4-methyl-N'-(1-(2,4,6-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide | 1416164-16-3

• 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'-(1-(2,4,6-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide
• 英文别名: 4-methyl-N-[1-(2,4,6-trimethoxyphenyl)ethylideneamino]benzenesulfonamide
• CAS: 1416164-16-3
• 化学式: C₁₈H₂₂N₂O₅S
• 分子量: 378.449
• InChiKey: VENUDVIOKANLRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  86.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-methyl-N'-(1-(2,4,6-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 碘苯 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 5.0h， 生成 4-(1-(1-(2,4,6-trimethoxyphenyl)vinyl)-1H-indol-5-yl)morpholine
  参考文献：
  名称：

  Tandem One-Pot Palladium-Catalyzed Coupling of Hydrazones, Haloindoles, and Amines: Synthesis of Amino-N-vinylindoles and Their Effect on Human Colon Carcinoma Cells

  摘要：

  The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp(2)-N bonds were formed through two mechanistically distinct reactions using a single Pd(II)/Pd(0) catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.

  DOI：

  10.1021/jo501315q
• 作为产物：
  描述：

  2,4,6-三甲氧基苯乙酮 、 对甲苯磺酰肼 以 甲醇 为溶剂， 以89%的产率得到4-methyl-N'-(1-(2,4,6-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide
  参考文献：
  名称：

  微管蛋白聚合抑制剂异combretastatin A-4的氟扫描：设计，合成，分子建模和生物学评估

  摘要：

  合成了一系列基于异康他汀A-4的氟化衍生物的微管蛋白聚合抑制剂，目的是评估这些化合物对增殖活性的影响。氟原子的引入是在苯环上或在两个芳环之间的连接基上进行的。通过在对位（3i）引入二氟甲氧基并用两个氟原子（3m）取代连接基的两个质子，对iso CA-4进行修饰，生成了该系列中活性最高的化合物，IC 50值为0.15–2.2 nM（3i）和0.1–2 nM（3m）分别针对一组六种癌细胞系。与参考CA-4或iso CA-4相比，化合物3i和3m具有更大的抗增殖活性，氟基团的存在导致抗增殖活性的显着增强。分子对接研究表明，化合物3i和3m占据了微管蛋白的秋水仙碱结合位点。在人类非癌细胞中的细胞毒性评估表明，化合物3i和3m在静止的外周血淋巴细胞中实际上无效，并且可能对癌细胞具有选择性的抗增殖活性。对细胞周期分布和形态学微管组织的分析表明，化合物3m诱导了G 2 / M相阻滞，并极大地破坏了微管网络。

  DOI：

  10.1016/j.ejmech.2017.11.055

文献信息

• Csp²–N Bond Formation via Ligand-Free Pd-Catalyzed Oxidative Coupling Reaction of <i>N</i>-Tosylhydrazones and Indole Derivatives
  作者：Maxime Roche、Gilles Frison、Jean-Daniel Brion、Olivier Provot、Abdallah Hamze、Mouad Alami

  DOI：10.1021/jo401217x

  日期：2013.9.6

  system was found to promote the Csp2–N bond-forming reaction utilizing N-tosylhydrazones and N-H azoles. This process shows functional group tolerance; di-, tri-, and tetrasubstituted N-vinylazoles were obtained in high yields. Under the optimized conditions, the reaction proceeds with high stereoselectivity depending on the nature of the coupling partners.

  在一种新的合成N-乙烯基唑的方法中，发现无配体的钯催化体系可利用N-甲苯磺酰hydr和NH唑类促进Csp 2 -N键形成反应。此过程显示了功能组的容忍度；高产率地获得了二，三和四取代的N-乙烯基唑。在最佳条件下，取决于偶合体的性质，反应以高的立体选择性进行。
• Water‐Facilitated Nitromethane‐Mediated Cyclization of 2‐(Phenylvinyl)benzhydrols: Access to 1,3‐Diphenyl‐1H‐indenes with Antitumor Activity
  作者：Camille Hauguel、Christine Tran、Olivier Provot、Jérôme Bignon、Vincent Gandon、Abdallah Hamze

