2-氨基-5-(4-苯基-1-哌嗪甲基)-2-恶唑啉 | 91595-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-氨基-5-(4-苯基-1-哌嗪甲基)-2-恶唑啉
• 英文名称: 4,5-dihydro-5--2-oxazolamine
• 英文别名: 5-<(1-phenyl-4-piperazinyl)methyl>-2-amino-2-oxazoline；5-[(1-phenyl-4-piperazinyl)methyl]-2-amino-2-oxazoline；5-(1-phenyl-4-piperazinyl)methyl-2-amino-2-oxazoline；5-(1-phenyl-4-piperazino)methyl 2-amino-2-oxazoline；5-(1-phenyl-4-piperazino)methyl-2-amino-2-oxazoline；4,5-Dihydro-5-(4-phenyl-1-piperazinylmethyl)-2-oxazolamine；5-[(4-phenylpiperazin-1-yl)methyl]-4,5-dihydro-1,3-oxazol-2-amine
• CAS: 91595-86-7；145585-42-8
• 化学式: C₁₄H₂₀N₄O
• 分子量: 260.339
• InChiKey: XSZLHACSCSAKOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-5-(4-苯基-1-哌嗪甲基)-2-恶唑啉 以 丙酮 为溶剂， 反应 24.5h， 生成 2-(1-phenyl-4-piperazinyl)methyl-7-methyl-2,3-dihydro-5H-oxazolo[3,2-a]pyrimidin-5-one
  参考文献：
  名称：

  从相应的2-氨基-2-恶唑啉开始的2-取代-2,3-二氢-5（7）H-恶唑并[3,2 - a ]嘧啶-5-酮和7-酮的简便方法

  摘要：

  异构体2-取代的7（5）-甲基-2,3-二氢-5（7）H-恶唑并[3,2- a ]嘧啶-5-酮3a-b和7-酮2a-b，7a由5-取代的2-氨基-2-恶唑啉1a-b与双亲电子试剂通过环缩合反应合成。在沸腾的乙醇中，1a-b与炔属酯的反应生成2a-b，7a与少量（E）-2 - N-（2-乙氧基羰基乙烯）-5-取代的-2-亚氨基恶唑啉5a的混合物-b。在1a-b和双烯酮之间的环环化反应产生了2-取代的7-羟基-7-甲基-2,3,6,7-四氢-5 H-恶唑[3,2-a ]嘧啶-5-酮4a-b，可以容易地脱水以提供2-取代的-7-甲基-2,3-二氢-5 H-恶唑[3,2 - a ]嘧啶-5-酮3a- b。

  DOI：

  10.1002/jhet.5570380403
• 作为产物：
  描述：

  3-[4-苯基哌嗪基]-2-羟丙基氯 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 39.0h， 生成 2-氨基-5-(4-苯基-1-哌嗪甲基)-2-恶唑啉
  参考文献：
  名称：

  Synthesis and antidepressant activity of 5-(1-aryl-4-piperazino)methyl-2-amino-2-oxazolines

  摘要：

  The synthesis of 20 5-(1-aryl-4-piperazino)methyl-2-amino-2-oxazolines is described. Antidepressant activity was observed in mice using classical screening tests. Structure-activity relationships were studied and correlated with the nature of the aromatic substituent. Preliminary lipophilic and electronic properties of one lead compound (COR 3224) have been described.

  DOI：

  10.1016/0223-5234(92)90177-3

文献信息

• 2-Amino-2-oxazolines, III: Synthesis, Structure, and Preliminary Pharmacological Evaluation of Cycloaddition Compounds with Unsaturated Carboxylic Esters
  作者：Isabelle Forfar、Christian Jarry、Jean-Michel Leger、Alain Carpy

  DOI：10.1002/ardp.19903231105

  日期：——

  The reaction of 5‐substituted 2‐amino‐2‐oxazolines with unsaturated carboxylic esters yielded 2,3,5,6‐tetrahydro‐ and 2,3‐dihydro‐7H‐oxazolo[3,2‐a]pyrimidin‐7‐ones. The structure of these compounds was established by IR‐ and NMR‐spectra and by X‐ray crystallography. They were tested for anti‐arrhythmic and hypocholesterolemic activities.

