N-benzyl 2-pyridinecarboximidamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyl 2-pyridinecarboximidamide
• 英文别名: N'-benzylpyridine-2-carboximidamide
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: VZXCONHIWIEMCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl 2-pyridinecarboximidamide 、 苯甲醛 、 二甲基亚砜 在 氧气 、 caesium carbonate 作用下， 120.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以67%的产率得到4,6-diphenyl-2-(pyridin-2-yl)pyrimidine
  参考文献：
  名称：

  Base-promoted formal [4 + 1+1] annulation of aldehyde, N -benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines

  摘要：

  A base-promoted formal [4 + 1+1] annulation of aldehyde, N-benzyl amidine and DMSO was developed, leading to a series of 2,4,6-triaryl pyrimidines in moderate to good yields. Notably, DMSO served as a methine source, which was activated by base rather than either Lewis acid or electrophile. Molecular O-2 was the sole eco-friendly oxidant during this procedure. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2017.11.020
• 作为产物：
  描述：

  2-氰基吡啶 在 ((1,2-bis(diisopropylphosphino)ethane)NiH)2 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 N-benzyl 2-pyridinecarboximidamide
  参考文献：
  名称：

  Ni（0）催化剂从活化腈中合成idine和苯并恶唑

  摘要：

  脒和2-取代的苯并恶唑分别选自N合成-在温和的条件（50℃，48小时，两步）以原子经济的过程，涉及加入甲醇，溶剂的，对腈部分，得到甲基下杂环腈亚胺酸酯和随后在胺存在下的溶剂挤出，得到标题化合物。通过使用[（dippe）Ni（H）] 2（dippe = 1,2-双（二异丙基膦基）乙烷），[Ni（cod）2 ] / dppe或[Ni（ cod）2 ] / P（OPh）3（cod = 1,5-环辛二烯，dppe = 1,2-双（二苯基膦基）乙烷，P（OPh）3＝亚磷酸三苯酯）作为催化剂前体。关于配体，对于给定的底物，即4-氰基吡啶，对于σ供体双齿二元醇，Ni（0）催化体系的最佳性能被发现，而单齿π受体P（OPh）3的效率较低。关于底物，对于给定的Ni-dippe体系，位阻以及更重要的是，底物的吸电子特征控制亚氨酸盐的形成，从而控制am和苯并恶唑的收率。

  DOI：

  10.1021/acscatal.5b00348

文献信息

• PROPANOIC ACID DERIVATIVES AS INTEGRIN INHIBITORS
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：EP1133488A1

  公开（公告）日：2001-09-19
• [EN] PROPANOIC ACID DERIVATIVES AS INTEGRIN INHIBITORS<br/>[FR] DERIVES D'ACIDE PROPANOIQUE UTILISES EN TANT QU'INHIBITEURS DES INTEGRINES
  申请人：CELLTECH THERAPEUTICS LTD

  公开号：WO2000031067A1

  公开（公告）日：2000-06-02

  Propanoic acid derivatives of formula (1) are described: Ar-X1-Ar1-Z-R in which Ar is a nitrogen base containing group; X1 is linker atom or group; Ar1 is an optionally substituted 5- or 6-membered nitrogen-containing aromatic or non-aromatic monocycle; Z is a group -CH(R13)CH2- [in which R13 is an optionally substituted aliphatic, cycloaliphatic, heteroaliphatic, heterocycloaliphatic, aromatic or heteroaromatic group], -C(R?12a)(R13)-CH(R12b¿)- [in which R?12a and R12b¿ together with the carbon atoms to which they are attached form a C¿3-7?cycloalkyl group] or C(R?13¿)=CH-; R is a carboxylic acid (-CO¿2?H) or a derivative or biostere thereof; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of αV integrins to their ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders.
• Base-promoted formal [4 + 1+1] annulation of aldehyde, N -benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines
  作者：Jin Yuan、Jingbo Li、Bingbing Wang、Song Sun、Jiang Cheng

  DOI：10.1016/j.tetlet.2017.11.020

  日期：2017.12

  A base-promoted formal [4 + 1+1] annulation of aldehyde, N-benzyl amidine and DMSO was developed, leading to a series of 2,4,6-triaryl pyrimidines in moderate to good yields. Notably, DMSO served as a methine source, which was activated by base rather than either Lewis acid or electrophile. Molecular O-2 was the sole eco-friendly oxidant during this procedure. (C) 2017 Published by Elsevier Ltd.
• Synthesis of Amidines and Benzoxazoles from Activated Nitriles with Ni(0) Catalysts
  作者：Jorge A. Garduño、Juventino J. Garcı́a

  DOI：10.1021/acscatal.5b00348

  日期：2015.6.5

  Amidines and 2-substituted benzoxazoles were synthesized from N-heterocyclic nitriles under mild conditions (50 °C, 48 h, two steps) in an atom-economical process that involves addition of methanol, the solvent, to a nitrile moiety to yield a methyl imidate and the subsequent extrusion of solvent in the presence of amines to afford the title compounds. Methyl imidate formation was achieved by developing

  脒和2-取代的苯并恶唑分别选自N合成-在温和的条件（50℃，48小时，两步）以原子经济的过程，涉及加入甲醇，溶剂的，对腈部分，得到甲基下杂环腈亚胺酸酯和随后在胺存在下的溶剂挤出，得到标题化合物。通过使用[（dippe）Ni（H）] 2（dippe = 1,2-双（二异丙基膦基）乙烷），[Ni（cod）2 ] / dppe或[Ni（ cod）2 ] / P（OPh）3（cod = 1,5-环辛二烯，dppe = 1,2-双（二苯基膦基）乙烷，P（OPh）3＝亚磷酸三苯酯）作为催化剂前体。关于配体，对于给定的底物，即4-氰基吡啶，对于σ供体双齿二元醇，Ni（0）催化体系的最佳性能被发现，而单齿π受体P（OPh）3的效率较低。关于底物，对于给定的Ni-dippe体系，位阻以及更重要的是，底物的吸电子特征控制亚氨酸盐的形成，从而控制am和苯并恶唑的收率。