N-(1H-benzimidazol-2-yl) propionimidic acid ethyl ester | 166320-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-(1H-benzimidazol-2-yl) propionimidic acid ethyl ester
• 英文别名: ethyl (1Z)-N-(1H-benzimidazol-2-yl)propanimidate
• CAS: 166320-41-8
• 化学式: C₁₂H₁₅N₃O
• 分子量: 217.271
• InChiKey: OVOGYMJUFAXHNJ-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(1H-benzimidazol-2-yl) propionimidic acid ethyl ester 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 47.0h， 生成 N-phenyl-N'-[1-(N,N,N',N'-tetramethylphosphamidoyl)-1H-benzimidazol-2-yl]-propionamidine
  参考文献：
  名称：

  SYNTHESIS AND REACTVITY OF N-[N-PHOSPHORAMIDO-1H-BENZIMIDAZOL-2-YL] IMIDATES

  摘要：

  N-(-1H-Benzimidazol-2-yl) imidates 1a-c react with chlorophosphoramide to give the N-[-1-N,N,N',N'-tetramethylphosphoramidoyl-1H-benzimidazol-2-yl]-imidates 2a-c or with dichlorophosphoramide to yield the bis[(N-1-benzimidazol-2-yl)-imidate]phosphoramide derivatives 3a-b. The reaction of compounds 2a-c toward primary amines is studied. The obtained amidine derivatives 4a-b were unambiguously characterized by different spectroscopic techniques (IR, H-1, C-13, and P-31 NMR, and in some cases MS).

  DOI：

  10.1080/10426500490485372
• 作为产物：
  描述：

  2-氨基苯并咪唑 、 原丙酸三乙酯 在 溶剂黄146 作用下， 反应 3.0h， 生成 N-(1H-benzimidazol-2-yl) propionimidic acid ethyl ester
  参考文献：
  名称：

  Synthesis, spectroscopic and structural studies of N-(1H-benzimidazol-2-yl)-N′-benzyl propionamidine

  摘要：

  N-(1H-苯并咪唑-2-基)丙酰亚胺酸乙酯 (1) 与苄胺反应生成相应的 N-(1H-苯并咪唑-2-基)-N′-苄基丙脒 (2)。通过 1H 和 13C NMR 以及 X 射线衍射测定了脒 2 的结构和构象。产物呈单斜晶系，空间群为 P21/c，a=10.7913 埃，b=15.5164 埃，c=9.1130 埃，β=108.378°，Z=4。晶体中存在两个 N-H $\cdots $$ N 氢键，第一个是分子内氢键，将 H4 与 N1 连接起来；第二个是分子间氢键，将 H2 与第二个分子的 N3 连接起来，从而形成与反转有关的二聚体。X 射线结果与半经验计算和非原位计算的结果进行了比较。

  DOI：

  10.1007/s10870-005-9006-z

文献信息

• Reaction of N-2-(1-Carbethoxy) - and N-2-(1-acyl)-benzimidazoimidates with Grignard Reagents. Synthesis of 1,3,5-Oxadiazino-(1,2-a)benzimidazoles
  作者：R. Abderrahim、B. Hajjem、H. Zantour、B. Baccar

  DOI：10.1080/00397919708005009

  日期：1997.9

  Abstract Reaction of ethyl chloroformate and acyl chlorides with iminoesters derived from 2- aminobenzimidazole, followed by Grignard reagent condensation leads to a variety of oxadiazinobenzimidazoles in good yield.

  摘要 氯甲酸乙酯和酰氯与衍生自 2-氨基苯并咪唑的亚氨基酯反应，然后格氏试剂缩合，以良好的收率得到各种恶二嗪基苯并咪唑。
• Synthese De (1,2a)Benzimidazolo-1,3,5,2-triazaphosphorine-2-oxides
  作者：Raoudha Abderrahim、Belgacem Baccar、et Mohamed Lamine Benkhoud

  DOI：10.1080/10426500211735

  日期：2002.5.1

  The reaction of hexamethylphosphotriamide or methylphosphonic bis(dimethylamide) compounds with amidines derived from N-Benzimidazoyl imidates 1 leads to (1,2a)benzimidazolo-1,3,5,2-tiazaphosphorine-2-oxides (4) over bar in good yields. If the condensation is realized at room temperature, N-phosphonic amidines (3) over bar can be isolated as intermediates. The isolated compounds (2) over bar, (3) over bar, and (4) over bar are identified by spectroscopic methods: IR, H-1, C-13, (31)p, NMR, and M.S.
• SYNTHESIS AND REACTVITY OF <i>N</i>-[<i>N</i>-PHOSPHORAMIDO-1<i>H</i>-BENZIMIDAZOL-2-YL] IMIDATES
  作者：Noureddine Raouafi、Khaled Boujlel、Mohamed Lamine Benkhoud

  DOI：10.1080/10426500490485372

  日期：2004.12.1

  N-(-1H-Benzimidazol-2-yl) imidates 1a-c react with chlorophosphoramide to give the N-[-1-N,N,N',N'-tetramethylphosphoramidoyl-1H-benzimidazol-2-yl]-imidates 2a-c or with dichlorophosphoramide to yield the bis[(N-1-benzimidazol-2-yl)-imidate]phosphoramide derivatives 3a-b. The reaction of compounds 2a-c toward primary amines is studied. The obtained amidine derivatives 4a-b were unambiguously characterized by different spectroscopic techniques (IR, H-1, C-13, and P-31 NMR, and in some cases MS).
• Synthesis, spectroscopic and structural studies of N-(1H-benzimidazol-2-yl)-N′-benzyl propionamidine
  作者：N. Raouafi、M. Freytag、P. G. Jones、M. L. BenKhoud

  DOI：10.1007/s10870-005-9006-z

  日期：2007.6

  N-(1H-Benzimidazol-2-yl) propionimidic acid ethyl ester (1) reacts with benzylamine to yield the corresponding N-(1H-Benzimidazol-2-yl)-N′-benzyl proponamidine (2). The structure and conformation of the amidine 2 were determined by 1H and 13C NMR and X-ray diffraction. The product crystallizes in monoclinic system with space group P21/c, a = 10.7913 Å, b = 15.5164 Å, c = 9.1130 Å, β = 108.378° and Z = 4. In the crystal there are two N–H $$ \cdots $$ N hydrogen bonds, the first is intramolecular H-Bond links H4 to N1; the second one is intermolecular and it links H2 to N3 of a second molecule leading to inversion-related dimers. The X-ray results were compared with those obtained by semi-empirical and ab-initio calculations.

  N-(1H-苯并咪唑-2-基)丙酰亚胺酸乙酯 (1) 与苄胺反应生成相应的 N-(1H-苯并咪唑-2-基)-N′-苄基丙脒 (2)。通过 1H 和 13C NMR 以及 X 射线衍射测定了脒 2 的结构和构象。产物呈单斜晶系，空间群为 P21/c，a=10.7913 埃，b=15.5164 埃，c=9.1130 埃，β=108.378°，Z=4。晶体中存在两个 N-H $\cdots $$ N 氢键，第一个是分子内氢键，将 H4 与 N1 连接起来；第二个是分子间氢键，将 H2 与第二个分子的 N3 连接起来，从而形成与反转有关的二聚体。X 射线结果与半经验计算和非原位计算的结果进行了比较。