  5-取代的2-氨基-2-恶唑啉与不饱和羧酸酯反应生成2,3,5,6-四氢-和2,3-二氢-7H-恶唑并[3,2-a]嘧啶-7- . 这些化合物的结构是通过 IR 和 NMR 光谱以及 X 射线晶体学确定的。测试了它们的抗心律失常和低胆固醇活性。
• New investigation of the reaction of 2-amino-2-oxazolines with isocyanates and isothiocyanates. Evidence of a transposition during the second step
  作者：Jean-Jacques Bosc、Christian Jarry、Jamal Ouhabi、Michel Laguerre、Alain Carpy

  DOI：10.1139/v96-150

  日期：1996.7.1

  The reaction of some 2-amino-2-oxazolines with isocyanates and arylisothiocyanates yields 3-monosubstituted or 2,3-disubstituted 2-iminooxazolidines depending on the experimental conditions and on the nature of the electrophile reactants. The structures of a mono- and a disubstituted derivative were established by X-ray analysis. The chemical behaviour of the compounds was investigated by molecular and quantum mechanics calculations. An intramolecular transposition during the second step of the reaction was found. Key words: 2-amino-2-oxazolines, iso(thio)cyanates, transposition. X-ray structure, MOPAC calculations.

  一些2-氨基-2-噁唑啉与异氰酸酯和芳基异硫氰酸酯的反应取决于实验条件和亲电试剂的性质，生成3-单取代或2,3-二取代的2-亚氨基噁唑啉。通过X射线分析确定了单取代和二取代衍生物的结构。通过分子和量子力学计算研究了化合物的化学行为。在反应的第二步中发现了一种分子内转位。关键词：2-氨基-2-噁唑啉，异（硫）氰酸酯，转位。X射线结构，MOPAC计算。
• 2-Amino-2-oxazolines, IV: Kurzmitteilung: Reactions with Bromo Esters, Synthesis of Some 3-Carboxyalkyl-2-imino-oxazolidines
  作者：Christian Jarry、Catherine Misiaszek

  DOI：10.1002/ardp.19903231113

  日期：——

  2‐Amino‐2‐oxazoline, 4. Mitt.: Reaktionen mit Bromestern, Synthese einiger 3‐Carboxyalkyl‐2‐imino‐oxazolidine

  2 - 氨基 - 2 - 恶唑啉，第 4 部分：与溴酯的反应，一些 3 - 羧基烷基 - 2 - 亚氨基 - 恶唑烷的合成
• 2-Amino-2-oxazolines, II: Reactivity of the Nitrogens. Crystal Structures of Twoendo/exo N-Substituted Compounds
  作者：Jean-Jacques Bosc、Isabelle Forfar、Christian Jarry、Jamal Ouhabi、Jean-Michel Leger、Alain Carpy

  DOI：10.1002/ardp.19903230902

  日期：——

  amino/imino equilibrium. In the 2‐amino‐2‐oxazoline form the endo nitrogen is more reactive than the exo one. In the imino‐2‐oxazolidine form, the contrary occurs. Depending on the experimental conditions, substitutive reactions take place either on the endo or on the exo nitrogen. The crystal structures of two endo/exo N‐substituted compounds were determined by X‐ray crystallography.

  五元杂环的脒基诱导互变异构的氨基/亚氨基平衡。在 2-氨基-2-恶唑啉形式中，内氮比外氮更具反应性。在亚氨基-2-恶唑烷形式中，情况正好相反。根据实验条件，取代反应发生在内部或外部氮上。通过 X 射线晶体学确定了两种内/外 N 取代化合物的晶体结构。
• Reaction of 5-Substituted 2-Amino-2-oxazolines with Ethoxycarbonyl Isothiocyanate
  作者：Christian Jarry、Isabelle Forfar、Jacqueline Thomas、Jean Michel Leger、Michel Laguerre

  DOI：10.3987/com-93-6381

  日期：——

  The reaction of 2-amino-2-oxazolines with ethoxycarbonyl isothiocyanate was found to give only 2,3,6,7-tetrahydro-4H-oxazolo[3,2-a]-1,3,5-triazin-2-one-4-thiones, the structure of which was confirmed by X-ray crystallographic analysis. The direction of attack seems to be related to the more potent nucleophilic character of the endo nitrogen atom in 2-amino-2-oxazolines. In basic conditions the oxazoline ring can be easily hydrolyzed leading to 1-substituted 1,3,5-triazin-2,4-dione-6-thione.