(E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-4-methylbenzenesulfonamide | 135822-89-8

• 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: (E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-4-methylbenzenesulfonamide
• 英文别名: (NE)-N-(1,3-benzodioxol-5-ylmethylidene)-4-methylbenzenesulfonamide
• CAS: 135822-89-8
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: FAAORLFQSDBSJE-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-4-methylbenzenesulfonamide 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 2-Benzo[1,3]dioxol-5-yl-1-(toluene-4-sulfonyl)-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines:  A Convenient Synthesis of Pentabromopseudilin

  摘要：

  The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates or 2-butynoates with an appropriate phosphine as the catalyst, toward the electron deficient imines is described. Triphenylphosphine-catalyzed reaction of-methyl a,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A:reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

  DOI：

  10.1021/jo9723063
• 作为产物：
  描述：

  N-[1,3-benzodioxol-5-yl-(4-methylphenyl)sulfonylmethyl]-4-methylbenzenesulfonamide 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(E)-N-(benzo[d][1,3]dioxol-5-ylmethylene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Practical and General Entry toN‐Tosyl Aryl Aldimines Promoted by Sulfamic Acid in Water and Alcohol

  摘要：

  A practical, indirect procedure composed of a three-component condensation using aromatic aldehydes, p-tosylamide, and sodium p-toluenesulfinate in the presence of sulfamic acid in tap water-alcohol solvents to afford amidosulfones, and the subsequent water two-phase basic elimination of the amidosulfones to N-tosyl arylimines, was developed. The process has little environmental impact, easy workup, mild reaction conditions, and good yields and is amenable to large-scale preparations.

  DOI：

  10.1080/00397910601131387

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。
• Development and Pharmacological Characterization of Selective Blockers of 2-Arachidonoyl Glycerol Degradation with Efficacy in Rodent Models of Multiple Sclerosis and Pain
  作者：Margherita Brindisi、Samuele Maramai、Sandra Gemma、Simone Brogi、Alessandro Grillo、Lorenzo Di Cesare Mannelli、Emanuele Gabellieri、Stefania Lamponi、Simona Saponara、Beatrice Gorelli、Daniele Tedesco、Tommaso Bonfiglio、Christophe Landry、Kwang-Mook Jung、Andrea Armirotti、Livio Luongo、Alessia Ligresti、Fabiana Piscitelli、Carlo Bertucci、Marie-Pierre Dehouck、Giuseppe Campiani、Sabatino Maione、Carla Ghelardini、Anna Pittaluga、Daniele Piomelli、Vincenzo Di Marzo、Stefania Butini

  DOI：10.1021/acs.jmedchem.5b01812

  日期：2016.3.24

  action, high membrane permeability, high brain penetration evaluated using a human in vitro blood–brain barrier model, high selectivity in binding and affinity-based proteomic profiling assays, and low in vitro toxicity. Mode-of-action studies demonstrate that 4a, by blocking MGL, increases 2-arachidonoylglycerol and behaves as a cannabinoid (CB1/CB2) receptor indirect agonist. Administration of 4a in

  我们报告了化合物4a的发现，该化合物是一种有效的基于β-内酰胺的单酰基甘油脂肪酶（MGL）抑制剂，其特征在于使用人类体外血脑屏障模型评估了不可逆和立体选择性的作用机制，高膜通透性和高脑渗透性，在基于结合和亲和力的蛋白质组分析中具有很高的选择性，并且在体外具有较低的毒性。作用模式研究表明4a通过阻断MGL可以增加2-花生四烯酸甘油酯，并具有大麻素（CB1 / CB2）受体间接激动剂的作用。在患有实验性自身免疫性脑炎的小鼠中给予4a可以改善CB1 / CB2依赖性的临床症状。而且4a在啮齿动物的急性炎性疼痛模型中产生了镇痛作用，该模型被CB1和CB2受体拮抗剂/反向激动剂所拮抗。4a还减轻了由奥沙利铂引起的神经性超敏反应。鉴于这些证据，作为MGL选择性抑制剂的4a可能代表了多发性硬化症和慢性疼痛的治疗选择的未来发展的有价值的线索。
• Silica-supported Zinc Chloride (ZnCl2/SiO2)-induced Efficient Protocol for the Synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
  作者：Hanan A. Soliman、Mahmoud El-Shahat、Abdel-Ghany Soliman

  DOI：10.2174/1570178615666181025120307

  日期：2019.5.30

  straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages

  已开发出一种简单的策略，可在无溶剂条件下，利用二氧化硅负载的氯化锌（ZnCl2 / SiO2，silzic）作为催化剂，由磺酰胺和芳基醛合成N-磺酰基亚胺衍生物。在相同条件下，2-氨基苯硫酚与芳基醛的反应也可以合成2-芳基苯并噻唑衍生物。该方法具有产率高，反应条件温和，方法简单，成本低和后处理简单的优点。该催化剂在重复使用方面具有相同的效率，最高可达三倍。
• Highly diastereoselective Mannich-type reaction of titanium enolate derived from 2′-hydroxypropiophenone
  作者：Guisheng Deng、Honghua Mo、Jing Luo、Jingyuan Zou

  DOI：10.1139/v2012-027

  日期：2012.6

  N-tosylimines. Noteworthy is the observation that the influence of a second Lewis acid on the Mannich-type reaction based on the titanium enolate is opposite to that obtained from other titanium enolates reported. A reasonable mechanism has been proposed to explain the high anti diastereoselectivity and the effect of a second Lewis acid on yield.

  从 2'-羟基苯丙酮衍生的钛烯醇化物与 N-甲苯磺酰亚胺的曼尼希型加成提供了相应的 β-氨基酮，产率良好至极好 (60%–90%)，并且具有 >99: <1 的抗非对映选择性。已经开发了一种基于钛烯醇化物合成抗 β-氨基酮作为主要异构体的模型。高抗选择性与 N-甲苯磺酰亚胺苯环上的给电子和吸电子基团无关。值得注意的是，第二个路易斯酸对基于钛烯醇化物的曼尼希型反应的影响与报道的其他钛烯醇化物相反。已经提出了一种合理的机制来解释高抗非对映选择性和第二种路易斯酸对产率的影响。
• Highly Enantioselective Aza-Henry Reaction of <i>N</i>-Tosyl Imines Catalyzed by <i>N,N</i>‘-Dioxide−Cu(I) Complexes
  作者：Hui Zhou、Dan Peng、Bo Qin、Zongrui Hou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/jo702200u

  日期：2007.12.1

  The N,N‘-dioxide−Cu(I) complexes have been developed to catalyze the addition of nitromethane to N-tosyl aldimines. The aza-Henry reaction proceeds smoothly affording the corresponding nitro amines in good yields with high enantioselectivities. A catalytic cycle is proposed to explain the origin of reactivity.

  该ñ，ñ “二氧化物-铜（I）配合物已发展到催化将硝基甲烷来ñ甲苯磺酰亚胺。氮杂-亨利反应平稳进行，以高收率和高对映选择性提供相应的硝基胺。建议使用催化循环来解释反应性的起源。