2-fluorobenzyl 4-methylbenzenesulfonate

• 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: 2-fluorobenzyl 4-methylbenzenesulfonate
• 英文别名: 2-fluorobenzyl tosylate；(2-Fluorophenyl)methyl 4-methylbenzene-1-sulfonate；(2-fluorophenyl)methyl 4-methylbenzenesulfonate
• 化学式: C₁₄H₁₃FO₃S
• 分子量: 280.32
• InChiKey: YZHALSFOSIBELB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-fluorobenzyl 4-methylbenzenesulfonate 在 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-fluoro-2-(iodomethyl)benzene
  参考文献：
  名称：

  Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)

  摘要：

  The first one-pot deoxftyanamidation,of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diveite range of tertiary,cyanamides in excellent isolated yields. ThiS approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more Commonly employed for electrophilic C- and N-cyanation processes.

  DOI：

  10.1021/acs.orglett.7b01710
• 作为产物：
  描述：

  2-氟苄醇 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 以84%的产率得到2-fluorobenzyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)

  摘要：

  The first one-pot deoxftyanamidation,of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diveite range of tertiary,cyanamides in excellent isolated yields. ThiS approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more Commonly employed for electrophilic C- and N-cyanation processes.

  DOI：

  10.1021/acs.orglett.7b01710

文献信息

• Novel Dual-Acting Hybrids Targeting Type-2 Cannabinoid Receptors and Cholinesterase Activity Show Neuroprotective Effects In Vitro and Amelioration of Cognitive Impairment In Vivo
  作者：Claudia Mugnaini、Antonella Brizzi、Marco Paolino、Enrico Scarselli、Riccardo Castelli、Modesto de Candia、Nicola Gambacorta、Orazio Nicolotti、Magdalena Kostrzewa、Poulami Kumar、Ali Mokhtar Mahmoud、Vittoria Borgonetti、Monica Iannotta、Andrea Morace、Nicoletta Galeotti、Sabatino Maione、Cosimo D. Altomare、Alessia Ligresti、Federico Corelli

  DOI：10.1021/acschemneuro.3c00656

  日期：2024.3.6

  pharmacological effects in vitro and in vivo of dual-acting compounds that inhibit AChE and butyrylcholinesterase (BChE) and target CB2R. Within the investigated series, compound 4g proved to be the most promising. It achieved IC50 values in the low micromolar to submicromolar range against both human cholinesterase isoforms while antagonizing CB2R with Ki of 31 nM. Interestingly, 4g showed neuroprotective effects

  阿尔茨海默病（AD）是一种神经退行性痴呆，其特征是突触丧失和认知能力进行性下降。目前治疗AD的药物中，乙酰胆碱酯酶（AChE）抑制剂的疗效仅限于缓解症状，且副作用显着且依从性差。通过激活或阻断内源性大麻素系统 2 型大麻素受体 (CB2R) 活性的药物也被证明可以有效对抗神经炎症。在此，我们描述了抑制AChE和丁酰胆碱酯酶（BChE）并靶向CB2R的双重作用化合物的设计、合成和体外和体内药理作用。在所研究的系列中，化合物4g被证明是最有前途的。它对两种人胆碱酯酶亚型均达到低微摩尔至亚微摩尔范围内的 IC 50值，同时拮抗 CB2R， K i为 31 nM。有趣的是， 4g对 SH-SY5Y 细胞系显示出神经保护作用，因为它能够在体内 Y 迷宫强制交替试验中预防氧化应激诱导的细胞毒性并逆转东莨菪碱诱导的遗忘症。
• Deoxycyanamidation of Alcohols with <i>N</i>-Cyano-<i>N</i>-phenyl-<i>p</i>-methylbenzenesulfonamide (NCTS)
  作者：James N. Ayres、Matthew W. Ashford、Yannick Stöckl、Vassili Prudhomme、Kenneth B. Ling、James A. Platts、Louis C. Morrill

  DOI：10.1021/acs.orglett.7b01710

  日期：2017.7.21

  The first one-pot deoxftyanamidation,of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diveite range of tertiary,cyanamides in excellent isolated yields. ThiS approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more Commonly employed for electrophilic C- and N-cyanation processes.