苯酚,2-[[(4-甲氧苯基)亚甲基]氨基]-4-甲基- | 19430-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 苯酚,2-[[(4-甲氧苯基)亚甲基]氨基]-4-甲基-
• 英文名称: 2-(p-Methoxy-benzylidenamino)-p-kresol
• 英文别名: 2-{(E)-[(4-Methoxyphenyl)methylidene]amino}-4-methylphenol；2-[(4-methoxyphenyl)methylideneamino]-4-methylphenol
• CAS: 19430-23-0
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: UUQSEHNXWNQLRX-UHFFFAOYSA-N

物化性质

• 沸点：
  435.5±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯酚,2-[[(4-甲氧苯基)亚甲基]氨基]-4-甲基- 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-methyl-2-(4’-methoxybenzylamino)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
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 邻氨基对甲苯酚 以 乙醇 为溶剂， 反应 3.0h， 生成 苯酚,2-[[(4-甲氧苯基)亚甲基]氨基]-4-甲基-
  参考文献：
  名称：

  手性恶唑硼烷鎓离子催化的与醛亚胺的对映选择性Strecker和烯丙基化反应。

  摘要：

  已经开发了使用氰化三丁基锡和烯丙基三丁基锡烷的手性恶唑硼烷鎓离子（COBI）催化的醛亚胺的对映选择性亲核加成反应。以高产率（高达98％）和高至极好的对映选择性（高达99％ee）合成了各种α-氨基腈和均烯丙基胺。提供了用于COBI和醛亚胺复合物的合理机理模型来解释这些对映选择性反应。

  DOI：

  10.1021/acs.orglett.9b02280

文献信息

• Reactions of α,<i>N</i>-Diarylnitrones with<i>O</i>-Methyl Diphenylphosphinothioate and Oxidations of<i>N</i>-Alkylidene-2-hydroxyanilines with Silver Oxide. Preparation of Benzoxazoles
  作者：Masaaki Yoshifuji、Rihei Nagase、Naoki Inamoto

  DOI：10.1246/bcsj.55.873

  日期：1982.3

  Reactions of α,N-diarylnitrones in the presence of O-methyl diphenylphosphinothioate at 150 °C gave 2-arylbenzoxazoles (3) in fairly good yields. Oxidation of N-alkylidene-2-hydroxyanilines with silver oxide afforded 2-alkenyl-, 2-alkyl-, or 2-arylbenzoxazoles (7 and 3) in good yields under mild reaction conditions (at room temperature). A plausible mechanism for formation of 3 and 7 has been discussed

  α,N-二芳基硝酮在 O-甲基二苯基硫代膦酸酯存在下于 150 °C 反应，以相当好的收率得到 2-芳基苯并恶唑 (3)。用氧化银氧化 N-亚烷基-2-羟基苯胺，在温和的反应条件下（室温）以良好的产率得到 2-烯基-、2-烷基-或 2-芳基苯并恶唑（7 和 3）。已经简要讨论了形成 3 和 7 的合理机制。
• A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction
  作者：Louisa Chouguiat、Raouf Boulcina、Bertrand Carboni、Albert Demonceau、Abdelmadjid Debache

  DOI：10.1016/j.tetlet.2014.07.093

  日期：2014.9
• Nano-tube TiO2 as a new catalyst for eco-friendly synthesis of imines in sunlight
  作者：Mona Hosseini-Sarvari

  DOI：10.1016/j.cclet.2010.11.017

  日期：2011.5

  Nanomaterials are considered as suitable heterogeneous catalysts for many organic reactions. Herein nano-tube TiO2 has been reported as a heterogeneous catalyst, for synthesis of imines in sunlight at room temperature under solvent-free conditions. The condensation of less electrophilic carbonyl compounds with poorly nucleophilic amines was afforded imines in excellent yields. (c) 2010 Mona Hosseini-Sarvari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.