3,3-Dimethyl-2-hydroxymethylbutyl-1-amine | 15521-17-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,3-Dimethyl-2-hydroxymethylbutyl-1-amine
• 英文别名: 2-(hydroxymethyl)-3,3-dimethylbutylamine；2-Aminomethyl-3,3-dimethyl-butanol-1；2-(Aminomethyl)-3,3-dimethylbutan-1-ol
• CAS: 15521-17-2
• 化学式: C₇H₁₇NO
• mdl: MFCD19204020
• 分子量: 131.218
• InChiKey: BARCWXONXKELGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-Dimethyl-2-hydroxymethylbutyl-1-amine 在 劳森试剂 、 sodium hydroxide 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 xylene 为溶剂， 反应 8.0h， 生成 2-(4-Bromophenyl)-5-tert-butyl-4H-1,3-thiazine
  参考文献：
  名称：

  Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines

  摘要：

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.

  DOI：

  10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p
• 作为产物：
  描述：

  2-(carbethoxy)-3,3-dimethylbutyric acid 在 lithium aluminium tetrahydride 、 氯化亚砜 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 50.5h， 生成 3,3-Dimethyl-2-hydroxymethylbutyl-1-amine
  参考文献：
  名称：

  Conformations of saturated six-membered ring phosphorus heterocycles. cis- and trans-2-oxo- and -2-thio-2-(dimethylamino)-5-tert-butyl-1,3,2 .lambda.5-oxazaphosphorinanes: molecules related to cyclophosphamide

  摘要：

  DOI：

  10.1021/ja00387a039

文献信息

• Effect of nitrogen substituents on the relative energies of twist and chair-form conformations of 2-oxo-2-dimethylamino-5--butyl-1,3,2-oxazaphosphorinanes
  作者：S. Chandrasekaran、Wesley G. Bentrude

  DOI：10.1016/0040-4039(80)88090-7

  日期：1980.1

  Replacement of the phenyl substituent on nitrogen of the 1,3,2-oxaza ring of the title compounds changes the twist-chair equilibrium such that the chair conformation is populated rather than the twist form primarily occupied in the N-phenyl case. A possible rationale based on Me2N-phenyl interactions is proposed.

  标题化合物的1,3,2-氧杂氮杂环的氮上的苯基取代基的取代改变了扭曲-椅平衡，使得填充了椅构象，而不是主要存在于N-苯基情况下的扭曲形式。提出了基于Me 2 N-苯基相互作用的可能原理。
• Some new alkamino esters of quinuclidine-, piperidine- and pyridinecarboxylic acids
  作者：E. S. Nikitskaya、E. I. Levkoeva、V. S. Usovskaya、M. V. Rubtsov

  DOI：10.1007/bf00768577

  日期：1967.3

  Some new alkamino esters of quinuclidine-2-carboxylic, 1,6-dimethylpiperidine-2-carboxylic and 6-methylpyridine-2-carboxylic acid and their quaternary salts have been synthesized for pharmacological study. The methods of synthesis for some alkamino alcohols are described.

  一些新的奎宁环-2-羧酸、1,6-二甲基哌啶-2-羧酸和6-甲基吡啶-2-羧酸的烷氨基酯及其季盐已被合成用于药理学研究。描述了一些烷氨基醇的合成方法。
• Inhibitors of syk and JAK protein kinases
  申请人：Jia Zhaozhong

  公开号：US20100048567A1

  公开（公告）日：2010-02-25

  The present invention is directed to compounds of formula I-V and tautomers thereof or pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of syk kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition syk kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by syk kinase activity, such as undesired thrombosis and Non Hodgkin's Lymphoma.

  本发明涉及公式I-V的化合物及其互变异构体或药学上可接受的盐、酯和前药，其是syk激酶的抑制剂。本发明还涉及用于制备这种化合物的中间体，制备这种化合物的方法，包含这种化合物的制药组合物，抑制syk激酶活性的方法，抑制血小板聚集的方法，以及预防或治疗至少部分由syk激酶活性介导的多种疾病的方法，例如不良血栓和非何杰金淋巴瘤。
• INHIBITORS OF SYK AND JAK PROTEIN KINASES
  申请人：Jia Zhaozhong

  公开号：US20120101275A1

  公开（公告）日：2012-04-26

  The present invention is directed to compounds of formula I-V and tautomers thereof or pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of syk kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition syk kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by syk kinase activity, such as undesired thrombosis and Non Hodgkin's Lymphoma.

  本发明涉及公式I-V和其互变异构体或药学上可接受的盐、酯和前药的化合物，其为syk激酶的抑制剂。本发明还涉及用于制备这种化合物的中间体，制备这种化合物的方法，含有这种化合物的制药组合物，抑制syk激酶活性的方法，抑制血小板聚集的方法，以及预防或治疗至少部分由syk激酶活性介导的多种情况的方法，如非霍奇金淋巴瘤和不良血栓形成。
• BENZAMIDES AND NICOTINAMIDES AS SYK MODULATORS
  申请人：Jia Zhaozhong J.

  公开号：US20120142671A1

  公开（公告）日：2012-06-07

  The present invention is directed to compounds of formula I and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of Syk kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition Syk kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by Syk kinase activity, such as Non Hodgkin's Lymphoma.

  本发明涉及公式I的化合物及其药学上可接受的盐、酯和前药，这些化合物是Syk激酶的抑制剂。本发明还涉及用于制备这些化合物的中间体，制备这种化合物的方法，含有这种化合物的药物组合物，抑制Syk激酶活性的方法，抑制血小板聚集的方法，以及预防或治疗至少部分由Syk激酶活性介导的多种疾病，如非霍奇金淋巴瘤的方法。