N-(4-Ethylbenzylidene)-4-methylbenzenesulfonamide | 951762-59-7

• 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-(4-Ethylbenzylidene)-4-methylbenzenesulfonamide
• 英文别名: (NE)-N-[(4-ethylphenyl)methylidene]-4-methylbenzenesulfonamide
• CAS: 951762-59-7
• 化学式: C₁₆H₁₇NO₂S
• 分子量: 287.382
• InChiKey: AICXXMQFQOQWPE-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  丙烯醛 、 N-(4-Ethylbenzylidene)-4-methylbenzenesulfonamide 在 JandaJel-(OMe)-PPh₃ resin 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到N-[2-formyl-1-(4-ethylphenyl)allyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  用于aza-Morita-Baylis-Hillman反应的聚苯乙烯负载的三苯基膦催化剂的优化

  摘要：

  研究了一系列极性基团官能化的聚苯乙烯负载的膦试剂作为N-甲苯磺酰基芳氨酸的aza-Morita-Baylis-Hillman反应和各种Michael受体的催化剂，目的是确定最佳的聚合物/溶剂组合。对于这些反应，在THF溶剂中，聚苯乙烯主链上含有甲氧基（JJ -OMe-PPh 3）的J anda J el-PPh 3（1 mmol PPh 3 / g载量）提供了最高的收率。 。将甲基醚基团结合到JJ -OMe-PPh 3中 使用市售的4-甲氧基苯乙烯，因此这种极性聚苯乙烯树脂是容易获得的，并且应该用作亲核催化剂载体。

  DOI：

  10.1016/j.tet.2005.05.108
• 作为产物：
  描述：

  对甲苯磺酰胺 、 4-乙基苯甲醛 在 三氟化硼乙醚 作用下， 生成 N-(4-Ethylbenzylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I

  摘要：

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.

  DOI：

  10.1021/ja070274n

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。
• Novel Base-Catalyzed Olefination Methodology. Stereoselective Synthesis of (E)-α-Benzenesulfinylvinylphosphonates
  作者：Yanchang Shen、Guo-Fang Jiang

  DOI：10.1055/s-2000-6221

  日期：——

  A novel olefination, catalyzed by base(NaH) and its application to the stereoselective synthesis of substituted (E)-α-benzenesulfinyl vinylphosphonates are described.

  描述了一种由碱 (NaH) 催化的新型烯化反应及其在立体选择性合成取代 (E)-α-苯亚磺酰基乙烯基膦酸酯中的应用。
• Cobalt-catalyzed reductive Mannich reactions of 4-acryloylmorpholine with N-tosyl aldimines
  作者：Oscar Prieto、Hon Wai Lam

  DOI：10.1039/b715839d

  日期：——

  Using cobalt catalysis, diethylzinc promotes the conjugate reduction of 4-acryloylmorpholine to produce the corresponding ethylzinc enolate, which reacts with N-tosyl aldimines to afford β-aminoamides.

  利用钴催化，二乙基锌促进 4-丙烯酰吗啉的共轭还原，生成相应的乙基锌烯醇化物，其与 N-甲苯磺酰醛亚胺反应生成 β-氨基酰胺。
• Small molecules for endothelial cell activation
  申请人：Cruz Daniel

  公开号：US10197557B2

  公开（公告）日：2019-02-05

  The present invention provides small molecules for endothelial cell activation and compositions thereof and methods of making and using the same.

  本发明提供了用于内皮细胞活化的小分子及其组合物以及制造和使用方法。
• Highly Efficient aza-Baylis−Hillman Reaction of <i>N</i>-Tosylated Imines with MVK, Acrolein, and Phenyl Acrylate or α-Naphthyl Acrylate:  Lewis Base Effects and A Convenient Method to Synthesize α,β-Unsaturated β-Amino Carbonyl Compounds
  作者：Yong-Mei Xu、Min Shi

  DOI：10.1021/jo035103p

  日期：2004.1.1

  This paper describes several highly efficient aza-Baylis-Hillman reactions of N-tosylated imines with MVK, acrolein, and phenyl acrylate or alpha-naphthyl acrylate in the presence of a Lewis base. In most cases, the reaction can be completed within 1 h using the appropriate Lewis base catalyst. An efficient method to synthesize beta-amino ketones, aldehydes and esters in high yields and short reaction time has been developed.