4-氨基丁-2-酮盐酸盐 | 21419-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氨基丁-2-酮盐酸盐
• 英文名称: 3-Amino-2-butanone hydrochloride
• 英文别名: (+/-)-2-amino-3-butanone hydrochloride；2-Amino-3-butanone hydrochloride；3-aminobutan-2-one hydrochloride；3-aminobutanone hydrochloride；3-amino-butan-2-one; hydrochloride；3-aminobutan-2-one;hydrochloride
• CAS: 21419-24-9
• 化学式: C₄H₉NO*ClH
• mdl: MFCD16619121
• 分子量: 123.582
• InChiKey: PJUJCERLTHVZRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338
• 危险品运输编号：
  1759
• 危险性描述：
  H318
• 包装等级：
  III
• 储存条件：
  储存条件：2-8°C，需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  4-氨基丁-2-酮盐酸盐 在 air 、 sodium acetate 作用下， 以 甲醇 为溶剂， 以73%的产率得到川芎嗪
  参考文献：
  名称：

  Electrolytic Oxidation of Ketones in Ammoniacal Methanol in the Presence of Catalytic Amounts of KI

  摘要：

  The indirect electrooxidation of ketones in ammoniacal methanol using iodide ion as a mediator afforded 2,2-dialkyl-2,5-dihydro-1H-imidazoles 3 via an oxidative cyclocoupling of ketimine intermediates formed from ketones and ammonia. The treatment of 3 with dilute HCl gave alpha-amino ketone hydrochlorides 4 and the parent ketones in good yields. A similar electrooxidation of 3 resulted in the formation of the corresponding W-imidazoles 6, which were hydrolyzed to alpha-diketones and the parent ketones. The same products 6 could also conveniently be obtained by chemical oxidation of 3 with aqueous NaOCl.

  DOI：

  10.1021/jo00126a027
• 作为产物：
  描述：

  2-Ethyl-2,4,5-trimethyl-2,5-dihydro-1H-imidazole 在 盐酸 作用下， 以70%的产率得到4-氨基丁-2-酮盐酸盐
  参考文献：
  名称：

  Electrolytic Oxidation of Ketones in Ammoniacal Methanol in the Presence of Catalytic Amounts of KI

  摘要：

  The indirect electrooxidation of ketones in ammoniacal methanol using iodide ion as a mediator afforded 2,2-dialkyl-2,5-dihydro-1H-imidazoles 3 via an oxidative cyclocoupling of ketimine intermediates formed from ketones and ammonia. The treatment of 3 with dilute HCl gave alpha-amino ketone hydrochlorides 4 and the parent ketones in good yields. A similar electrooxidation of 3 resulted in the formation of the corresponding W-imidazoles 6, which were hydrolyzed to alpha-diketones and the parent ketones. The same products 6 could also conveniently be obtained by chemical oxidation of 3 with aqueous NaOCl.

  DOI：

  10.1021/jo00126a027

文献信息

• Studies on Isothiazoles. III. A Novel Ring Closure to Isothiazoles by the Reaction of α-Amino Ketones with Thionyl Chloride or Sulfur Monochloride
  作者：Takayuki Naito、Susumu Nakagawa、Jun Okumura、Kiyoshi Takahashi、Ken-ichi Kasai

  DOI：10.1246/bcsj.41.959

  日期：1968.4

  New compounds, 4-hydroxyisothiazoles, have been prepared by the reaction of α-amino ketones with thionyl chloride or sulfur monochloride, which is a novel procedure for cyclization to an isothiazole ring. Polar solvents, especially dimethylformamide (DMF), were preferable for this cyclization. The reaction hardly proceeded in a nonpolar solvent such as benzene, but was accelerated by an addition of

  通过α-氨基酮与亚硫酰氯或一氯化硫反应制备了新化合物4-羟基异噻唑，这是一种环化成异噻唑环的新方法。极性溶剂，尤其是二甲基甲酰胺 (DMF)，对于这种环化反应是优选的。该反应在苯等非极性溶剂中几乎不进行，但通过加入少量 DMF 可加速反应。
• [EN] 6-CYCLOALKYL-1, 5-DIHYDRO-PYRAZOLO [3, 4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A INHIBITORS<br/>[FR] DÉRIVÉS DE 6-CYCLOALKYL-1,5-DIHYDRO-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE PDE9A
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012020022A1

  公开（公告）日：2012-02-16

  The invention relates to novel 6-Cycloalkyl-pyrazolopyrimidinones according to formula (I) wherein R1 is a 5 or 6 membered aromatic heteroaryl-group, R2 is an optional substituent, D is optionally substituted cyclopentyl, cyclohexyl, tetrahydrofuranyl, tetrahydropyranyl or 2-, 3- or 4-pyridyl, m= 1 or 2 and n is 0, 1 or 2. The new compounds are for use as the active entity of medicaments or for the manufacture of medicaments respectively, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. Such conditions may for example be associated with Alzheimers disease, schizophrenia and other diseases. The new compounds are also for example for the manufacture of medicaments and/or for use in the treatment of these diseases, in particular for cognitive impairment associated with such disease. The compounds of the invention show PDE9 inhibiting properties.

