3-(N,N-dimethylaminomethyl)benzene-1,2-diol | 94483-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(N,N-dimethylaminomethyl)benzene-1,2-diol
• 英文别名: 3-(dimethylaminomethyl)benzene-1,2-diol；3-(N,N-dimethylaminomethyl)catechol；3-Dimethylaminomethyl-brenzkatechin；1,2-Benzenediol, 3-((dimethylamino)methyl)-；3-[(dimethylamino)methyl]benzene-1,2-diol
• CAS: 94483-71-3
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: FVIHLQHUULUVEB-UHFFFAOYSA-N

物化性质

• 沸点：
  270.0±25.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(N,N-dimethylaminomethyl)benzene-1,2-diol 在 硅酸四乙酯 作用下， 以 乙醇 为溶剂， 以48%的产率得到[3-(N,N-dimethylaminomethyl)catecholato(2-)]bis[3-(N,N-dimethylammmoniomethyl)catecholato(2-)]silicate(IV)
  参考文献：
  名称：

  摘要：

  This paper reports the synthesis and characterization of a number of novel silicon(IV) complexes with a range of mono-Mannich bases of benzene-1,2-diol. Mannich bases of general structure 3-(dialkylaminomethyl) benzene-1,2-diol form zwitterionic 6-coordinate tris complexes with silicon(IV), eliminating the need for an external counter ion. These complexes exhibit marked differences in their ability to partition between an aqueous and organic phase compared with the analogous tris(benzene-1,2-diol) silicon(IV) complex. Mannich bases of diamines and benzene-1, 2-diol will also complex to silicon; however, they result in more complicated polymeric structures.

  DOI：

  10.1071/ch01064
• 作为产物：
  描述：

  2-(dimethylaminomethyl)-6-methoxyphenol 在 氢碘酸 作用下， 生成 3-(N,N-dimethylaminomethyl)benzene-1,2-diol
  参考文献：
  名称：

  Reactions of Isopropyl Methylphosphonofluoridate with Substituted Phenols. II

  摘要：

  DOI：

  10.1021/ja01076a043

文献信息

• Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers
  作者：Jiang Duan、Wenhai Wu、Zengfeng Wei、Dedou Zhu、Haiyang Tu、Aidong Zhang

  DOI：10.1039/c7gc03323k

  日期：——

  facile synthesis of 4-/3-substituted catechols using the Mannich reaction of catechol with formaldehyde and secondary amines. The reaction proceeds smoothly in water without any catalyst. Separation of the desired products is important for the success of this methodology, and was achieved by a pH-controlled solvent extraction and recrystallization process. The synthesized functional catechols not only

  近年来，含邻苯二酚的聚合物因其贻贝启发的多功能粘合功能而备受关注。我们在此报告了使用邻苯二酚与甲醛和仲胺的曼尼希反应，可轻松合成4- / 3-取代的邻苯二酚。该反应在没有任何催化剂的情况下在水中顺利进行。所需产物的分离对于该方法的成功很重要，这是通过pH控制的溶剂萃取和重结晶过程实现的。合成的官能邻苯二酚不仅表现出多巴胺样的氧化交联，而且具有可用于合成含邻苯二酚的聚合物的官能团。作为概念验证应用，有两种功能性邻苯二酚，
• 邻苯二酚衍生物及其仿生聚合物的合成与应 用
  申请人：华中师范大学

  公开号：CN108178730B

  公开（公告）日：2021-06-15

  本发明公开了一类邻苯二酚衍生物及仿生聚合物的合成方法与应用，属于高分子生物材料和功能材料领域。本发明以廉价易得的邻苯二酚、甲醛、二级胺为原料，通过Mannich反应得到4‑位胺甲基取代的邻苯二酚衍生物和3‑位胺甲基取代的邻苯二酚衍生物。仿生聚合物为含有邻苯二酚聚氨酯仿生聚合物或含有邻苯二酚聚丙烯酸酯仿生聚合物，聚合物单体经过加聚或自由基聚合制得含邻苯二酚结构的仿生聚合物。本发明得到的邻苯二酚衍生物，可用于含邻苯二酚结构单元仿生聚合物的合成；由邻苯二酚衍生物合成得到的仿生聚合物，具有优异的形成涂层的能力、抗蛋白吸附能力、以及形成水凝胶的能力，在医用粘接剂、医用水凝胶、涂层材料等方面具有应用价值。
• ——
  作者：Marcus J. Caulfield、Tiziana Russo、David H. Solomon

  DOI：10.1071/ch00079

  日期：——

  The synthesis of a number of novel dibenzene-1,2-diol Mannich bases can be achieved in good yields by the condensation of 2-methoxyphenol, formaldehyde and secondary diamines. The newly developed synthetic method utilizes 2-methoxyphenol instead of benzene-1,2-diol providing a useful tool for greater control over reaction products.
• Inhibition and inactivation of presynaptic cholinergic markers using redox-reactive choline analogs
  作者：Phenil J. Patel、William S. Messer、Richard A. Hudson

  DOI：10.1021/jm00065a012

  日期：1993.6

  Inhibition and inactivation of two presynaptic cholinergic ''markers'', choline acetyltransferase and high affinity choline transporter, has been investigated using inhibitors designed with a redox-reactive catechol tethered to a quaternary ammonium group. Two quaternary ammonium alkyl-substituted catechols, 3[(trimethylammonio)methyl]catechol (TMC, 1) and NN-dimethylepinephrine (catecholine, 2) were shown to bind weakly and noncompetitively to bovine choline acetyltransferase yet inactivated the enzyme in a time course consistent with the involvement of early intermediates in the spontaneous oxidation of these catechols. Both agents also inhibited high-affinity choline uptake. The time course of TMC and catecholine spontaneous oxidation-dependent inactivation of high affinity choline uptake sites was slower than, if it occurred at all, the spontaneous degradation of measurable choline transport in synaptosomes. When compared with inhibition of uptake of other neurotransmitters, it was shown that catecholine demonstrated more selectivity than TMC toward inhibition of choline transport. K(m) (muM) and V(max) (pmol/min per mg of protein) were measured for high affinity transport of choline, dopamine, and serotonin and were observed to be K(m) = 2.04 +/- 0.31, V(max) = 22 +/- 1; K(m) = 1.4, V(max) = 53; and K(m) = 0.15, V(max) = 23, respectively, in good agreement with published literature values. K(i)'s (mM) for catecholine and TMC, calculated from experimentally determined IC50's, were for catecholine 0.13 +/- 0.06, 0.53 +/- 0.09, and 0.39 +/- 0.10, and for TMC 0.06 +/- 0.03, 0.09 +/- 0.03, and 0.09 +/- 0.08, for choline, dopamine, and serotonin transport, respectively. In vivo studies using catecholine suggest that this compound impairs learning ability associated with long-term memory. Thus, catecholine represents a lead compound in a potential series of redox-reactive choline analogs, which may become useful irreversible antagonists of the critical cholinergic macromolecular targets underlying cholinergic hypofunction in disorders such as Alzheimer's disease.
• US4710521A
  申请人：——

  公开号：US4710521A

  公开（公告）日：1987-12-01