N-(2-hydroxynaphthalen-1-yl)-methylene-4-methylbenzenesulfonamide | 314248-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxynaphthalen-1-yl)-methylene-4-methylbenzenesulfonamide
• 英文别名: N-[(2-hydroxy-1-naphthyl)methylene]-4-methylbenzenesulfonamide；N-(2-Hydroxy-1-naphthylmethylene)-p-toluenesulfonamide；N-[(2-hydroxynaphthalen-1-yl)methylidene]-4-methylbenzenesulfonamide
• CAS: 314248-24-3
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: WCYGPLQLYOSVIH-UHFFFAOYSA-N

物化性质

• 沸点：
  540.3±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  4

制备方法与用途

生物活性方面，COH34 类似物 1（一种代谢产物）是 COH34 的氧化衍生物。COH34 是一个高效的多聚(ADP-核糖)糖基水解酶（PARG）抑制剂。

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxynaphthalen-1-yl)-methylene-4-methylbenzenesulfonamide 、 3-丁炔-2-酮 在 三乙烯二胺 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以74%的产率得到N-(2-acetyl-1H-benzo[f]-chromen-1-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  通过DABCO催化的丁-3-炔-2-酮和丙酸甲酯与水杨基N-甲苯磺酰亚胺（DABCO = 1,4-二氮杂双环[2.2.2]辛烷）的反应合成取代的色烯。

  摘要：

  DA-3-CO-2-丁-3-甲基-2-酮和丙炔酸甲酯与水杨基N-甲苯磺胺酯的DABCO催化（DABCO = 1,4-二氮杂双环[2.2.2]辛烷）反应可生成高度官能化的色烯，并进行了深入研究。在1H NMR光谱学的基础上已经证明了该反应的合理机理。

  DOI：

  10.1002/chem.200501291

文献信息

• Highly efficient synthesis of 9-aminoxanthenes via the tandem reaction of arynes with salicyl N-tosylimines
  作者：Lin He、Ji Xin Pian、Jing Zhang、Yuan Zhen Li

  DOI：10.1016/j.cclet.2012.11.008

  日期：2012.12

  A cascade insertion–nucleophilic annulation reaction of salicyl N-tosylimines with aryne generated in situ from 2-(trimethylsilyl) aryl triflate and KF-18-crown-6 has been developed, providing 9-aminoxanthenes efficiently in one step.

  已经开发了水杨酸N-甲苯磺胺类化合物与三氟甲磺酸2-（三甲基甲硅烷基）芳基酯和KF-18-crown-6原位生成的芳烃的级联插入-亲核环化反应，可一步有效地提供9-氨基黄嘌呤。
• Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles
  作者：Xing Liu、Daqian Wang、Jing Sun、Chao-Guo Yan

  DOI：10.1016/j.molstruc.2024.137684

  日期：2024.5

  forward synthetic protocol for spiro and fused chromenes has been developed by base promoted oxa-Michael/Mannich reaction of salicyl N-tosylimines and various cyclic dienophiles. 1,4-diazabicyclo[2.2.2]octane (DABCO) promoted [4 + 2] cycloaddition reaction of salicyl N-tosylimines and 3-methyleneoxindoles or 2-arylidene-1,3-indanediones in THF at room temperature afforded functionalized spiro[chromane-3,3′-indolines]

  通过水杨酰 N-甲苯磺酰亚胺和各种环状嗜二烯烃的碱促进 oxa-Michael/Mannich 反应，开发了一种直接的螺和熔融铬合成方案。1,4-二氮杂双环[2.2.2]辛烷 （DABCO） 在室温下促进水杨基 N-甲苯磺酰亚胺和 3-亚甲基氧吲哚或 2-芳基-1,3-茚二酮在 THF 中的[4 + 2]环加成反应，得到功能化螺[色烷-3,3′-吲哚啉]或螺[chromane-3,2′-inden]-1′，3′-二酮，中等至良好产率和高非对映选择性。另一方面，水杨酰 N-甲苯磺酰亚胺和 5,6-未取代的 1,4-二氢吡啶的类似 [4 + 2] 环加成反应导致四氢铬基 [3,2-b] 吡啶衍生物的产率令人满意。
• Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes
  作者：Chong-Dao Lu、Shan-Shan Lu

  DOI：10.1055/s-0032-1318311

  日期：——

  An efficient synthesis of N-(9-xanthyl)-4-toluenesulfonamides is described in which salicyl N-tosylimines react with silylaryl triflates in the presence of CsF. This mild process involves an addition-cyclization cascade in which arynes are generated and trapped in situ.
• Three-Component Coupling Reaction and Cyclization of <i>N</i>-Tosylimines and TMS-Substituted Propiolate Mediated by DABCO
  作者：Yuji Matsuya、Kousuke Hayashi、Akiho Wada、Hideo Nemoto

  DOI：10.1021/jo702649q

  日期：2008.3.1

  [GRAPHICS]A new three-component coupling reaction of methyl 3-trimethylsilylpropiolate, N-tosylimine, and tosylamide mediated by DABCO was developed. This reaction was based on the consecutive alpha- and beta-activation method of propiolate involving intramolecular silyl migration previously developed by our group. On the basis of these results, a new cyclization reaction was designed to find a chrome ne-formin g reaction utilizing salicyl N-tosylimine as a bifunctional substrate.
• Synthesis of Substituted Chromenes through the DABCO-Catalyzed Reaction of But-3-yn-2-one and Methyl Propiolate with SalicylN-Tosylimines (DABCO=1,4-diazabicyclo[2.2.2]octane)
  作者：Yong-Ling Shi、Min Shi

  DOI：10.1002/chem.200501291

  日期：2006.4.12

  The DABCO-catalyzed (DABCO = 1,4-diazabicyclo[2.2.2]octane) reaction of but-3-yn-2-one and methyl propiolate with salicyl N-tosylimines yields highly functionalized chromenes and has been thoroughly investigated; the rational mechanism for the reaction has been demonstrated on the basis of 1H NMR spectroscopic investigation.

  DA-3-CO-2-丁-3-甲基-2-酮和丙炔酸甲酯与水杨基N-甲苯磺胺酯的DABCO催化（DABCO = 1,4-二氮杂双环[2.2.2]辛烷）反应可生成高度官能化的色烯，并进行了深入研究。在1H NMR光谱学的基础上已经证明了该反应的合理机理。