N-benzyl-N-(5-bromo-2-hydroxybenzyl)methylamine

• 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-benzyl-N-(5-bromo-2-hydroxybenzyl)methylamine
• 英文别名: 2-((benzyl(methyl)amino)methyl)-4-bromophenol；2-{[benzyl(methyl)amino]methyl}-4-bromophenol；2-[[benzyl(methyl)amino]methyl]-4-bromophenol
• 化学式: C₁₅H₁₆BrNO
• 分子量: 306.202
• InChiKey: FWJKXZZKTXXLBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基苄胺 在 sodium percarbonate 、 碘 、 叔丁醇 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 26.0h， 生成 N-benzyl-N-(5-bromo-2-hydroxybenzyl)methylamine
  参考文献：
  名称：

  碘催化酚类水性 C-H 氨基甲基化

  摘要：

  已经开发了一种无过渡金属的策略，该策略涉及碘 - 过碳酸钠催化以实现水性介质中酚类的邻氨基甲基化。该方法可有效拓宽广泛的酚类化合物，耐受敏感的官能团，实现10个含酚结构的功能分子的后期功能化。

  DOI：

  10.1039/d2cc05746h

文献信息

• GO–Cu₇S₄ catalyzed <i>ortho</i>-aminomethylation of phenol derivatives with <i>N</i>,<i>N</i>-dimethylbenzylamines: site-selective oxidative CDC
  作者：Sonu Gupta、Nisha Chandna、Pooja Dubey、Ajai K. Singh、Nidhi Jain

  DOI：10.1039/c8cc03396j

  日期：——

  supported on graphene oxide (GO) have been synthesized for the first time from Cu2S, and used as highly efficient heterogeneous catalysts for oxidative ortho-selective C–H aminomethylation of phenols with N,N-dimethylbenzylamines. The NPs (30–80 nm) have been characterized by HRTEM, SEM-EDX, PXRD, FTIR, Raman, ICP-AES and XPS analyses. The NP catalyzed sp2–sp3 cross dehydrogenative coupling (CDC) features

  首次由Cu 2 S合成了负载在氧化石墨烯（GO）上的硫化铜铜纳米颗粒（Cu 7 S 4），并用作高效的非均相催化剂，用于酚与N，N的氧化邻位选择性C–H氨基甲基化-二甲基苄胺。NP（30–80 nm）已通过HRTEM，SEM-EDX，PXRD，FTIR，拉曼，ICP-AES和XPS分析进行了表征。NP催化的sp 2 –sp 3 交叉脱氢偶联（CDC）具有广泛的底物范围，优异的官能团耐受性，高收率，使用廉价且可重复使用的铜催化剂，温和的条件以及无需对底物进行预功能化。
• Ruthenium-Catalyzed Aminomethylation and Methylation of Phenol Derivatives Utilizing Methanol as the C₁Source
  作者：Seoksun Kim、Soon Hyeok Hong

  DOI：10.1002/adsc.201601117

  日期：2017.3.6

  involving ortho‐aminomethylation of phenol was developed via ruthenium‐catalyzed dehydrogenation of methanol, an environmentally benign C1 building block, without the use of reactive reagents. The reaction was successfully applied to a range of substrates. When naphthol was employed instead of phenol, only methylation was observed. On the basis of various mechanistic studies, we propose that formamide barely

  在不使用反应试剂的情况下，通过钌催化的甲醇的脱氢反应开发了一种涉及酚的邻氨基甲基化的反应，甲醇是一种对环境无害的C 1结构单元。该反应成功地应用于多种底物。当使用萘酚代替苯酚时，仅观察到甲基化。在各种机理研究的基础上，我们提出甲酰胺几乎不参与反应，这主要是通过亚胺阳离子中间体发生的。苯酚和萘酚的反应性差异归因于萘甲酸酯作为共轭碱的较强碱性，这是由于其芳香性较低。两种反应都提出了合理的反应途径。
• Nickel Catalyzed Ipso-hydroxylation and Subsequent Cross Dehydrogenative Coupling of Arylboronic Acids with Tertiary Amines: A Facile Access to α-phenolated Tertiary Amines
  作者：Promod Kumar、Anup Kumar Sharma、Rahul Singh、Tirumaleswararao Guntreddi、Krishna Nand Singh

  DOI：10.1002/adsc.201701625

  日期：2018.5.2

  been developed for the α‐functionalization of tertiary amines via sequential oxidative hydoxylation and cross‐dehydrogenative coupling (CDC) of arylboronic acids with tertiary amines to afford α‐phenolated tertiary amines. The results demonstrate an easy arylation of C(sp3)−H bond in the presence of an inexpensive and readily available nickel metal salt.

  通过芳基硼酸与叔胺的顺序氧化羟基化和交叉脱氢偶联（CDC），开发了一种简单，新颖的方法，用于叔胺的α-官能化，从而制得α-酚化叔胺。结果表明，在存在廉价且易于获得的镍金属盐的情况下，C（sp 3）-H键易于芳基化。
• Model Compounds Study on the Network Structure of Polybenzoxazines
  作者：Ho-Dong Kim、Hatsuo Ishida

  DOI：10.1021/ma030108+

  日期：2003.11.1

  The FT-IR and H-1 NMR spectra of model dimers, having different molecular sizes and pK(a), are investigated in order to understand the differences in the hydrogen-bonded network structures of polybenzoxazines. The correlation between the -(OHN)-N-... intramolecular hydrogen-bonding interaction and benzoxazine functional groups in the asymmetric dimers is investigated by H-1 NMR spectra. While the FT-IR spectra of the model dimers indicate that the nature of hydrogen bonding is closely related to the basicity of the amine constituent, the spectra of the corresponding polymers suggest the existence of different hydrogen-bonding interactions. The existence of phenolic linkage formation and the stability of the Mannich base structure during polymerization are investigated by a dimerization reaction. It is demonstrated that benzoxazines based upon extremely bulky amines do not develop desirable properties due to the extensive degradation process.