列，为立体选择性构建Sn 2提供了一种简便的方法。结构上不同的氮杂杂环。
• Palladium-Catalyzed Addition of Arylboronic Acids to <i>N</i>-Tosylarylimines
  作者：Huayue Wu、Jiang Cheng、Qiang Zhang、Jiuxi Chen、Miaochang Liu、Changming Qin、Weike Su、Jinchang Ding

  DOI：10.1055/s-2008-1042932

  日期：2008.4

  Pd-catalyzed addition of arylboronic acids to N-tosyl­arylimines was described by employing easily prepared, air-stable aminophosphine ligands, cheap inorganic base, and common organic solvents, providing diarylmethylamine derivatives through one-pot synthesis in moderate to good yields. The efficiency of this reaction was demonstrated by the compatibility with nitro, trifluoro­methyl, fluoro, chloro, and methoxy groups. Moreover, rigorous exclusion of air/moisture is not required in these transformations.

  通过使用易于制备、空气稳定且价格低廉的氨基膦配体、廉价的碱和常见的溶剂，钯催化的芳基硼酸与N-甲磺酰芳基亚胺的加成反应，可在温和至良好产率下通过一锅法合成二芳基甲基胺衍生物。该反应的高效性体现在其对硝基、三氟甲基、氟、氯和甲氧基等官能团的兼容性。此外，这些转化过程并不严格要求无空气/水分的环境。
• Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles
  作者：Tomohiro Yasukawa、Tatsuya Kuremoto、Hiroyuki Miyamura、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.6b01172

  日期：2016.6.3

  Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported

  已开发了异质手性铑纳米粒子催化的亚胺的不对称芳基化反应。该反应在水性介质中进行，没有亚胺通过水解显着分解，以高收率提供手性（二芳基甲基）胺，具有出色的对映选择性。在迄今为止报道的用于这些反应的非均相催化剂中，该催化剂体系表现出最高的转换数（700）。还证明了催化剂的可重复使用性。
• Rhodium-catalyzed and sonication-accelerated addition of aryltin and aryllead reagents to imines in air and water
  作者：Rui Ding、Cui Huo Zhao、Yong Jun Chen、Li Liu、Dong Wang、Chao Jun Li

  DOI：10.1016/j.tetlet.2004.01.160

  日期：2004.3

  In the presence of a rhodium catalyst, imines (1a–k) react with phenyltrimethyltin 2a or phenyltrimethyllead 2b in water and air under ultrasonic irradiation at 35 °C to give the corresponding diarylmethylamines (3a–k) in good yields.

  在铑催化剂的存在下，亚胺（1a – k）与苯三甲基锡2a或苯基三甲基铅2b在35°C的超声辐射下在水和空气中反应，以高收率得到相应的二芳基甲胺（3a – k）。