  DOI：10.1002/adsc.202200550

  日期：2022.9.6

  This work reports a mild and operationally accessible method for synthesizing 1,3-diphenyl-1H-indene derivatives from N-tosylhydrazones and bromobenzhydrols as readily available reactants. Moreover, the cyclization step does not require metal catalysis, the addition of an acid, or a very high temperature. We report a combined experimental and computational study on the mechanism of this cyclization

  这项工作报告了一种温和且可操作的方法，用于从N-甲苯磺酰腙和溴苯甲醇作为容易获得的反应物合成 1,3-二苯基-1H-茚衍生物。此外，环化步骤不需要金属催化、添加酸或非常高的温度。我们报告了关于这种环化机制的实验和计算研究。此外，我们通过合成大量产品（甚至是克级产品）以及获得新的生物学相关分子来证明这种方法的实用性。
• Synthesis of substituted benzylboronates by light promoted homologation of boronic acids with <i>N</i>-sulfonylhydrazones
  作者：Álvaro Valdés-Maqueda、Lucía López、Manuel Plaza、Carlos Valdés

  DOI：10.1039/d3sc05678c

  日期：——

  and the pinacolboronates can be isolated after reaction of the benzylboronic acid with pinacol. The metholodogy has been applied to the reactions of alkylboronic acids with N-tosylhydrazones of aromatic aldehydes and ketones, and to the reactions of arylboronic acids with N-tosylhydrazones of aliphatic ketones. Moreover, the employment of the DBU/DIPEA bases combination allows for homogeneous reactions

  描述了在碱性条件下通过硼酸与N-甲苯磺酰腙的光化学同系化合成苄基硼酸酯。该反应涉及N-甲苯磺酰腙盐的光解以产生重氮烷，然后进行重氮烷的偕碳硼化。在温和的反应条件下，避免了不稳定的苄基硼酸的先脱硼，并且在苄基硼酸与频哪醇反应后可以分离出频哪醇硼酸酯。该方法已应用于烷基硼酸与芳香醛和酮的N-甲苯磺酰腙的反应，以及芳基硼酸与脂肪族酮的N-甲苯磺酰腙的反应。此外，DBU/DIPEA 碱组合的使用允许进行均相反应，该反应已适应光化学连续流动条件。此外，硼酸酯的合成多功能性使其能够通过Csp 3 –C 或 Csp 3 –X 键形成反应进一步转化，从而将该方法转化为一种通过 N-甲苯磺酰腙对羰基进行偕双官能化的新方法。
• Copper Acetoacetonate [Cu(acac)₂]/BINAP-Promoted C<i>sp</i>³N Bond Formation<i>via</i>Reductive Coupling of<i>N</i>-Tosylhydrazones with Anilines
  作者：Jessy Aziz、Jean-Daniel Brion、Abdallah Hamze、Mouad Alami

  DOI：10.1002/adsc.201300466

  日期：2013.8.12

  AbstractWe report the the copper(II) acetoacetonate [Cu(acac)2]/BINAP‐catalyzed synthesis of arylamines from N‐tosylhydrazones and anilines. A fine tuning of the reaction conditions was required to accomplish the cross‐coupling successfully, including the ligands effect and the addition of small amounts of water. The characteristic feature of this protocol is its functional group compatibility and its chemoselectivity when various aminophenol derivatives were used. Taking into consideration the interest for this copper‐reductive coupling in which no stoichiometric metal hydride reagent is employed, this can be considered as an alternative to the conventional reductive amination.magnified image
• Catalytic Three-Component One-Pot Reaction of Hydrazones, Dihaloarenes, and Amines
  作者：Maxime Roche、Abdallah Hamze、Jean-Daniel Brion、Mouad Alami

  DOI：10.1021/ol303194s

  日期：2013.1.4

  A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and various primary and secondary amines was devised, producing nitrogen-containing 1,1'-diarylethylenes in good yields. The two C-C and C-N bonds formed through this coupling have been catalyzed by a single Pd-catalyst in a one-pot fashion.