  该发明涉及根据式(I)的新型6-环烷基吡唑吡嘧啶酮，其中R1是5或6成员芳香杂环基团，R2是可选取代基，D是可选取代的环戊基、环己基、四氢呋喃基、四氢吡喃基或2-、3-或4-吡啶基，m=1或2，n为0、1或2。这些新化合物可用作药物的活性成分或用于制造药物，特别是用于治疗涉及感知、注意力、学习或记忆缺陷的疾病的药物。这些疾病可能与阿尔茨海默病、精神分裂症和其他疾病有关。这些新化合物还可用于制造药物和/或用于治疗这些疾病，特别是与此类疾病相关的认知障碍。该发明的化合物显示PDE9抑制特性。
• 6-Cycloalkyl-pyrazolopyrimidinones for the Treatment of CNS Disorders
  申请人：Heine Niklas

  公开号：US20120202829A1

  公开（公告）日：2012-08-09

  The invention relates to novel 6-Cycloalkyl-pyrazolopyrimidinones according to formula (I). wherein R 1 is a 5 or 6 membered aromatic heteroaryl-group, R 2 is an optional substituent, D is optionally substituted cyclopentyl, cyclohexyl, tetrahydrofuranyl, tetrahydropyranyl or 2-, 3- or 4-pyridyl, m=1 or 2 and n is 0, 1 or 2. The new compounds are for use as the active entity of medicaments or for the manufacture of medicaments respectively, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. Such conditions may for example be associated with Alzheimer's disease, schizophrenia and other diseases. The new compounds are also for example for the manufacture of medicaments and/or for use in the treatment of these diseases, in particular for cognitive impairment associated with such disease. The compounds of the invention show PDE9 inhibiting properties.

  该发明涉及根据式(I)的新型6-环烷基吡唑吡嘧啶酮。 其中R1是5或6成员芳香杂环基团，R2是可选取代基，D是可选取代的环戊基、环己基、四氢呋喃基、四氢吡喃基或2-、3-或4-吡啶基，m=1或2，n为0、1或2。 这些新化合物可用作药物的活性成分或用于制造药物，特别是用于治疗涉及感知、注意力、学习或记忆缺陷的疾病的药物。这些疾病可能与阿尔茨海默病、精神分裂症和其他疾病有关。这些新化合物还可用于制造药物和/或用于治疗这些疾病，特别是与这些疾病相关的认知障碍。该发明的化合物显示PDE9抑制特性。
• Concise Synthesis of 1<i>H</i>-Pyrazin-2-ones and 2-Aminopyrazines
  作者：Peter Meier、Isabelle Adam、David Orain

  DOI：10.1055/s-2004-830866

  日期：——

  Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.

  本文描述了1H-吡嗪-2-酮和2-氨基吡嗪的便捷合成方法。通过将Boc保护的氨基酸与α-氨基酮或氨基醇耦合并随后进行氧化反应，可以得到1H-吡嗪-2-酮。将其转化为相应的三氟甲基磺酸吡嗪并进行一级或二级胺的取代反应，则可得到2-氨基吡嗪。由于这些合成方法利用了易于获得的起始原料（例如氨基酸、氨基醇和胺），因此可以在少数高效步骤中获得各种所需的结构。
• Synthesis of new 1H-imidazoles via reactions of 3(,5)-(di)chloro-2H-1,4-(benz)oxazin-2-ones with α-aminoketones
  作者：Bart P. Medaer、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(99)00087-3

  日期：1999.3

  react with α-aminoketones to yield bi- and tricyclic imidazo-fused intermediates via an intramolecular cyclisation reaction. Reaction of these lactone intermediates with various nucleophiles generates new substituted 1H-imidazoles useful for pharmacological screening. Reactions of compounds 1 with β-amino-alcohols followed by treatment with SOCl2 provides 2,3-dihydro-8H-imidazo[2,1-c]-1,4-oxazin-8-ones

  3,5-二氯-2 H -1,4-恶嗪-2-酮1和3-氯-2 H -1,4-苯并恶嗪-2-酮2与α-氨基酮反应生成双环和三环咪唑-通过分子内环化反应稠合的中间体。这些内酯中间体与各种亲核试剂的反应产生了可用于药理学筛选的新的取代的1 H-咪唑。化合物1与β-氨基醇的反应，然后用SOCl 2处理，得到2,3-二氢-8 H-咪唑并[ 2,1 - c ] -1,4-恶嗪-8-酮，但内酯裂解导致一些未知的分解产物的形成。