2-benzylamino-3-methylphenol | 1414358-22-7

• 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: 2-benzylamino-3-methylphenol
• 英文别名: 2-(Benzylamino)-3-methylphenol；2-(benzylamino)-3-methylphenol
• CAS: 1414358-22-7
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: UFIUXBSEQAMYSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-3-methylphenol 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 4.0h， 生成 (±)-4-benzyl-2-hydroxy-5-methyl-2-phenyl-2H-benzo[b][1,4]oxazin-3(4H)-one
  参考文献：
  名称：

  10.1002/anie.202402908

  摘要：

  The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra‐substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea‐catalysed acylative DKR of tetra‐substituted morpholinone and benzoxazinone‐derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89%, 99:1 er) observed across a broad range of substrate derivatives incorporating substitution at N(4) and C(2), di‐ and spirocyclic substitution at C(5)‐ and C(6)‐position, as well as benzannulation (>35 examples in total). The DKR process is amenable to scale‐up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N‐C=O•••isothiouronium interaction identified as key to producing ester products in highly enantioenriched form.

  DOI：

  10.1002/anie.202402908
• 作为产物：
  描述：

  2-Benzylideneamino-m-cresol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-benzylamino-3-methylphenol
  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

• Enantioselective Copper-Catalyzed Formal [4 + 2] Cycloaddition of <i>o</i>-Aminophenol Derivatives with Propargylic Esters for Synthesis of Optically Active 3,4-Dihydro-2<i>H</i>-1,4-benzoxazines
  作者：Zhen-Ting Liu、Ya-Hui Wang、Fu-Lin Zhu、Xiang-Ping Hu

  DOI：10.1021/acs.orglett.6b00322

  日期：2016.3.4

  The first copper-catalyzed asymmetric formal [4 + 2] cycloaddition of o-aminophenol derivatives with propargylic esters as the bis-electrophilic C2 synthons for the stereoselective construction of chiral 2,3,4-trisubstituted 2H-1,4-benzoxazines bearing an exocyclic double bond has been developed. By using a structurally modified chiral ketimine P,N,N-ligand, a wide range of optically active 2H-1,4-benzoxazines

  首次铜催化邻氨基苯酚衍生物与炔丙酸酯作为双亲电子C2合成子的不对称[4 + 2]环加成，用于立体选择性地构建手性2,3,4-三取代的2 H -1,4-苯并恶嗪轴承已经开发了环外双键。通过使用结构改性的手性酮亚胺P，N，N-配体，可以高收率和极好的对映选择性（高达97％ee）制备各种光学活性的2 H -1,4-苯并恶嗪。
• 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，