2-amino-5-(3-aminopropyl)-1H-imidazolin-4-one | 129693-81-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-5-(3-aminopropyl)-1H-imidazolin-4-one
• 英文别名: 2-amino-4-(3-aminopropyl)-1,4-dihydroimidazol-5-one
• CAS: 129693-81-8
• 化学式: C₆H₁₂N₄O
• 分子量: 156.187
• InChiKey: RIGZCOADFLIZTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 2-amino-5-(3-aminopropyl)-1H-imidazolin-4-one 以 甲醇 为溶剂， 反应 168.0h， 以80%的产率得到N-(2-Oxo-piperidin-3-yl)-guanidine; compound with acetic acid
  参考文献：
  名称：

  Unusually Large ¹³C NMR Chemical Shift Differences between Neutral and Protonated Glycocyamidines. New Insights on Previously Reported Chemical Shift Assignments and Chemical Properties

  摘要：

  Unusually large C-13 chemical shift differences are observed between neutral and protonated glycocyamidine (2-aminoimidazolinone) derivatives. Upon-protonation, the guanidine (N-C=N) and carbonyl (C=O) carbons undergo an upfield shift of approximately 12 and 17 ppm, respectively; relative to the neutral species. For neutral glycocyamidine derivatives, the C-13 chemical shifts for the carbonyl carbon reside above 190 ppm. In the protonated form, the carbonyl resonances are in the mid to lower 170s. These values are indicative of the protonation state of the glycocyamidine moiety. The present study serves as a useful reference in assisting the characterization of future glycocyamidine-based natural products and derivatives.

  DOI：

  10.1021/jo972295d
• 作为产物：
  描述：

  4-(3-aminopropyl)-1H-imidazol-2-ylamine dihydrochloride 在 N-氯代丁二酰亚胺 作用下， 以 xylene 为溶剂， 反应 4.0h， 生成 2-amino-5-(3-aminopropyl)-1H-imidazolin-4-one
  参考文献：
  名称：

  Synthesis of Marine Sponge Alkaloids Oroidin, Clathrodin, and Dispacamides. Preparation and Transformation of 2-Amino-4,5-dialkoxy-4,5-dihydroimidazolines from 2-Aminoimidazoles

  摘要：

  The preparation and transformation of 2-amino-4,5-dialkoxy-4,5-dihydroimidazolines A from 2-aminoimidazoles (AIs) is described. The oxidation of 2-aminoimidazole 8 with NCS in methanol affords cyclic guanidine adduct 9 which, upon heating, affords vinylogous AI derivative 3 and 8-aminoimidazolinone (glycocyamidine) 13. Olefin 3 comprises the core structure found in the oroidin alkaloids. Furthermore, oxidation of 8 with B-2 and DMSO affords directly alpha,beta-unsaturated imidazolinone 14 which is the key structural unit comprising the dispacamides (2). A highly facile and practical synthesis of the C11N5 marine sponge alkaloids oroidin (la), clathrodin (1c), and dispacamides (2) is outlined.

  DOI：

  10.1021/jo9718298

文献信息

• Abderhalden; Sickel, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1929, vol. 180, p. 80
  作者：Abderhalden、Sickel

  DOI：——

  日期：——
• Synthesis of Marine Sponge Alkaloids Oroidin, Clathrodin, and Dispacamides. Preparation and Transformation of 2-Amino-4,5-dialkoxy-4,5-dihydroimidazolines from 2-Aminoimidazoles
  作者：Anne Olofson、Kenichi Yakushijin、David A. Horne

  DOI：10.1021/jo9718298

  日期：1998.2.1

  The preparation and transformation of 2-amino-4,5-dialkoxy-4,5-dihydroimidazolines A from 2-aminoimidazoles (AIs) is described. The oxidation of 2-aminoimidazole 8 with NCS in methanol affords cyclic guanidine adduct 9 which, upon heating, affords vinylogous AI derivative 3 and 8-aminoimidazolinone (glycocyamidine) 13. Olefin 3 comprises the core structure found in the oroidin alkaloids. Furthermore, oxidation of 8 with B-2 and DMSO affords directly alpha,beta-unsaturated imidazolinone 14 which is the key structural unit comprising the dispacamides (2). A highly facile and practical synthesis of the C11N5 marine sponge alkaloids oroidin (la), clathrodin (1c), and dispacamides (2) is outlined.
• Unusually Large ¹³C NMR Chemical Shift Differences between Neutral and Protonated Glycocyamidines. New Insights on Previously Reported Chemical Shift Assignments and Chemical Properties
  作者：Anne Olofson、Kenichi Yakushijin、David A. Horne

  DOI：10.1021/jo972295d

  日期：1998.8.1

  Unusually large C-13 chemical shift differences are observed between neutral and protonated glycocyamidine (2-aminoimidazolinone) derivatives. Upon-protonation, the guanidine (N-C=N) and carbonyl (C=O) carbons undergo an upfield shift of approximately 12 and 17 ppm, respectively; relative to the neutral species. For neutral glycocyamidine derivatives, the C-13 chemical shifts for the carbonyl carbon reside above 190 ppm. In the protonated form, the carbonyl resonances are in the mid to lower 170s. These values are indicative of the protonation state of the glycocyamidine moiety. The present study serves as a useful reference in assisting the characterization of future glycocyamidine-based natural products and derivatives.