N,N'-di-p-tolylbenzamidine | 13471-34-6

• 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: N,N'-di-p-tolylbenzamidine
• 英文别名: N,N'-ditolylbenzamidine；N,N'-di-p-tolylbenzimidamide；N,N'-Di-p-tolyl-benzamidin；N,N'-di-p-methylphenylbenzamidine；N,N'-bis(4-methylphenyl)benzenecarboximidamide
• CAS: 13471-34-6
• 化学式: C₂₁H₂₀N₂
• 分子量: 300.403
• InChiKey: XGOYIAMBHATZQR-UHFFFAOYSA-N

物化性质

• 熔点：
  127-130 °C
• 沸点：
  472.7±38.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N'-di-p-tolylbenzamidine 在 sodium hydroxide 作用下， 以 甲醇 、 苯 为溶剂， 反应 49.0h， 生成
  参考文献：
  名称：

  摘要：

  A procedure has been developed for the synthesis of N-cyclopentadienyl amidinium ylides of the general formula C-5(CO2Me)(4)[ArNC(Ar)NHAr]. According to the X-ray diffraction data, H-1 and C-13 NMR spectroscopy, and MNDO quantum-chemical calculations, the title compounds have a zwitterionic structure with the positive charge localized over the amidine N-C-N triad, and the negative charge, over the cyclopentadiene fragment. The configuration of the amidine moiety is stabilized by additional interaction of the NH hydrogen atom with the negatively charged cyclopentadiene ring (pi-bonding). The ylides are chiral due to atropoisomerism arising from a high energy barrier (DeltaG(298)(not equal) > 25 kcal/mol) to rotation of the Ar' substituent about the ordinary C-C bond in the amidinium fragment.

  DOI：

  10.1023/a:1020897411534
• 作为产物：
  描述：

  苯并-p-甲苯胺 在 五氯化磷 作用下， 生成 N,N'-di-p-tolylbenzamidine
  参考文献：
  名称：

  Just, Chemische Berichte, 1886, vol. 19, p. 983

  摘要：

  DOI：

文献信息

• Synthesis of Amides and Amidines by Reaction of Carboxylic Acids and Amines in the Presence of Polyphophoric Acid Trimethylsilyl Ester (PPSE)
  作者：Shin-ichi Ogata、Amane Mochizuki、Masa-aki Kakimoto、Yoshio Imai

  DOI：10.1246/bcsj.59.2171

  日期：1986.7

  The reaction between amines and carboxylic aicds in the presence of polyphosphoric acid trimethylsilyl ester (PPSE) has been investigated from the view point of the synthesis of amides and amidines. Benzanilide was selectively prepared from benzoic acid and aniline in the presence of PPSE and pyridine at 100 °C, whereas a mixture of benzanilide and N,N′-diphenylbenzamidine was obtained without the

  从合成酰胺和脒的角度研究了胺和羧酸在多磷酸三甲基甲硅烷基酯（PPSE）存在下的反应。在 PPSE 和吡啶的存在下，在 100°C 下，苯甲酸和苯胺有选择地制备苯甲酰苯胺，而在不使用吡啶的情况下获得苯甲酰苯胺和 N,N'-二苯基苯甲脒的混合物。在 160 °C 下的反应几乎完全得到 N,N'-二苯基苯甲脒。通过简单地在 160 °C 下与四摩尔量的 PPSE 加热，可以从羧酸和芳香胺的组合中以高产率获得各种对称脒。在相同条件下，脂肪族和芳香族胺与 N-单取代和 N,N-二取代酰胺的反应也得到相应的不对称脒。
• Application of the copper catalysed N-arylation of amidines in the synthesis of analogues of the chemical tool, blebbistatin
  作者：Christopher P. A. T. Lawson、Alexandra M. Z. Slawin、Nicholas J. Westwood

  DOI：10.1039/c0cc03624b

  日期：——

  A robust protocol for the CuI-catalysed arylation of amidines is presented. Whilst the initially identified conditions were useful for benzamidine-derived substrates, difficulties were encountered with more complex substrates. This problem was overcome following a change in ligand type, enabling the synthesis of analogues of the chemical tool, blebbistatin.

