5-甲基-2-(吗啉-4-基甲基)苯酚 | 6967-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-甲基-2-(吗啉-4-基甲基)苯酚
• 英文名称: 5-methyl-2-(morpholinomethyl)phenol
• 英文别名: 5-methyl-2-(N-morpholinyl)methylphenol；N-(2-hydroxy-4-methylbenzyl)morpholine；5-Methyl-2-(morpholin-4-ylmethyl)phenol
• CAS: 6967-79-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: NQDVYJAUXHJMKM-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C
• 沸点：
  158-160 °C(Press: 4.999 Torr)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-甲基-2-(吗啉-4-基甲基)苯酚 、 三甲基镓 以 苯 为溶剂， 以89%的产率得到dimethylgallium-[4-methyl-2-(N-morpholinomethyl)-1-phenoxide]
  参考文献：
  名称：

  Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes: crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]

  摘要：

  The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (la), 4-methyl-2-(n-morpholinomethyl)-1-phenol (Ib), 4-chloro-2-(n-morpholinomethyl)-1-phenol (Ic), 4-nitro-2-(n-morpholinomethyl)-1-phenol(ld), and 1-(n-morpholinomethyl)-naphthol (le). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face pi-pi stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00148-5
• 作为产物：
  描述：

  吗啉 、 2-羟基-4-甲基苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成 5-甲基-2-(吗啉-4-基甲基)苯酚
  参考文献：
  名称：

  Cu(II)-催化苯酚的邻位选择性氨基甲基化

  摘要：

  已经开发出一种 Cu(II) 催化的游离酚与三氟硼酸盐的邻位选择性官能化，以在温和条件下提供 Csp2-Csp3 偶联产物。发现苯酚和氨基甲基三氟硼酸钾底物上的各种官能团是相容的，以中等至极好的收率提供相应的产品。提出了一种涉及六元过渡态的单电子转移自由基偶联机制，以合理化反应中的高水平邻位选择性。该协议提供了对邻氨基甲基取代酚、非天然氨基酸和其他生物活性小分子的直接访问。

  DOI：

  10.1021/jacs.7b06785

文献信息

• The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines
  作者：Juan Liu、Gaoqing Yuan

  DOI：10.1016/j.tetlet.2017.02.081

  日期：2017.4

  A modified Mannich reaction has been developed for the synthesis of Mannich bases and benzoxazines via the oxidative hydroxylation of arylboronic acids and subsequent coupling with paraformaldehyde and amines in one pot. This modified Mannich reaction is easily carried out to afford the target products in good to excellent yields and tolerates a variety of functional groups.

  已开发出一种改良的曼尼希反应，用于通过芳基硼酸的氧化羟基化反应，随后在一个罐中与多聚甲醛和胺偶联来合成曼尼希碱和苯并恶嗪。容易进行这种修饰的曼尼希反应，以高至优异的产率提供目标产物，并能耐受多种官能团。
• Synthesis of N-[2-hydroxy-4(5)-methyl- and -5-(methylcyclohexyl)benzyl]morpholines as antioxidants for transformer oils
  作者：Ch. K. Rasulov、A. G. Azizov、F. A. Nabiev、S. T. Rustamov、A. S. Askerova

  DOI：10.1134/s107042721012013x

  日期：2010.12

  Aminomethylation of m- and p-cresols and of p-(1-methylcyclohexyl)phenol with formaldehyde and morpholine was studied. The products obtained were tested as antioxidant additives to T-1500 transformer oil.

  的氨基甲基化米和- p -cresols和p - （1-甲基环己基）与甲醛和苯酚吗啉进行了研究。测试所得产物作为T-1500变压器油的抗氧化剂添加剂。
• Cu(II)-Catalyzed <i>ortho</i>-Selective Aminomethylation of Phenols
  作者：Jin-Ling Dai、Nan-Qi Shao、Jin Zhang、Run-Ping Jia、Dong-Hui Wang

  DOI：10.1021/jacs.7b06785

  日期：2017.9.13

  A Cu(II)-catalyzed ortho-selective functionalization of free phenols with trifluoroborates to afford Csp2-Csp3 coupling products under mild conditions has been developed. A variety of functional groups on the phenol and the potassium aminomethyltrifluoroborate substrates were found compatible, furnishing the corresponding products in moderate to excellent yields. A single-electron transfer radical

  已经开发出一种 Cu(II) 催化的游离酚与三氟硼酸盐的邻位选择性官能化，以在温和条件下提供 Csp2-Csp3 偶联产物。发现苯酚和氨基甲基三氟硼酸钾底物上的各种官能团是相容的，以中等至极好的收率提供相应的产品。提出了一种涉及六元过渡态的单电子转移自由基偶联机制，以合理化反应中的高水平邻位选择性。该协议提供了对邻氨基甲基取代酚、非天然氨基酸和其他生物活性小分子的直接访问。
• Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes: crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]
  作者：Jing-zhi Tian、Jin-qi Zhang、Xi Shen、Hui-xian Zou

  DOI：10.1016/s0022-328x(99)00148-5

  日期：1999.7

  The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (la), 4-methyl-2-(n-morpholinomethyl)-1-phenol (Ib), 4-chloro-2-(n-morpholinomethyl)-1-phenol (Ic), 4-nitro-2-(n-morpholinomethyl)-1-phenol(ld), and 1-(n-morpholinomethyl)-naphthol (le). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face pi-pi stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported. (C) 1999 Elsevier Science S.A. All rights reserved.