N-(4-甲基亚苄基)-4-甲基苯磺酰胺 | 75159-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-甲基亚苄基)-4-甲基苯磺酰胺
• 英文名称: N-(4-methylbenzylidene)-p-toluenesulfonamide
• 英文别名: 4-methyl-N-(4-methylbenzylidene)benzenesulfonamide；N-(4-methylbenzylidene)-4-methylbenzenesulfonamide；4-methyl-N-[(4-methylphenyl)methylene]benzenesulfonamide；4-methyl-N-[(4-methylphenyl)methylidene]benzenesulfonamide
• CAS: 75159-10-3
• 化学式: C₁₅H₁₅NO₂S
• 分子量: 273.356
• InChiKey: CEZQVKAFKQRFDG-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  425.1±48.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-甲基亚苄基)-4-甲基苯磺酰胺 在 [Ir(COD)(SnCl3)Cl(μ-Cl)]2 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 5,5'-(p-tolylmethylene)bis(2-methylthiophene)
  参考文献：
  名称：

  Heterobimetallic Ir–Sn catalysis: aza-Friedel–Crafts reaction of N-sulfonyl aldimines

  摘要：

  The heterobimetallic complex [Ir(COD)(SnCl3)Cl(mu-Cl)](2) catalyzes the aza-Friedel Crafts reaction of 1,3,5-trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp(3) C-N bond and elimination of 1,3,5-trimethoxybenzene. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.074
• 作为产物：
  描述：

  N-(1-p-tolylbut-3-enyl)-4-methylbenzenesulfonamide 在 碘苯二乙酸 、 碘 、 sodium acetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以61%的产率得到N-(4-甲基亚苄基)-4-甲基苯磺酰胺
  参考文献：
  名称：

  Base-promoted selective β-fragmentation of homoallylamines

  摘要：

  A selective beta-fragmentation of homoallylamines with the combination of iodobenzene diacetate, iodine, and sodium acetate is reported. The desired carbon-carbon bond cleavage proceeded via a radical beta-scission pathway under mild conditions with good functional group tolerance. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.031

文献信息

• Nickel(0)-Catalyzed [2 + 2 + 1] Carbonylative Cycloaddition of Imines and Alkynes or Norbornene Leading to γ-Lactams
  作者：Yoichi Hoshimoto、Tomoya Ohata、Yukari Sasaoka、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1021/ja509171a

  日期：2014.11.12

  The first nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition reaction of imines and alkynes or norbornene has been achieved by employing phenyl formate as a CO source. With this method, a variety of N-benzenesulfonyl, -tosyl, and -phosphoryl-substituted γ-lactams can be prepared in good to high yields.

  通过使用甲酸苯酯作为 CO 源，实现了第一个镍（0）催化的亚胺和炔烃或降冰片烯的 [2 + 2 + 1] 羰基化环加成反应。使用这种方法，可以高产率地制备各种 N-苯磺酰基、-甲苯磺酰基和-磷酰基取代的 γ-内酰胺。
• Palladium-Catalyzed Benzylic Addition of 2-Methyl Azaarenes to <i>N</i>-Sulfonyl Aldimines via C−H Bond Activation
  作者：Bo Qian、Shengmei Guo、Jianping Shao、Qiming Zhu、Lei Yang、Chungu Xia、Hanmin Huang

  DOI：10.1021/ja910104n

  日期：2010.3.24

  generation of amines by palladium-catalyzed nucleophilic benzylic addition of 2-methyl-substituted azaarenes to N-sulfonyl aldimines under neutral conditions via C-H bond activation has been developed. This reaction represents a very efficient methodology for the synthesis of heterocycle-containing amines and thus opens a new way to access amines through C-H bond activation.

  已开发出一种通过在中性条件下通过 CH 键活化将 2-甲基取代的氮杂芳烃与 N-磺酰基醛亚胺进行钯催化的亲核苄基加成生成胺的有效方案。该反应代表了一种非常有效的合成含杂环胺的方法，因此开辟了一种通过 CH 键活化获得胺的新方法。
• Iron-Catalyzed Direct Alkenylation of 2-Substituted Azaarenes with <i>N</i>-Sulfonyl Aldimines via C–H Bond Activation
  作者：Bo Qian、Pan Xie、Yinjun Xie、Hanmin Huang

  DOI：10.1021/ol200684b

  日期：2011.5.20

  A novel iron-catalyzed alkenylation of 2-substituted azaarenes through sp3 C–H bond activation has been developed. A favorable E2-elimination is proposed as a key step to cleavage of C–H and C–N bonds for the construction of a C═C bond in high stereoselectivity. This transformation represents an efficient way to synthesize 2-alkenylated azaarenes from simple starting materials.

  通过sp 3 C–H键活化，已开发出一种新型的铁催化的2-取代的氮杂芳烃的烯基化反应。提出了一种有利的消除E2的方法，作为裂解C–H和C–N键的关键步骤，以高立体选择性构建C═C键。这种转化代表了一种由简单的起始原料合成2-烯基化氮杂芳烃的有效方法。
• Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene
  作者：Xun Lu、Uwe Schneider

  DOI：10.1039/c6cc06201f

  日期：——

  Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles.

  使用双（二烷基）cyclopropenylidene（BAC）催化已经研制成功，它依赖于一个正式的极性转换迈克尔受体亲核试剂的活化。
• α-Aryl-Substituted Allenamides in an Imino-Nazarov Cyclization Cascade Catalyzed by Au(I)
  作者：Zhi-Xiong Ma、Shuzhong He、Wangze Song、Richard P. Hsung

  DOI：10.1021/ol302743k

  日期：2012.11.16

  An imino-Nazarov cyclization using α-aryl-substituted allenamides is described. This gold(I)-catalyzed cascade is efficient and regioselective in constructing a diverse array of synthetically useful aromatic-ring fused cyclopentenamides. The success in this transformation represents a solution to the challenge in establishing an imino-Nazarov cyclization process.

  描述了使用 α-芳基取代的丙二烯酰胺的亚氨基-纳扎罗夫环化。这种金（I）催化的级联在构建各种合成有用的芳环稠合环戊烯酰胺方面是有效的和区域选择性的。这种转化的成功代表了对建立亚氨基-纳扎罗夫环化过程挑战的解决方案。