N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide | 65690-69-9

• 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-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide
• 英文别名: N-[1,1'-Biphenyl]-4-yl-4-methylbenzenesulfonamide；4-methyl-N-(4-phenylphenyl)benzenesulfonamide
• CAS: 65690-69-9
• 化学式: C₁₉H₁₇NO₂S
• 分子量: 323.415
• InChiKey: VOJVNWBUZFVCEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  492.8±48.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide 在 硝酸 、 溶剂黄146 作用下， 生成 N-(3,5-dinitro-biphenyl-4-yl)-N-methyl-toluene-4-sulfonamide
  参考文献：
  名称：

  Bell, Journal of the Chemical Society, 1928, p. 2778

  摘要：

  DOI：
• 作为产物：
  描述：

  N-羟基-4-氨基联苯 在 吡啶 作用下， 生成 N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Bell; Kenyon; Robinson, Journal of the Chemical Society, 1926, p. 1244

  摘要：

  DOI：

文献信息

• A highly efficient heterogeneous copper-catalyzed Chan–Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides
  作者：Chongren You、Fang Yao、Tao Yan、Mingzhong Cai

  DOI：10.1039/c6ra04298h

  日期：——

  A heterogeneous Chan–Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an L-proline-functionalized MCM-41-immobilized copper(I) complex [MCM-41–L-proline–CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily

  在室温下，在存在10 mol％的L-脯氨酸官能化的MCM-41固定化铜（I）络合物[MCM-41– L]的情况下，在MeOH中实现了磺酰叠氮化物与芳基硼酸之间的异质Chan-Lam偶联反应-脯氨酸–CuCl ]在空气中产生多种N-芳基磺酰胺，收率极高。新的多相铜络合物可以由市售的廉价试剂制备，并通过简单过滤反应溶液进行回收，并循环至少8次而不会降低活性。
• Synthesis of <i>N</i>-arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates
  作者：Bo Yang、Chang Lian、Guanglu Yue、Danyang Liu、Liyan Wei、Yi Ding、Xiancai Zheng、Kui Lu、Di Qiu、Xia Zhao

  DOI：10.1039/c8ob02226g

  日期：——

  A novel one-step direct reductive coupling reaction between nitroarenes and sodium arylsulfinates was realized in the presence of an inexpensive Pd/C catalyst. In this procedure, readily available nitroarenes are employed as the nitrogen sources, and sodium arylsulfinates serve as both coupling partners and reductants. The method features high efficiency by using cheap Pd/C with low catalyst loading

  在廉价的Pd / C催化剂的存在下，实现了硝基芳烃与芳基亚磺酸钠之间新颖的一步式直接还原偶联反应。在该方法中，将易得的硝基芳烃用作氮源，而芳基次磺酸钠既用作偶联配偶体又用作还原剂。该方法的特点是在不添加任何其他还原剂或配体的情况下，通过使用廉价的Pd / C，低催化剂负载量和良好的官能团耐受性来实现高效率。这种简便而温和的合成方法能够从容易获得的底物中高效合成官能化的N-芳基磺酰胺。
• Direct CH Amidation of Benzoic Acids to Introduce<i>meta</i>- and<i>para</i>-Amino Groups by Tandem Decarboxylation
  作者：Donggun Lee、Sukbok Chang

  DOI：10.1002/chem.201500331

  日期：2015.3.27

  The Ir‐catalyzed mild CH amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional‐group compatibility. Subsequent protodecarboxylation of ortho‐amidated benzoic acid products afforded meta‐ or para‐substituted (N‐sulfonyl)aniline derivatives, the latter being inaccessible by other CH functionalization approaches. The decarboxylation step

  开发了具有磺酰叠氮化物的苯甲酸的Ir催化轻度CH酰胺化反应，可实现高效且具有官能团相容性的反应。随后，将氨基酰胺化的邻氨基苯甲酸产物进行原羧化反应，可得到间位或对位取代的（N-磺酰基）苯胺衍生物，而其他CH官能化方法则无法获得后者。脱羧步骤与酰胺化条件兼容，可实现方便的一锅两步工艺。
• Accessing bridged bicyclic compounds or meta carbon-functionalized anilines from the dearomatization of anilines
  作者：Linfei Wang、Shuo-En Wang、Weibin Wang、Renhua Fan

  DOI：10.1039/c3ra23224g

  日期：——

  The oxidative dearomatization of anilines was combined with a domino Michael addition, providing a series of nitrogen-containing bridged bicyclic compounds in moderate to excellent yields. The bridged bicyclic compound could be converted into the corresponding meta carbon-functionalized aniline derivative via a quinine-catalyzed tandem retro-oxa-Michael addition–aromatization reaction.

  将苯胺的氧化脱芳构化与多米诺Michael加成反应相结合，可以中等至优异的产率获得一系列含氮的桥联双环化合物。这些桥联双环化合物可通过喹啉催化的串联逆氧迈克尔加成-芳构化反应转化为相应的间位碳功能化苯胺衍生物。
• Selective C3C3 Oxidative Cross-Coupling between Unactivated Anilines and Indoles
  作者：Linfei Wang、Zhaomeng Han、Renhua Fan

  DOI：10.1002/adsc.201000603

  日期：2010.12.17

  A selective C3C3 oxidative cross-coupling between unactivated anilines and indoles catalyzed by copper bromide together with iodobenzene diacetate as the oxidant is described. This methodology provides a novel approach to biaryl synthesis.

  描述了溴化铜与碘代苯二乙酸酯作为氧化剂催化的未活化苯胺和吲哚之间的选择性C3C3氧化交叉偶联。这种方法为联芳基的合成提供了一种新颖的方法。

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