4-[(二甲基氨基)甲]-2,6-二异丙基苯醇 | 4918-95-0

• 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: 4-[(二甲基氨基)甲]-2,6-二异丙基苯醇
• 中文别名: 2,5-二氢-3-甲基-1-苯基-1-氧化磷
• 英文名称: NSC 68328
• 英文别名: 4-Dimethylaminomethyl-2,6-diisopropyl-phenol；(4-hydroxy-3,5-diisopropylbenzyl)-dimethylamine；N.N-Dimethyl-N-(3.5-diisopropyl-4-hydroxybenzyl)amin；4-((Dimethylamino)methyl)-2,6-diisopropylphenol；4-[(dimethylamino)methyl]-2,6-di(propan-2-yl)phenol
• CAS: 4918-95-0
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: DEYFSRVIHDNQHT-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86°C
• 沸点：
  300.6±37.0 °C(Predicted)
• 密度：
  0.962±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  4-[(二甲基氨基)甲]-2,6-二异丙基苯醇 在 sodium methylate 作用下， 以 乙二醇 为溶剂， 生成 5-(3,5-diisopropyl-4-methoxy-benzyl)-6-methylsulfanyl-pyrimidine-2,4-diamine
  参考文献：
  名称：

  2,4-二氨基-5-苄基嘧啶类作为抗菌剂。4.来自酚类曼尼希中间体的6-取代的甲氧苄啶衍生物。在合成甲氧苄啶和3,5-二烷基苄基类似物上的应用。

  摘要：

  通过2,4-二氨基-6-取代的嘧啶与2,6-二甲氧基-4-[（N，N-二甲基氨基）甲基]苯酚的反应可轻松完成多种6-取代的甲氧苄啶类似物的制备较低反应性的2,6-二烷基-4-[（N，N-二甲基氨基）甲基]酚与2,4-二氨基-6-（烷硫基）嘧啶成功反应生成5-（取代的苄基）嘧啶。当在嘧啶环中存在非反应性6-取代基时，产物的酚基以高产率烷基化。用阮内镍很容易除去6-（烷硫基）基团。因此从其6-（甲硫基）对应物以高收率获得甲氧苄啶。6-取代的甲氧苄啶类似物作为大肠杆菌二氢叶酸还原酶的抑制剂和抗菌剂均具有较低的活性。

  DOI：

  10.1021/jm00179a012
• 作为产物：
  描述：

  聚合甲醛 、 丙泊酚 、 二甲胺 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 12.0h， 以30%的产率得到4-[(二甲基氨基)甲]-2,6-二异丙基苯醇
  参考文献：
  名称：

  Propofol Analogues. Synthesis, Relationships between Structure and Affinity at GABA_A Receptor in Rat Brain, and Differential Electrophysiological Profile at Recombinant Human GABA_A Receptors

  摘要：

  A number of propofol (2,6-diisopropylphenol) congeners and derivatives were synthesized and their in vitro capability to affect GABA(A) receptors determined by the inhibition of the specific [S-35]-tert-butylbicyclophosphorothionate ([S-35]TBPS) binding to rat whole brain membranes. Introduction of halogen (Cl, Br, and I) and benzoyl substituents in the para position of the phenyl group resulted in ligands with higher potency at inhibiting [S-35]TBPS binding. A quantitative structure-affinity relationship (QSAR) study demonstrated that affinity is enhanced by increases in lipophilicity of the ligand whereas affinity is adversely affected by increases in size of the substituent para to the phenolic hydroxyl group. Consistent with the displacement of [S-35]TBPS and with the activation of GABA(A) receptors, we demonstrate that ligands displaying high affinity (i.e., 2-4, and 8) are able to increase GABA-stimulated chloride currents in oocytes expressing human GABA(A) receptors and to directly activate chloride currents in an electrophysiological assay. Among them, compound 4 showed a rather peculiar profile in the electrophysiological examination with cloned alpha(1) beta(2) gamma(2) GABA(A) receptors. Indeed, compared to propofol, it displayed a much greater efficacy at potentiating GABA-elicited chloride currents, but a much lower efficacy at producing a direct activation of the chloride channel in the absence of GABA. This behavior may give to compound 4 pharmacological properties that are more similar to anxiolytic and anticonvulsant drugs than to those of general anesthetics.