  我们提出了一种可靠的铜碘催化酰胺的芳基化协议。尽管最初确定的条件对苯酰胺衍生物很有效，但在处理更复杂的底物时遇到了困难。通过更换配体类型，解决了这个问题，从而实现了化学工具区育素（blebbistatin）类似物的合成。
• Cyclopentadienyl-Like Ligand as a Reactive Site in Half-Sandwich Bis(amidinato) Rare-Earth-Metal Complexes: An Efficient Application in Catalytic Addition of Amines to Carbodiimides
  作者：Peng-Hui Wei、Ling Xu、Li-Cheng Song、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/om5002793

  日期：2014.6.9

  excellent catalytic activity for the addition of amines to carbodiimides, yielding the corresponding guanidines. Isolation, structural characterization, and catalytic application of the binuclear lutetium amido complex showed clearly that the catalytic cycle was initiated by the dissociation of Cp′. These results demonstrated that Cp′, for the first time, acted as a reactive site to yield the active Ln–N

  一系列混合Cp的'/双（amidinato）（CP'=η 5 -C 5我4（森达3））镧系络合物通过1合成：Cp'Ln（CH 2之间的酸-碱反应2森达3）2（THF）（Ln为Y，镝，铒，Lu）和脒。这些CP'/双（amidinato）络合物显示出优异的催化活性的加成胺制碳二亚胺，得到相应的胍。双核酰胺配合物的分离，结构表征和催化应用清楚地表明，催化循环是由Cp'的解离引发的。这些结果表明，CP'，对于第一次，充当反应部位产生活性LN-N物种。
• Chloroboration and allied reactions of unsaturated compounds. Part IV. Boration of di-p-tolylcarbodi-imide
  作者：R. Jefferson、M. F. Lappert、B. Prokai、B. P. Tilley

  DOI：10.1039/j19660001584

  日期：——

  high yields of novel borylenebisamidines, boryl-amidines and -guanidines and related compounds, (I), (II), (III), and (IV). These reactions are insertions into the B–X (X = Cl, Br, Ph, OMe, NEt2, or SBun) bond. The synthesis of (III) and (IV) shows that under more forcing conditions it is possible to effect the insertion of more than 1 mol. of a 1 : 2 dipole into the B–X bond. Aminoboration with amine

  二对甲苯基碳二亚胺与许多硼烷[BCl 3，BBr 3，MeOBCl 2，（MeO）2 BCl，o -C 6 H 4 O 2 B·SBu n，o -C 6 H 4 O 2反应B·NEt 2，（Et 2 N）2 BCl，PhBCl 2，PhB（OMe）2，PhB（NEt 2）SBu n，Ph 2 BCl，Ph 2 B·OMe，Ph 2 B·SBu n，Ph 2 B·NEt 2和Ph 3 B]的条件下，可高收率地合成新型的亚苄基双am，硼烷基-and和-胍以及相关的化合物，（I），（II），（III）和（IV） 。这些反应是插入到B–X键中（X = Cl，Br，Ph，OMe，NEt 2或SBu n）。（III）和（IV）的合成表明，在更强的条件下，可以进行大于1mol的插入。1：2偶极子进入B–X键。氨基消除氨基硼化提供了通往1,3,5,2-三氮杂硼烷（V）的途径。
• Orthometallated amidine complexes of palladium, platinum and nickel(<scp>II</scp>). Crystal structure of [Pd{p-CH₃C₆H₄NC-(CH₃)NHC₆H₃CH₃-p}(η⁵-C₅H₅)]
  作者：James Barker、Neil D. Cameron、Melvyn Kilner、Mouayed M. Mahmoud、Stephen C. Wallwork

  DOI：10.1039/dt9910003435

  日期：——

  η5-cyclopentadienyl, acetylacetonato, aceto-, benzamidino-, and allyl complexes, which retain the orthometallated amidino-group. Treatment of the chloride-bridged platinum complexes with CO under pressure causes carbonylation to form [PtR′NC(R)C6H3R″}(CO)Cl], whereas for palladium cleavage of the orthometallated ligand from the metal occurs with formation of the corresponding quinazolin-4-one. The six-membered nature

  在甲醇水溶液中，K 2 [MCl 4 ]（M = Pd或Pt）与具有芳基取代基的甲form，乙am和苯am [R'NHC（R）NR']反应形成微溶的正金属配合物。N，N'-二芳基甲am和-乙am形成六元金属环[M [R'NC（R）NH-C 6 H 3 R''] Cl} n ]，而对于N，N'-二芳基苯甲having具有同时产生了N-和C-芳基取代基五元金属环[M [R'NC（C 6 H 4）NHR'] Cl} n ]。相关配合物由Np的反应形成-K 2 [PdCl 4 ]-对甲苯乙酰胺和对乙酰苯胺。在溶液中加热时的加合物[M R'NC（R）-NHR'} Cl 2 ]也产生原金属化的配合物。低聚的氯化物桥/聚合物材料被切割以得到吡啶和二甲亚砜的加合物，而氯配体引线的位移到η 5 -环戊二烯基，乙酰丙酮，aceto-，benzamidino-和烯丙基络合物，其保留orthometalla