2-((dimethylamino)methyl)-6-fluorophenol

• 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-((dimethylamino)methyl)-6-fluorophenol
• 英文别名: 2-[(Dimethylamino)methyl]-6-fluorophenol
• 化学式: C₉H₁₂FNO
• 分子量: 169.199
• InChiKey: FQIAKKHPPYSTMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((dimethylamino)methyl)-6-fluorophenol 、 丙二腈 以 水 、 乙腈 为溶剂， 反应 0.5h， 以36%的产率得到2-amino-3-cyano-8-fluoro-4H-chromene
  参考文献：
  名称：

  从光化学生成的邻醌甲基丙二酸酯和丙二腈方便地合成2氨基4H色烯

  摘要：

  2-氨基-4- ħ -chromenes通过的反应在中等至良好的产率合成ö -quinone甲基化物的光化学产生从ø（二甲氨基甲基）酚与丙二腈- 。该方法适用于其他方法难以获得的氟化二苯甲基的合成。此外，在叔胺碱存在下，邻-（羟甲基）苯酚可用于反应。

  DOI：

  10.1002/jhet.1964
• 作为产物：
  描述：

  2-氟苯酚 、 n,n-二甲基亚甲基碘化胺 在 三乙胺 、 magnesium chloride 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-((dimethylamino)methyl)-6-fluorophenol
  参考文献：
  名称：

  Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines

  摘要：

  Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.064

文献信息

• Oxidative ortho-amino-methylation of phenols via C–H and C–C bond cleavage
  作者：Wenbo Sun、Huacan Lin、Wenyu Zhou、Zigang Li

  DOI：10.1039/c3ra46373g

  日期：——

  Initiated by CCl3Br, phenols undergo efficient ortho-selective oxidative cross dehydrogenative coupling (CDC) with trimethylamine. When tetramethylethylenediamine (TMEDA) is used instead of trimethylamine, oxidative carbon–carbon activation coupling (CAC) could occur to give the same salicylamines together with CDC by-products. These reactions are accelerated by a gold salt.

  在 CCl3Br 的作用下，苯酚与三甲胺发生高效的正选择性氧化交叉脱氢偶联（CDC）。当使用四甲基乙二胺（TMEDA）代替三甲胺时，可发生氧化碳-碳活化偶联（CAC），生成相同的水杨胺和 CDC 副产物。金盐可加速这些反应。
• Convenient Synthesis of 2-Amino-4<i>H</i>-chromenes from Photochemically Generated<i>o</i>-Quinone Methides and Malononitrile
  作者：Makoto Fujiwara、Masanori Sakamoto、Kimihiro Komeyama、Hiroto Yoshida、Ken Takaki

  DOI：10.1002/jhet.1964

  日期：2015.1

  2‐Amino‐4H‐chromenes were synthesized in moderate to good yields by the reaction of o‐quinone methides photochemically generated from o‐(dimethylaminomethyl)phenols with malononitrile. This method was applicable to the synthesis of fluorinated chromenes that were difficult to obtain by other methods. In addition, o‐(hydroxymethyl)phenols could be used for the reaction in the presence of tertiary amine bases.

  2-氨基-4- ħ -chromenes通过的反应在中等至良好的产率合成ö -quinone甲基化物的光化学产生从ø（二甲氨基甲基）酚与丙二腈- 。该方法适用于其他方法难以获得的氟化二苯甲基的合成。此外，在叔胺碱存在下，邻-（羟甲基）苯酚可用于反应。
• Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines
  作者：Hany F. Anwar、Lars Skattebøl、Trond Vidar Hansen

  DOI：10.1016/j.tet.2007.07.064

  日期：2007.10

  Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines. (c) 2007 Elsevier Ltd. All rights reserved.