  DOI：

  10.1021/jm970681h

文献信息

• 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogs
  作者：Barbara Roth、Justina Z. Strelitz、Barbara S. Rauckman

  DOI：10.1021/jm00178a007

  日期：1980.4

  A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and

  已经开发出一种新的5-（对羟基苄基）嘧啶的方法，该方法利用酚类曼尼希碱加上含有至少两个活化基团的嘧啶。取决于条件，产物可以在酚氧或嘧啶N-1原子上烷基化。该方法已被用来制备广谱抗菌剂甲氧苄啶，它是从2,4-二氨基嘧啶和2,6-二甲氧基苯酚开始的。
• Bis(4-hydroxy-3,5-dialkylbenzyl)cyano-carboxylic acid esters
  申请人：Ciba-Geigy Corporation

  公开号：US03950382A1

  公开（公告）日：1976-04-13

  The reaction of one mole of a Mannich base corresponding to the formula ##SPC1## And one mole of a Mannich base corresponding to the formula ##SPC2## Wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 are independently selected from alkyl groups having 1 to 6 carbon atoms and R is alkyl, preferably lower alkyl, with 1 mole of a carboxylic acid ester corresponding to the formula R.sub.3 CH.sub.2 COOR.sub.4 wherein R.sub.3 is --H, --CN or --COOR.sub.4 and R.sub.4 is an alkyl, thioether, oxyether or aralkyl group having up to 20 carbons in the presence of a catalytically effective amount of an alkaline catalyst is useful for preparing compounds corresponding to the formula ##SPC3## The compounds represented by the above formula are useful as stabilizers for synthetic resins, particularly polyolefins. Compounds of the above formula, when R.sub.3 is --CN are novel and may also be prepared by reacting 1 mole of ##SPC4## And 1 mole of ##SPC5## Wherein X is halogen with 1 mole of NCCH.sub.2 COOR.sub.4 in the presence of an alkali metal and an anhydrous inert organic solvent.

  将一个摩尔的Mannich碱反应，其化学式为##SPC1##，和一个摩尔的Mannich碱反应，其化学式为##SPC2##，其中R.sub.1，R.sub.2，R.sub.4和R.sub.5分别为1至6个碳原子的烷基，而R是烷基，优选为低烷基，与一个摩尔的羧酸酯反应，其化学式为R.sub.3 CH.sub.2 COOR.sub.4，其中R.sub.3为--H，--CN或--COOR.sub.4，而R.sub.4为具有多达20个碳的烷基，硫醚，氧醚或芳基烷基，在碱性催化剂的存在下是制备符合以下化学式的化合物的有用方法##SPC3##上述化学式所代表的化合物可用作合成树脂的稳定剂，特别是聚烯烃。当R.sub.3为--CN时，上述化学式的化合物是新颖的，并且也可以通过在碱金属和无水惰性有机溶剂的存在下，将1摩尔的##SPC4##和1摩尔的##SPC5##反应，其中X为卤素，与1摩尔的NCCH.sub.2 COOR.sub.4反应来制备。
• 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 3. C-Benzylation of aminopyridines with phenolic Mannich bases. Synthesis of 1- and 3-deaza analogs of trimethoprim
  作者：Barbara S. Rauckman、Barbara Roth

