4-methoxy-N-(4-(methylsulfonyl)benzylidene)aniline | 197905-49-0

• 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-methoxy-N-(4-(methylsulfonyl)benzylidene)aniline
• 英文别名: 4-Methoxy-N-(4-methylsulfonylbenzylidene)aniline；N-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)methanimine
• CAS: 197905-49-0
• 化学式: C₁₅H₁₅NO₃S
• 分子量: 289.355
• InChiKey: XUSKQNHHQFTLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(4-(methylsulfonyl)benzylidene)aniline 在 三氯硅烷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 以91%的产率得到N-(4′-methanesulfonyl)benzyl-4-methoxy-aniline
  参考文献：
  名称：

  再论还原胺化：二甲基甲酰胺催化三氯硅烷还原醛亚胺——官能团的耐受性、范围和限制

  摘要：

  在二甲基甲酰胺 (DMF) 作为有机催化剂 (≤10 mol%) 的甲苯或CH 2 Cl 2在室温下。还原耐受酮羰基、酯、酰胺、腈、砜、磺酰胺、NO 2、SF 5和CF 3基团、硼酸酯、叠氮化物、氧化膦、C=C和C≡C键和二茂铁核，但亚砜和ñ -oxides降低。α,β-不饱和醛亚胺仅进行 1,2-还原，使 C=C 键保持完整。ñ- 伯胺的单烷基化以 1:1 的醛与胺的比例实现，而过量的醛 (≥2:1) 允许第二次烷基化，产生叔胺。α-氨基酸的还原性N-烷基化在没有外消旋作用的情况下进行；所得产物含有 C≡C 键或 N 3基团，适用于点击化学。因此，该反应在效率和化学选择性方面优于传统方法（硼氢化物还原或催化氢化）。一些反应伙伴的溶解度似乎是唯一的限制。使用 NaHCO 3水溶液（即 NaCl 和二氧化硅）后处理产生的副产物对环境无害。作为一种更环保的替代品，DMA 可以代替 DMF 用作催化剂。

  DOI：

  10.1021/acs.joc.1c01561
• 作为产物：
  描述：

  N-(p-Methylmercaptobenzal)-p-anisidin 在 potassium peroxymonosulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 4-methoxy-N-(4-(methylsulfonyl)benzylidene)aniline
  参考文献：
  名称：

  Analogue-based design, synthesis and docking of non-steroidal anti-inflammatory agents. Part 2: Methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-ones

  摘要：

  A series of methyl sulfanyl/methyl sufonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one were designed using analogue-based design, scaffold hopping and shape similarity matching. The designed compounds were synthesized in 2-3 steps with simple chemistry and screened by ovine cyclooxygenases (COXs) inhibitory assay and carrageenan-induced rat paw edema assay. Among the screened compounds, two compounds exhibited 100% cyclooxygenase-2 (COX-2) inhibitory potency without showing cycloxygenase-1 (COX-1) inhibition at 20 mu M. The compounds also showed promising in vivo anti-inflammatory potential. A structure-activity relationship within the dataset was established by correlating the effect of aromatic ring substituent constants, structural variables and physico-chemical descriptors with in vivo anti-inflammatory activity. Molecular docking studies were also performed on the title compounds to study the binding interactions to COX-2 active site residues. The experimentally determined COX-2 inhibitory activity was found moderately correlating with binding modes predicted for compounds by Glide XP dock scoring function. The 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one pharmacophore reported herein should be a new lead for further development of novel non-steroidal anti-inflammatory agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.069

文献信息

• Stereoselective Olefination and Regiospecific Vicinal Difunctionalization of Imines with α-(Benzothiazol-2-ylsulfonyl) Carbonyl Compounds
  作者：You-Dong Shao、Xue-Song Wu、Shi-Kai Tian

  DOI：10.1002/ejoc.201101684

  日期：2012.3

  Depending on their structures, imines are able to undergo either olefination or vicinal difunctionalization with various α-(benzothiazol-2-ylsulfonyl) carbonyl compounds in the absence of external bases. The olefination reaction of aromatic imines with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds proceeds smoothly in tetrahydrofuran at 70 °C to give structurally diverse α,β-unsaturated esters,

  根据它们的结构，亚胺能够在没有外部碱的情况下与各种 α-(苯并噻唑-2-基磺酰基)羰基化合物进行烯化或邻位双官能化。芳族亚胺与 α-(苯并噻唑-2-基磺酰基)羰基化合物的烯化反应在四氢呋喃中在 70°C 下顺利进行，得到结构多样的 α,β-不饱和酯、酰胺和酮，收率良好至极好，并且具有极高的产率(E) 选择性。相比之下，环状亚胺的碳-氮双键和 α,β-不饱和亚胺的碳-碳双键在相同的反应条件下与 α-(苯并噻唑-2-基磺酰基)羰基化合物进行区域特异性邻位双官能化，以良好到极好的收率提供各种苯并噻唑衍生物。值得注意的是，苯并噻唑部分存在于许多抗肿瘤剂和生物发光分子中。此外，已经提出了合理的反应途径来解释这些转变，并且这些反应得到了反应混合物的 ESI-MS 分析的充分支持。
• Design, synthesis, and biological evaluation of new 1,4‐diarylazetidin‐2‐one derivatives (β‐lactams) as selective cyclooxygenase‐2 inhibitors
  作者：Hadi Arefi、Nima Naderi、Amir B. Irani Shemirani、Mina Kiani Falavarjani、Mahsa Azami Movahed、Afshin Zarghi

