N,N’,N’’-triacetylguanidine | 107572-98-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N’,N’’-triacetylguanidine
• 英文别名: N,N',N''-triacetylguanidine；N,N',N''-triacetyl-guanidine；N,N',N''-Triacetyl-guanidin；N-(N,N'-diacetylcarbamimidoyl)acetamide
• CAS: 107572-98-5
• 化学式: C₇H₁₁N₃O₃
• 分子量: 185.183
• InChiKey: KZEWNKKIZZJOMW-UHFFFAOYSA-N

物化性质

• 熔点：
  104-108 °C
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N’,N’’-triacetylguanidine 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 0.33h， 以57%的产率得到1,1,1-tris(acetamido)methane
  参考文献：
  名称：

  通过选择性硼氢化物还原的Orthoamides Ñ，Ñ '，Ñ “-triacyl-和Ñ，Ñ '，Ñ ” -三（烷氧基羰基）-guanidines

  摘要：

  Ñ，Ñ '，Ñ “-Triacylguanidines和Ñ，Ñ '，Ñ ” -三（烷氧基羰基）胍的制备和在四氢呋喃和乙酸的混合物中，用硼氢化盐还原，得到三酰基中的产率和三（烷氧基羰基）orthoamides 40–85％。但是，类似的减少Ñ，Ñ '，Ñ “ -三（吨丁氧基羰基）胍没有给orthoamide但缩醛胺二（吨丁基）亚甲基二。

  DOI：

  10.1016/j.tetlet.2018.12.060
• 作为产物：
  描述：

  碳酸胍 、 乙酸酐 反应 1.5h， 以51%的产率得到N,N’,N’’-triacetylguanidine
  参考文献：
  名称：

  通过选择性硼氢化物还原的Orthoamides Ñ，Ñ '，Ñ “-triacyl-和Ñ，Ñ '，Ñ ” -三（烷氧基羰基）-guanidines

  摘要：

  Ñ，Ñ '，Ñ “-Triacylguanidines和Ñ，Ñ '，Ñ ” -三（烷氧基羰基）胍的制备和在四氢呋喃和乙酸的混合物中，用硼氢化盐还原，得到三酰基中的产率和三（烷氧基羰基）orthoamides 40–85％。但是，类似的减少Ñ，Ñ '，Ñ “ -三（吨丁氧基羰基）胍没有给orthoamide但缩醛胺二（吨丁基）亚甲基二。

  DOI：

  10.1016/j.tetlet.2018.12.060

文献信息

• GUANIDINE COMPOUNDS: III. THE PREPARATION OF TRIACETYLGUANIDINE AND ITS TRANSFORMATION WITH ALCOHOL
  作者：R. Greenhalgh、R. A. B. Bannard

  DOI：10.1139/v59-265

  日期：1959.11.1

  Triacetylguanidine has been prepared and shown to undergo stepwise deacetylation in the presence of alcohol to guanidine acetate. Diacetylguanidine has been shown to have a m.p. 176–177° and not 166° as previously reported.

  三乙酰基胍已经被制备出来，并且在醇的存在下逐步脱乙酰基，形成乙酸胍。二乙酰基胍的熔点为176-177℃，而不是先前报道的166℃。
• Organometallic complexes of platinum-group metals incorporating substituted guanidine dianion (triazatrimethylenemethane) ligands
  作者：Maarten B. Dinger、William Henderson、Brian K. Nicholson

  DOI：10.1016/s0022-328x(97)00654-2

  日期：1998.4

  Reactions of the platinum-group metal halide complexes [PtCl2(COD)] (COD = 1,5-cyclo-octadiene), [Cp*RhCl2(PPh3)] (Cp* = eta(5)-C5Me5), [Cp*IrCl2(PPh3)], [(p-cymene)RuCl2(PPh3)] and [(p-cymene)OsCl2(PPh3)] with symmetrically trisubstituted (acetyl or phenyl) guanidines, mediated by silver(I) oxide, give complexes formally containing the triazatrimethylenemethane ligand. A full X-ray crystal structure determination is reported for the N,N',N "-triphenylguanidine dianion complex [PtNPhC(=NPh)NPh}(COD)] 4a which shows the presence of a planar Pt-NR-C(=NR)-NR four-membered platinacycle. At room temperature (r.t.), the H-1- and C-13H-1}-NMR spectra of 4a yield a single set of COD CH and CH2 resonances. At 240 K however, two sets of resonances are observed, interpreted in terms of fluxionality of the C=N-Ph moiety. Attempted synthesis of the analogous platinum triacetylguanidine complex yields the new ureylene complex [PtNAcC(=O)NAc}(COD)], via a hydrolysis reaction. Starting with the osmium compound, both the guanidine complex [(p-cymene)OsNAcC(=NAc)NAc}(PPh3)] 9 and the ureylene complex [(p-cymene)OsNAcC(=O)NAc}(PPh3)] 10 were formed; similar results were obtained for the iridium system. (C) 1998 Elsevier Science S.A. All rights reserved.
• Orthoamides by selective borohydride reduction of N,N′,N″-triacyl- and N,N′,N″-tri(alkoxycarbonyl)-guanidines
  作者：Matthew C. Davis、Thomas J. Groshens

  DOI：10.1016/j.tetlet.2018.12.060

  日期：2019.1

  N,N′,N″-Triacylguanidines and N,N′,N″-tri(alkoxycarbonyl)guanidines were prepared and reduced with borohydride salts in a mixture of tetrahydrofuran and acetic acid to give triacyl and tri(alkoxycarbonyl) orthoamides in yields of 40–85%. However, similar reduction of N,N′,N″-tri(t-butoxycarbonyl)guanidine did not give orthoamide but the aminal di(t-butyl) methylenedicarbamate.

  Ñ，Ñ '，Ñ “-Triacylguanidines和Ñ，Ñ '，Ñ ” -三（烷氧基羰基）胍的制备和在四氢呋喃和乙酸的混合物中，用硼氢化盐还原，得到三酰基中的产率和三（烷氧基羰基）orthoamides 40–85％。但是，类似的减少Ñ，Ñ '，Ñ “ -三（吨丁氧基羰基）胍没有给orthoamide但缩醛胺二（吨丁基）亚甲基二。