  DOI：10.1021/jm00178a008

  日期：1980.4

  -4-[(N,N-dimethylamino)methyl]phenols and by halogens (bromine and fluorine) produces 3-benzyl and 3-halo derivatives, plus a small amount of disubstitution at the 3,5 positions. Treatment of a 2,4-diamino-3-halopyridine with phenolic Mannich bases gives 5- and N-benzylation. 2,4-Diamino-3-bromo-5-(4-hydroxy-3,5-dimethoxybenzyl)pyridine was methylated on the phenolic group in good yield and dehalogenated

  2,4-二氨基-4-[（N，N-二甲基氨基）甲基]苯酚和卤素（溴和氟）的2,4-二氨基吡啶亲电取代产生3-苄基和3-卤代衍生物，以及少量衍生物在3,5职位上的混乱状况。用酚曼尼希碱处理2，4-二氨基-3-卤代吡啶得到5-和N-苄基化。2,4-二氨基-3-溴-5-（4-羟基-3,5-二甲氧基苄基）吡啶在酚基上甲基化，产率高，然后脱卤生成3-脱氮杂甲氧苄啶[2,4-二氨基-5-（ 3,4,5-三甲氧基苄基）吡啶]。该化合物作为大肠杆菌二氢叶酸还原酶抑制剂的活性比甲氧苄氨嘧啶低约300倍。2,6-二氨基吡啶很容易被酚曼尼希碱在3,5位以及氨基上二苄基化；使用四倍过量的吡啶以50％的产率提供了3-苄基化的2，6-二氨基吡啶。在10（-4）M时，它不能作为二氢叶酸还原酶的抑制剂。在此处报道的条件下，2-氨基吡啶和4-氨基吡啶不会产生C-苄基化产物。
• Substituted benzyl diketones and process therefor
  申请人：ETHYL CORPORATION

  公开号：EP0105772A2

  公开（公告）日：1984-04-18

  The present invention deals with substituted benzyl diketones and a process for their preparation. Novel 2-(3',5'-dihydrocarbyl-4'-hydroxybenzyl)-1,3-diketones are prepared by reacting an N,N-dihydrocarbyl 2,6-dihydrocarbyl-4-aminomethylphenol with a 1,3-diketone and an alkyl halide in the presence of an alkali or an alkaline earth metal hydride. The resulting substituted benzyl diketones are useful as antioxidants into polymers, latices, liquid hydrocarbon fuels and lubricating oils.

  本发明涉及取代苄基二酮及其制备工艺。 新型 2-(3',5'-二氢羰基-4'-羟基苄基)-1,3-二酮是在碱或碱土金属氢化物存在下，通过 N,N-二氢羰基 2,6-二氢羰基-4-氨基甲基苯酚与 1,3-二酮和烷基卤化物反应制备的。 由此产生的取代苄基二酮类化合物可用作聚合物、乳液、液态烃燃料和润滑油的抗氧化剂。
• Novel substituted benzylated malonic acid esters and process therefor
  申请人：ETHYL CORPORATION

  公开号：EP0103529A1

  公开（公告）日：1984-03-21

  The present invention deals with novel substituted benzylated malonic acid esters and a process for their preparation. Esters of 3,5-dihydrocarbyl-4-hydroxybenzyl-malonic acid are prepared by reacting an N,N-dihydrocarbyl-2,6-dihydrocarbyl-4-aminomethylphenol with an ester of a 1,3-dicarboxylic acid in the presence of an alkali or an alkaline earth metal hydride. The resulting substituted benzylated malonic acid esters are useful as antioxidants into polymers, latices, liquid hydrocarbon fuels and lubricating oils.

  本发明涉及新型取代苄基丙二酸酯及其制备工艺。 3,5-二氢羰基-4-羟基苄基丙二酸酯是在碱或碱土金属氢化物存在下，通过 N,N-二氢羰基-2,6-二氢羰基-4-氨基甲基苯酚与 1,3-二羧酸酯反应制备的。 生成的取代苄基丙二酸酯可用作聚合物、乳液、液态烃燃料和润滑油的抗氧化剂。