2-二甲氨基甲基-5-甲基-苯酚 | 56501-37-2

• 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: 2-二甲氨基甲基-5-甲基-苯酚
• 英文名称: 2-Dimethylaminomethyl-5-methyl-phenol
• 英文别名: 2-((Dimethylamino)methyl)-5-methylphenol；2-[(dimethylamino)methyl]-5-methylphenol
• CAS: 56501-37-2
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: FTOYQDIBORAUQK-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46.5 °C
• 沸点：
  58-61 °C(Press: 0.04 Torr)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-二甲氨基甲基-5-甲基-苯酚 在 1,4-二氧六环 、 copper oxide-chromium oxide 作用下， 160.0 ℃ 、12.75 MPa 条件下， 生成 2,5-二甲基苯酚
  参考文献：
  名称：

  151.合成与甾醇有关的物质的实验。第XLVI部分。4-酮-1：1-二烷基哌啶鎓盐的合成用途

  摘要：

  DOI：

  10.1039/jr9490000708
• 作为产物：
  描述：

  (3R,6R)-5-[1-Dimethylamino-meth-(E)-ylidene]-tricyclo[4.1.0.0^1,3]heptan-4-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以0.124 g的产率得到2-二甲氨基甲基-5-甲基-苯酚
  参考文献：
  名称：

  Ring Expansion and Contraction of a Two-Carbon Bridged Spiropentane

  摘要：

  The reactions of tricyclo[4.1.0.0(1,3)]heptan-4-one (5) and two related systems with diazomethane and m-CPBA were examined in order to determine the relative reactivity and migratory aptitudes for the three compounds. The reactions of 5 with diazomethane and m-CPBA yielded new derivatives of the tricyclo[5.1.0.0(1,3)]octane ring system that showed that migration of cyclopropylcarbinyl is favored over cyclopropyl migration in this system. Photolysis of 5-diazotricyclo[4.1.0.0(1,3)]heptan-4-one (23) in methanol and dimethylamine did not lead to ring contraction to the tricyclo[3.1.0.0(1,3)]hexane ring system, but an interesting product was derived from an unusual rearrangement process in the photolysis in dimethylamine. Matrix photolysis of 23 at 15 K gave a decrease in the diazo band at 2085 cm(-1) and the appearance of a new band at 2117 cm(-1), which is a normal position expected for a small-ring ketene such as cyclopropylketene. Thus, matrix photolysis appears to have yielded a derivative of the previously unknown tricyclo[3.1.0.0(1,3)]hexane ring system. The lithium enolate of 5 was characterized by NMR spectroscopy at -80 degrees C and was found to rearrange to m-cresol at -65 degrees C. The geometries of the bridged spiropentanes of this work were optimized at the MP2(frozen core)/6-31G* level of theory, and group equivalent values were derived in order to calculate the heats of formation for these compounds using the calculated energies.

  DOI：

  10.1021/jo970980e

文献信息

• 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。
• Selective Synthesis of Phenolic Mannich Bases under Solid-Liquid Phase Transfer Conditions
  作者：Andrea Pochini、Giuseppe Puglia、Rocco Ungaro

  DOI：10.1055/s-1983-30560

  日期：——
• Synthesis and Characterization of O,N-Chelated Vanadium(IV) Oxo Phenolate Complexes:  Electronic Effect of Meta and Para Substituents on the Vanadium Center
  作者：Henk Hagen、Antonio Barbon、Ernst E. van Faassen、Bert T. G. Lutz、Jaap Boersma、Anthony L. Spek、Gerard van Koten

  DOI：10.1021/ic9901564

  日期：1999.9.1

  A series of O,N-chelated vanadium(IV) oxo bis(phenolate) complexes (1a-i) have been prepared from [VOCl2(THF)(2)] and several ortho-amino-functionalized phenols in the presence of a base. The intermediates in the synthesis of these compounds are mono(phenolato)vanadate complexes, as was shown by the reaction of [VOCl2(THF)(2)] with 1 equiv of HOC6H2(CH2NMe2)(2)-2,6-Me-4 in the absence of base. This yielded [VOCl2(OC6H2(CH2NMe2)2-Me-4-(CH2NHMe2)-6)] (2), in which the second amine function acts as an internal base, assisting in binding the formed equivalent of HCl. Complex 2 exists in the solid state as the dichlorovanadate(IV) species with the protonated amine function forming a three-centered intramolecular hydrogen bridge in which both a chloride atom and the oxygen atom of the phenolate ligand participate. EPR, UV-vis, and cyclic voltammetry analysis of the complexes with meta or para substituents (1a-g) on the aryloxy ring showed the hyperfine coupling constant, the HOMO-LUMO transition, and the oxidation potential, respectively, to be linearly related to the Hammett sigma constants of the substituents on the monoanionic aryloxy ring. The oxidation potential shows a large dependence (dE(ox)/d sigma = 170 mV (per phenoxy ligand)) on the Hammett constant. Crystal data: 1a, orthorombic, Pbca, a = 9.4321(7) Angstrom, b = 14.1919(14) Angstrom, c = 26.5484(14) Angstrom, V = 3553.8(5), Angstrom(3), Z = 8; 2, monoclinic, C2/c, a = 17.9977(15) Angstrom, b = 15.7445(9) Angstrom, c = 14.4986(6) Angstrom, beta = 113.206(5)degrees, V = 3776.0(4) Angstrom(3), Z = 4.
• POCHINI, A.;PUGLIA, G.;UNGARO, K., SYNTHESIS, BRD, 1983, N 11, 906-907
  作者：POCHINI, A.、PUGLIA, G.、UNGARO, K.

  DOI：——

  日期：——
• [EN] COMPOSITION<br/>[FR] COMPOSITION
  申请人：ASS OCTEL

  公开号：WO2005087901A2

  公开（公告）日：2005-09-22

  The present invention provides a fuel additive composition comprising (i) at least one primary antiknock component selected from (a) iron or an iron compound; (b) lead or a lead compound; (c) manganese or manganese compound; and (d) a metal selected from rare earth metals, lithium, nickel, and thallium or a compound comprising a metal selected from rare earth metals, lithium, nickel, and thallium; (ii) at least one secondary antiknock component selected from (a) oxyhydrocarbyl compounds; and (b) nitrohydrocarbyl compounds; (iii) at least one of (a) a sulphur passivating agent, (b) a material capable of preventing and/or inhibiting valve seat recession of an internal combustion engine.