  DOI：10.1002/ardp.201900293

  日期：2020.3

  A new series of 1,4‐diarylazetidin‐2‐one derivatives (β‐lactams) were designed and synthesized to evaluate their biological activities as selective cyclooxygenase‐2 (COX‐2) inhibitors. In vitro COX‐1 and COX‐2 inhibition studies showed that all compounds were selective inhibitors of the COX‐2 isozyme with IC50 values in the 0.05–0.11 µM range, and COX‐2 selectivity indexes in the range of 170–703.7

  设计并合成了一系列新的 1,4-二芳基氮杂环丁烷-2-one 衍生物（β-内酰胺类），以评估其作为选择性环氧合酶-2（COX-2）抑制剂的生物活性。体外 COX-1 和 COX-2 抑制研究表明，所有化合物都是 COX-2 同工酶的选择性抑制剂，IC50 值在 0.05-0.11 µM 范围内，COX-2 选择性指数在 170-703.7 范围内。在合成的β-内酰胺类中，3-甲氧基-4-(4-(甲基磺酰基)苯基)-1-(3,4,5-三甲氧基苯基)氮杂环丁烷-2-酮(4j)在N-1苯基上具有三甲氧基环表现出最高的 COX-2 抑制选择性和效力，甚至比参考药物塞来昔布更有效。还使用福尔马林试验测定合成化合物的镇痛活性。化合物4f在合成的分子中表现出最好的镇痛活性。分子模型研究表明，甲基磺酰基药效团可以插入到 COX-2 活性位点的二级口袋中，与 Arg513 相互作用。获得的结构-活性数据表明
• Ni-Catalyzed Coupling of Butadiene, Aldimines, and Arylboronic Acids to Homoallylic Amines under Base-Free Conditions
  作者：Yu-Qing Li、Shi-Liang Shi

  DOI：10.1021/acs.organomet.1c00096

  日期：2021.7.26

  three-component coupling of butadiene, aldimines, and arylboronic acids to form synthetically important homoallylic amines. The starting materials are stable and readily available; especially, butadiene is an abundant chemical feedstock. This protocol provides rapid access to various (E)-homoallylic amines with excellent regio- and stereoselectivity by constructing two C–C bonds simultaneously. The mild

  在此，我们报告了镍催化的丁二烯、醛亚胺和芳基硼酸的三组分偶联，以形成合成重要的高烯丙基胺。原料稳定且容易获得；尤其是丁二烯是一种丰富的化学原料。该协议通过同时构建两个 C-C 键，提供了对具有出色区域和立体选择性的各种 ( E )-高烯丙基胺的快速访问。温和且无碱的反应条件为醛亚胺和芳基硼酸偶联部分提供了广泛的底物范围和高官能团耐受性。
• 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic
  申请人：Sankyo Company, Limited

  公开号：US05908858A1

  公开（公告）日：1999-06-01

  Compounds of formula (I) and (II): ##STR1## \x9bwherein R is hydrogen, halogen or alkyl; R.sup.1 is alkyl, amino or substituted amino; R.sup.2 is optionally substituted phenyl; R.sup.3 is hydrogen, halogen or optionally substituted alkyl; R.sup.4 is hydrogen, optionally substituted alkyl, cycloalkyl, aryl, or aralkyl! have valuable analgesic, anti-inflammatory, anti-pyretic and anti-allergic activities and have the ability to inhibit the production of leukotrienes and to inhibit bone resorption. They are relatively free from the side effects which generally result from the administration of compounds having these kinds of activities.

  式(I)和(II)的化合物：##STR1## 其中R为氢、卤素或烷基；R.sup.1为烷基、氨基或取代氨基；R.sup.2为可选取代的苯基；R.sup.3为氢、卤素或可选取代的烷基；R.sup.4为氢、可选取代的烷基、环烷基、芳基或芳基烷基！具有有价值的镇痛、抗炎、退烧和抗过敏活性，并具有抑制白三烯产生和抑制骨吸收的能力。它们相对于一般具有这些活性的化合物的副作用较少。
• Regiodivergent C−H Annulation of Imines with Unsymmetrical Alkynes Using Transient Directing Alcohols via Rh(III) Catalysis
  作者：Bairong Liu、Yabo Chen、Qixin Liang、Yuyao Liang、Bifu Liu、Yuan Liu、Yang Gao、Qian Chen、Yanping Huo、Xianwei Li

  DOI：10.1002/adsc.202300167

  日期：2023.6.20

  Regiodivergent [3+2] and [4+2] C−H annulation of imines and imidate esters with unsymmetrical alkynes has been achieved under Rh(III) catalysis. Further transformation of the aldehyde and TMS functionality on the indene products is also demonstrated. The current work highlights the alcohols-directed multiple C−H annulation of imines and imidate esters, leading to diverse fused heterocycles.

  在 Rh(III) 催化下，亚胺和亚氨酸酯与不对称炔烃发生区域发散的 [3+2] 和 [4+2] C−H 环化。还展示了茚产品上醛和 TMS 官能团的进一步转化。目前的工作强调了醇引导的亚胺和亚氨酸酯的多个 C−H 环化，从而产生多种稠合杂环。