2-(benzylamino)-4-(tert-butyl)phenol | 107235-52-9

• 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-(benzylamino)-4-(tert-butyl)phenol
• 英文别名: 2-phenylmethylamino-4-tert-butylphenol；2-(Benzylamino)-4-tert-butylphenol
• CAS: 107235-52-9
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: AHMPJRGZEUYFTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzylamino)-4-(tert-butyl)phenol 在 氧气 、 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以100%的产率得到5-(tert-butyl)-2-phenylbenzoxazole
  参考文献：
  名称：

  Oxidative transformation of N-substituted 2-aminophenols to 2-substituted benzoxazoles catalyzed by polymer-incarcerated and carbon-stabilized platinum nanoclusters

  摘要：

  通过在聚合物/炭黑复合材料上负载的铂纳米簇催化的N-取代-2-氨基酚的顺序氧化-烯醇化-氧化环化反应，实现了2-取代苯并噁唑的制备。

  DOI：

  10.1139/v11-161
• 作为产物：
  描述：

  2-氨基-4-叔丁基酚 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 2-(benzylamino)-4-(tert-butyl)phenol
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of New N-(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

  摘要：

  Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

  DOI：

  10.1021/acs.jmedchem.7b01312

文献信息

• Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst
  作者：Amreen K. Bains、Abhishek Kundu、Sudha Yadav、Debashis Adhikari

  DOI：10.1021/acscatal.9b02977

  日期：2019.10.4

  bench-stable azo-phenolate ligand-coordinated nickel catalyst which can efficiently execute N-alkylation of a variety of anilines by alcohol. We demonstrate that the redox-active azo ligand can store hydrogen generated during alcohol oxidation and redelivers the same to an in-situ-generated imine bond to result in N-alkylation of amines. The reaction has wide scope, and a large array of alcohols can directly

  我们在这里报道了一种定义明确且稳定的偶氮酚盐配体配位的镍催化剂，该催化剂可以通过醇有效地进行多种苯胺的N-烷基化。我们证明，氧化还原活性偶氮配体可以存储在醇氧化过程中产生的氢，并将其重新转移到原位产生的亚胺键上，从而导致胺的N-烷基化。该反应的范围很广，并且大量的醇可以直接偶联到各种苯胺上。包括氘标记到基质上的机理研究建立了从醇中借用氢的方法，并指出了存在于配体主链上的氧化还原活性偶氮部分的关键作用。用自由基猝灭剂和更高的k H / k分离捕获形式的酮基中间体醇氧化步骤的D建议将氢原子转移（HAT）完全转移到还原的偶氮主链上，以铺平醇氧化，这与常规的金属-配体双功能机理相反。该实施例清楚地表明，廉价的贱金属催化剂可以在氧化还原活性配体主链的帮助下完成重要的偶联反应。
• One‐Pot Cascade Transformation of Glucal into Structurally Diverse Drug‐Like Scaffolds
  作者：Hui Yao、Ronny Willam、Siming Wang、Jingxi He、Tai Guo、Xue‐Wei Liu

  DOI：10.1002/asia.201900844

  日期：2019.11.18

  A diversity-oriented synthesis strategy to produce three types of structurally drug-like N-heterocyclic-fused rings has been developed from abundant biomass-derived d-glucal, aniline and water in a stereoselective manner. The overall transformation which entails a cascade of Ferrier reaction and 4π conrotatory imino-Nazarov cyclization was performed in one-pot allowing convenient preparation of scaffolds

  已经从丰富的生物质衍生的d-葡萄糖，苯胺和水中以立体选择性的方式开发了以多样性为导向的合成策略，该策略可生产三种类型的结构类似药物的N-杂环稠合环。整个转化过程包括一级费雷尔反应和4π旋转亚氨基-纳扎罗夫环化反应，可在一锅中完成，从而可以从相对简单的起始原料方便地制备具有高分子复杂性的支架。尽管使用邻位未取代的仲苯胺作为底物很容易获得二氢吲哚稠合的产物，但与邻羟基苯胺的反应却提供了稠合的1,4-苯并恶嗪。在这两种情况下，InBr3都充当路易斯酸催化剂。通过将InBr3更改为Ln（OTf）3，
• Anti-allergic or anti-inflammatory substituted (hetero)-aralkylamino-ortho-phenols
  申请人：BEECHAM GROUP PLC

  公开号：EP0200345A2

  公开（公告）日：1986-12-10

  Compounds of the general formula (I) or a pharmaceutically acceptable salt or solvate thereof; wherein R, is straight or branched C1-6 alkyl, halo, nitro, cyano, hydroxy, or COR6 wherein R6 is straight or branched C1-6 alkyl or aryl, R2 is substituted or unsubstituted aryl, aralkyl or heteroaryl; R3 is hydrogen or straight or branched C1-6alkyl; R4 is hydrogen, hydroxy, straight or branched C1-6 alkyl, halo, nitro, cyano, C1-6 alkoxy, halo(C1-6)alkyl; amino, carboxylic ester, carboxylic acid, COR6,SR6, SO2R6, NHCOR6 or NHR6 wherein R6 is as defined above; and R5 is hydrogen, straight or branched C1-6 alkyl, substituted or unsubstituted benzyl or COR6 wherein R6 is as defined above; are of value in the prophylaxis and treatment of allergic and inflammatory disorders.

  通式(I)化合物 或其药学上可接受的盐或溶液； 其中 R 是直链或支链 C1-6 烷基、卤素、硝基、氰基、羟基或 COR6，其中 R6 是直链或支链 C1-6 烷基或芳基、 R2 是取代或未取代的芳基、芳烷基或杂芳基； R3 是氢或直链或支链 C1-6 烷基； R4 是氢、羟基、直链或支链 C1-6 烷基、卤代、硝基、氰基、C1-6 烷氧基、卤代（C1-6）烷基；氨基、羧酸酯、羧酸、COR6、SR6、SO2R6、NHCOR6 或 NHR6，其中 R6 如上定义；以及 R5 是氢、直链或支链 C1-6 烷基、取代或未取代的苄基或 COR6，其中 R6 如上文所定义； 具有预防和治疗过敏性和炎症性疾病的价值。 对预防和治疗过敏性和炎症性疾病有价值。
• Design, Synthesis, and Biological Activity of New <i>N</i>-(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension
  作者：Morane Le Hiress、Bernardin Akagah、Guillaume Bernadat、Ly Tu、Raphaël Thuillet、Alice Huertas、Carole Phan、Elie Fadel、Gérald Simonneau、Marc Humbert、Gaël Jalce、Christophe Guignabert

  DOI：10.1021/acs.jmedchem.7b01312

  日期：2018.4.12

  Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.
• Oxidative transformation of N-substituted 2-aminophenols to 2-substituted benzoxazoles catalyzed by polymer-incarcerated and carbon-stabilized platinum nanoclusters
  作者：Woo-Jin Yoo、Hao Yuan、Hiroyuki Miyamura、Shū Kobayashi

  DOI：10.1139/v11-161

  日期：2012.3

  The preparation of 2-substituted benzoxazoles was achieved through a sequential aerobic oxidation – enolization – oxidative cyclization reaction of N-substituted 2-aminophenols catalyzed by platinum nanoclusters supported on a polymer / carbon black composite material.

  通过在聚合物/炭黑复合材料上负载的铂纳米簇催化的N-取代-2-氨基酚的顺序氧化-烯醇化-氧化环化反应，实现了2-取代苯并噁唑的制备。