4-methyl-N-((4-nitrophenyl)(phenyl)methyl)benzenesulfonamide

• 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-((4-nitrophenyl)(phenyl)methyl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(4-nitrophenyl)-phenylmethyl]benzenesulfonamide
• 化学式: C₂₀H₁₈N₂O₄S
• 分子量: 382.44
• InChiKey: CNIQHIPCZOMBMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲苯磺酰胺 在 2,2'-联吡啶 、 三氟化硼乙醚 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 生成 4-methyl-N-((4-nitrophenyl)(phenyl)methyl)benzenesulfonamide
  参考文献：
  名称：

  用于催化醛亚胺与有机硼试剂不对称芳基化的含手性二膦和 NHC 的钌催化剂

  摘要：

  我们首次报道了 [RuCl2(η6-p-cymene)]2 在 N-活化醛亚胺与硼酸及其衍生物的芳基化反应中的应用，以得到手性胺，这是合成关键生物活性物质的重要中间体。化合物。研究了手性配体、亚胺底物和有机硼试剂的行为。获得了非常好的对映选择性。

  DOI：

  10.1002/ejoc.201200556

文献信息

• 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。
• In situ generated cationic Pd(II)/bipyridine-catalyzed addition of arylboronic acids to N -sulfonyl-arylaldimines
  作者：Zhenyu Yang、Yuxin Ni、Rui Liu、Kaixuan Song、Shaohui Lin、Qinmin Pan

  DOI：10.1016/j.tetlet.2017.04.035

  日期：2017.5

  An in situ generated cationic Pd(II)/bipyridine-catalyzed nucleophilic addition of arylboronic acids to N-sulfonyl arylaldimines was developed and optimized, and the reaction was proceeded highly efficiently and conveniently in CH3NO2. A series of arylboronic acids and N-sulfonyl arylaldimines were surveyed, and 12 of 13 examples gave 90∼96% yields.

  开发并优化了原位生成的阳离子Pd（II）/联吡啶催化的芳基硼酸向N-磺酰基芳基亚胺的亲核加成反应，并在CH 3 NO 2中高效且方便地进行了反应。考察了一系列芳基硼酸和N-磺酰基芳基亚胺，在13个实施例中的12个给出了90〜96％的收率。
• Aluminum Triflate as a Powerful Catalyst for Direct Amination of Alcohols, Including Electron‐Withdrawing Group‐Substituted Benzhydrols
  作者：Takashi Ohshima、Junji Ipposhi、Yasuhito Nakahara、Ryozo Shibuya、Kazushi Mashima

  DOI：10.1002/adsc.201200536

  日期：2012.9.17

  Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron‐withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo‐substituted product was further transformed into letrozole.

  三氟甲磺酸铝[Al（OTf）3 ]有效催化具有吸电子（F，Br，I，NO 2或CN）取代基的烯丙醇，苄醇和苯羟基的直接胺化，从而以高收率提供相应的联芳基胺，然后将二溴取代的产物进一步转化为来曲唑。
• 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）。
• Rhodium catalyzed three-component reaction of aldehyde, boronic acid, and sulfonamides: a facile one-pot synthesis of diarylmethylamines
  作者：Ponnam Satyanarayana、Ganapam Manohar Reddy、Hariharasarma Maheswaran、Mannepalli Lakshmi Kantam

  DOI：10.1016/j.tetlet.2014.08.003

  日期：2014.10

  Rhodium(I) catalyzed three-component reaction for the one pot synthesis of diarylmethylamines in excellent yields were achieved by using aldehyde, boronic acid, and sulfonamides. The use of hyper-valent bis(trifluoroacetoxy)iodobenzene as an additive plays a key role in the chemo selective formation of amines instead of alcohols.

  使用醛，硼酸和磺酰胺可实现铑（I）催化三组分反应，从而一锅合成二芳基甲胺，且收率很高。使用高价的双（三氟乙酰氧基）碘苯作为添加剂在胺而不是醇的化学选择性形成中起关键作用。