4-isopropylamino-2-phenyl-2-oxazoline | 203444-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-isopropylamino-2-phenyl-2-oxazoline
• 英文别名: 2-phenyl-N-propan-2-yl-4,5-dihydro-1,3-oxazol-4-amine
• CAS: 203444-40-0
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: UBJAQACFFHPDLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-isopropylamino-2-phenyl-2-oxazoline 在 盐酸 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 N-[3-isopropyl-2-(4-nitro-phenylimino)-oxazolidin-4-yl]-benzamide
  参考文献：
  名称：

  Direct conversion of 4-amino-2-phenyl-2-oxazolines into either 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides

  摘要：

  A novel heterocycle-heterocycle inter-conversion is reported. It enables direct and efficient syntheses of either polysubstituted 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides by a one-pot treatment of 4-amino-2-phenyl-2-oxazolines with arylisocyanates or arylisothiocyanates, respectively, followed by addition of hydrochloric acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00783-4
• 作为产物：
  描述：

  N-2,2-dichlorovinylbenzamide 在 四丁基高氯酸铵 、 sodium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-isopropylamino-2-phenyl-2-oxazoline
  参考文献：
  名称：

  A new synthetic route to 2-oxazolines. The electrochemical reduction of N-(2,2-dichloroethyl)amides as a key step

  摘要：

  A convenient new method for the synthesis of 2-oxazolines has been established involving the preparation of N-(2,2-dichloroethyl)amides followed by electrochemical reductive cyclizations. It has been applied successfully in preparing previously unknown 4-alkylamino-2-phenyl-2-oxazolines in fair to good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10730-4

文献信息

• The reaction of 4-amino-2-oxazolines with isocyanates and isothiocyanates. Synthesis and X-ray structures of polysubstituted 2-imidazolidinones, 1,3-oxazolidines and 1,3-thiazolidines
  作者：Antonio Guirado、Raquel Andreu、Bruno Martiz、Delia Bautista、Carmen Ramírez de Arellano、Peter G. Jones

  DOI：10.1016/j.tet.2006.04.058

  日期：2006.6

  However, the reactions with non-sulfonylated isocyanates or isothiocyanates were slower, leading to the expected ureido and thioureido derivatives 5, which were easily and efficiently transformed to either polysubstituted 2-imino-1,3-oxazolidine or 2-imino-1,3-thiazolidine hydrochlorides 7, respectively, by treatment with hydrochloric acid. The possible reasons for this disparity in chemical behaviour are

  4-烷基氨基-2-苯基-2-恶唑啉1与异氰酸酯和异硫氰酸酯的反应提供了空前有效的区域选择性杂环-杂环转化。化合物1与异氰酸甲苯酯快速反应，以几乎定量的产率直接产生3-烷基-4-苯甲酰胺基-1-甲苯磺酰基-2-咪唑啉酮4。相应的脲基中间体2不是可分离的物质。然而，与非磺酰化异氰酸酯或异硫氰酸酯的反应较慢，从而导致预期的脲基和硫脲基衍生物5，它们易于有效地转化为多取代的2-亚氨基-1,3-恶唑烷或2-亚氨基-1,3。 -噻唑烷盐酸盐7分别用盐酸处理。讨论了这种化学行为差异的可能原因。4-苯甲酰胺基-3-甲基-1-甲基-1-甲苯基-2-咪唑啉酮4b，4- [1-异丙基-3-（4-硝基苯基）脲基] -2-苯基-2-恶唑啉5e，（的X射线晶体结构已经确定了Z）-3-苄基-4-苯甲酰胺基-2-苯基亚氨基-1,3-恶唑烷盐酸盐7a和（Z）-3-苄基-4-苯甲酰胺基-2-苯基亚氨基-1,3-噻唑烷盐酸盐7b。
• Direct conversion of 4-amino-2-oxazolines into 2-imidazolidinones
  作者：Antonio Guirado、Raquel Andreu、Jesús Gálvez

  DOI：10.1016/s0040-4039(99)01682-2

  日期：1999.11

  A convenient new method for the synthesis of polysubstituted 2-imidazolidinones has been established involving the reaction of 4-alkylamino-2-aryl-2-oxazolines with arylsulfonyl isocyanates. It has been applied successfully in preparing previously unknown 3-alkyl-4-aroylamino-1-arylsulfonyl-2-imidazolidinones in high yields.

  已经建立了一种方便的合成多取代的2-咪唑啉酮的新方法，该方法涉及4-烷基氨基-2-芳基-2-恶唑啉与芳基磺酰基异氰酸酯的反应。它已成功地用于高产率地制备以前未知的3-烷基-4-芳酰基氨基-1-芳基磺酰基-2-咪唑啉酮。
• Electrochemical generation of 4-amino-2-aryl-2-oxazolines
  作者：Antonio Guirado、Raquel Andreu、Jesús Gálvez、Peter G Jones

  DOI：10.1016/s0040-4020(02)01288-7

  日期：2002.12

  A convenient method for the synthesis of the title compounds has been established. Chloralbenzamides were efficiently converted to N-(1-amino-2,2-dichloroethyl)benzamides which were directly transformed to 4-amino-2-aryl-2-oxazolines in fair to good yields by electrochemical reduction in an aprotic medium under constant cathodic potential. The molecular structure of the electrolysis products has been corroborated by X-ray crystallographic analysis of 4-(1-benzyl-3-phenylureido)-2-phenyl-2-oxazoline. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A new synthetic route to 2-oxazolines. The electrochemical reduction of N-(2,2-dichloroethyl)amides as a key step
  作者：Antonio Guirado、Raquel Andreu、Jesús Gálvez

  DOI：10.1016/s0040-4039(97)10730-4

  日期：1998.2

  A convenient new method for the synthesis of 2-oxazolines has been established involving the preparation of N-(2,2-dichloroethyl)amides followed by electrochemical reductive cyclizations. It has been applied successfully in preparing previously unknown 4-alkylamino-2-phenyl-2-oxazolines in fair to good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Direct conversion of 4-amino-2-phenyl-2-oxazolines into either 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides
  作者：Antonio Guirado、Raquel Andreu、Jesús Gálvez

  DOI：10.1016/s0040-4039(03)00783-4

  日期：2003.5

  A novel heterocycle-heterocycle inter-conversion is reported. It enables direct and efficient syntheses of either polysubstituted 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides by a one-pot treatment of 4-amino-2-phenyl-2-oxazolines with arylisocyanates or arylisothiocyanates, respectively, followed by addition of hydrochloric acid. (C) 2003 Elsevier Science Ltd. All rights reserved.