N-(p-Methylmercaptobenzal)-p-anisidin | 22116-70-7

• 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: N-(p-Methylmercaptobenzal)-p-anisidin
• 英文别名: N-(4-methoxyphenyl)-1-(4-methylsulfanylphenyl)methanimine
• CAS: 22116-70-7
• 化学式: C₁₅H₁₅NOS
• 分子量: 257.356
• InChiKey: ZMEXCKBDMNALDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 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：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲氧苯胺 、 4-(甲基巯基)苯甲醛 以 甲醇 为溶剂， 生成 N-(p-Methylmercaptobenzal)-p-anisidin
  参考文献：
  名称：

  1-氨基戊二烯基阳离子的间断Imino-Nazarov环化反应及相关的级联过程

  摘要：

  在催化量的路易斯酸存在下，由醛和仲苯胺缩合生成的1-氨基戊二烯基阳离子的4π易旋转亚氨基纳扎罗夫环化反应已得到开发。银（I）催化的分子内芳烃的捕获导致环氧基烯丙基阳离子的捕获导致三环吲哚啉稠合的环戊酮的形成。镧系元素盐的使用可在初始捕获后进行转化，从而以简洁的方式提供四氢喹啉融合的环戊烯酮。

  DOI：

  10.1002/anie.201405251

文献信息

• Allylic C(sp³)–H alkylation <i>via</i> synergistic organo- and photoredox catalyzed radical addition to imines
  作者：Jiaqi Jia、Rajesh Kancherla、Magnus Rueping、Long Huang

  DOI：10.1039/d0sc00819b

  日期：——

  A new catalytic method for the direct alkylation of allylic C(sp3)–H bonds from unactivated alkenes via synergistic organo- and photoredox catalysis is described. The transformation achieves an efficient, redox-neutral synthesis of homoallylamines with broad functional group tolerance, under very mild reaction conditions. Mechanistic investigations indicate that the reaction proceeds through the N-centered

  描述了一种新的催化方法，用于通过协同的有机和光氧化还原催化作用，使未活化烯烃中的烯丙基C（sp 3）-H键直接烷基化。该转化在非常温和的反应条件下实现了具有宽泛的官能团耐受性的高烯丙基胺的高效，氧化还原中性合成。机理研究表明该反应通过以N为中心的自由基中间体进行，该中间体是通过将烯丙基自由基加成至亚胺而产生的。
• Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations
  作者：Kirill K. Popov、Joanna L. P. Campbell、Ondřej Kysilka、Jan Hošek、Christopher D. Davies、Milan Pour、Pavel Kočovský

  DOI：10.1021/acs.joc.1c01561

  日期：2022.1.21

  Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalyst (≤10 mol %) in toluene or CH2Cl2 at room temperature. The reduction tolerates ketone carbonyls, esters, amides, nitriles, sulfones, sulfonamides, NO2

  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。
• 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。
• Aza-Diels–Alder reaction of Danishefsky's diene with immines catalyzed by porous α-zirconium hydrogen phosphate and SDS under solvent-free conditions
  作者：Francesca Bellezza、Antonio Cipiciani、Umberto Costantino、Francesco Fringuelli、Mara Orrù、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1016/j.cattod.2009.07.105

  日期：2010.7

  The aza-Diels–Alder reaction between benzaldimines 1 and Danishefsky's diene in solvent-free conditions is reported for the first time. The reaction occurs rapidly at 30 °C and is catalyzed by porous α-zirconium hydrogen phosphate (p-αZrP) in the presence of sodium dodecyl sulfate (SDS). The yields were excellent. The recycling of the catalyst has also been investigated.

  首次报道了在无溶剂条件下，苯甲二胺1与Danishefsky的二烯之间的aza-Diels-Alder反应。该反应在30°C下迅速发生，并在十二烷基硫酸钠（SDS）的存在下被多孔的磷酸氢锆锆（p-αZrP）催化。产量极好。还研究了催化剂的再循环。
• Direct Aza-Diels-Alder Reaction in Water Catalyzed by Layered α-Zirconium Hydrogen Phosphate and Sodium Dodecyl Sulfate
  作者：Umberto Costantino、Francesco Fringuelli、Mara Orrù、Morena Nocchetti、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1002/ejoc.200801132

  日期：2009.3

  The direct aza-Diels–Alder reaction between 2-cyclohexen-1-one (1) and benzaldimines 2 in water is reported for the first time. The reaction occurs at 30 °C, is catalyzed by layered α-zirconium hydrogen phosphate (α-ZrP) and requires the presence of sodium dodecyl sulfate (SDS). The reaction yield is excellent, the reaction is faster and the exo diastereoselectivity is higher than when organic solvent

  2-cyclohexen-1-one (1) 和苯二亚胺 2 在水中的直接 aza-Diels-Alder 反应是首次报道。该反应在 30 °C 下发生，由层状 α-磷酸氢锆 (α-ZrP) 催化，需要存在十二烷基硫酸钠 (SDS)。与使用有机溶剂相比，反应收率极好，反应速度更快，外非对映选择性更高。还研究了反应的一锅、三组分版本以及催化剂和含水母液（水、α-ZrP 和 SDS）的再循环。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)