N,N-Dimethyl-benzamidine | 39116-58-0

• 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-Dimethyl-benzamidine
• 英文别名: N,N-Dimethyl-benzamidin；N,N-dimethylbenzamidine；N,N-dimethylbenzenecarboximidamide
• CAS: 39116-58-0
• 化学式: C₉H₁₂N₂
• 分子量: 148.208
• InChiKey: LNIGFYSAOIMZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-Dimethyl-benzamidine 、 生成 N,N-Dimethyl-N'-diisopropylborylbenzamidin
  参考文献：
  名称：

  Amidinoboranes

  摘要：

  DOI：

  10.1007/bf00929697
• 作为产物：
  描述：

  N,N-二甲基苯甲酰胺 在 2,2,2-三氯乙酰胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N,N-Dimethyl-benzamidine
  参考文献：
  名称：

  稳定的4-芳基-2-（三氯甲基）-1,3-二氮杂-1,3-丁二烯的合成及晶体结构

  摘要：

  摘要 一种简单方便的方法，可以从芳基（氯）甲基铵盐（最著名的是Vilsmeier-Haack试剂）和三氯乙am中生成4-芳基取代的1 H -2-（三氯甲基）-1,3-二氮杂1,3-丁二烯已经被开发出来。这些4-芳基-1 H -1,3-二氮杂丁二烯是可分离的，在硅胶色谱法中相对稳定，并且可以结晶。通过X射线衍射分析表明，在固体状态下这些1,3- diazabutadienes具有小号- cisoid构象。这些1，3-二氮杂丁二烯的​​主要特征是它们对缺电子乙炔的反应性，它们在温和的反应条件下反应，以高收率产生4-芳基-2-（三氯甲基）嘧啶。 一种简单方便的方法，可以从芳基（氯）甲基铵盐（最著名的是Vilsmeier-Haack试剂）和三氯乙am中生成4-芳基取代的1 H -2-（三氯甲基）-1,3-二氮杂1,3-丁二烯已经被开发出来。这些4-芳基-1 H -1,3-二氮杂丁二烯是可分离的，在

  DOI：

  10.1055/s-0035-1561936

文献信息

• [EN] METAL COMPLEX COMPRISING AMIDINE AND INDOLE FUSED CYCLOPENTADIENYL LIGANDS<br/>[FR] COMPLEXE MÉTALLIQUE COMPRENANT DES LIGANDS DE CYCLOPENTADIÉNYLE FUSIONNÉS PAR AMIDINE ET INDOLE
  申请人：ARLANXEO NETHERLANDS BV

  公开号：WO2019201838A1

  公开（公告）日：2019-10-24

  A metal complex of the formula (1) InCyLMZp (1), wherein M is a group 4 metal Z is an anionic ligand, p is number of 1 to 2, preferably 2, InCy is an indole fused cyclopentadienyl-type ligand of the formula (2) wherein R1 means for each index m individually a C1-C4-alkyl that substitutes a hydrogen atom of the benzene ring, m is a number of 0 to 4, preferably 0 to 2, in particular 0, R2 means C1-C10-alkyl, C5- C10-cycloalkyl, and an unsubstituted or C1-C10-alkyl or C1-C4-dialkyl amino substituted C6-C10-aryl, in particular C1-C4-20 alkyl substituted phenyl, more preferably methyl, phenyl or di-C1-C4-alkyl substituted phenyl, in particular di-tert.-butyl-phenyl, R3, R4 and R5 being individually selected from the group of hydrogen, C1-C4-alkyl, unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aryl, in particular unsubstituted or C1-C4-alkyl substituted phenyl whereby preferably R3, R4 and R5 being individually selected from the group of hydrogen, C1-C4-alkyl, unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aryl, in particular C1-C4-alkyl substituted phenyl, more preferably at least one of the radicals R3 to R5 shall mean C1-C4-alkyl, in particular methyl, i-propyl and phenyl and, L is an amidinate ligand of the formula (3) (3) wherein the amidine-containing ligand is covalently bonded to the metal M via the imine nitrogen atom, and Sub1 is an unsubstituted or C1-C4-alkyl and/or halogen, in particular chlorine or fluorine substituted C6-C10-aromatic substituent, in particular phenyl and Sub2 is a substituent comprising a heteroatom of group 15, through which Sub2 is bonded to the imine carbon atom or Sub1 and Sub2 together with the imino group they are connected to form a ligand of formula (3a) wherein the amidine-containing ligand (3a) is covalently bonded to the metal M via the imine nitrogen atom N2, wherein the benzo ring fused to the amidine ring may be unsubstituted or contain further substituents R7, which are individually of the index "q" selected from the group of hydrogen, C1-C4-alkyl and halogen and whereby q is a number of 0 to 4, preferably 0 to 2, most preferably 0, Sub4 is an aliphatic or aromatic cyclic or linear substituent comprising a group 14 atom through which Sub4 is bonded to the amino nitrogen atom N 1, preferably Sub4 is a C6-C10-aromatic ring, preferably phenyl which is unsubstituted or substituted by one or more substituents from the group selected from halogen, in particular Cl or F and C1-C4-alkyl, preferably Sub4 is a 2,6-di-fluorophenyl.

  化合物的化学式为：InCyLMZp，其中M是第4族金属，Z是一个阴离子配体，p是1到2之间的数字，最好是2。InCy是一个融合苯环的吲哚基环戊二烯基配体，其化学式为：R1代表每个指数m分别为苯环的C1-C4烷基取代氢原子，m的取值范围为0到4，最好是0到2，特别是0。R2代表C1-C10烷基、C5-C10环烷基，以及未取代或取代的C1-C10烷基或C1-C4二烷基氨基取代的C6-C10芳基，特别是C1-C4-20烷基取代的苯基，更好的是甲基、苯基或二甲基取代的苯基，特别是叔丁基二甲基取代的苯基。R3、R4和R5分别选自氢、C1-C4烷基、未取代或C1-C4烷基和/或卤素，特别是氯或氟取代的C6-C10芳基，特别是未取代或C1-C4烷基取代的苯基，最好是R3、R4和R5中至少有一个代表C1-C4烷基，特别是甲基、异丙基和苯基。L是一个含有酰胺基的配体的化学式，其中该酰胺基配体通过亚胺氮原子与金属M共价结合，Sub1是未取代或C1-C4烷基和/或卤素，特别是氯或氟取代的C6-C10芳基，特别是苯基，Sub2是一个含有第15族元素的取代基，通过这个取代基与亚胺碳原子或Sub1结合，Sub2与亚胺基一起形成一个配体的化学式，其中含有酰胺基的配体通过亚胺氮原子N2与金属M共价结合，其中与酰胺环融合的苯环可能是未取代的或含有进一步的取代基R7，这些取代基分别为指数“q”选自氢、C1-C4烷基和卤素，q的取值范围为0到4，最好是0到2，最好是0，Sub4是通过含有第14族元素的线性或环状取代基与氨基氮原子N1结合的取代基，最好是C6-C10芳环，最好是未取代或由卤素（特别是Cl或F）和C1-C4烷基中的一个或多个取代的苯基，最好是2,6-二氟苯基。
• Amido-derivatives of metals and metalloids. Part X. Reactions of titanium(IV), zirconium(IV), and hafnium(IV) amides with unsaturated substrates, and some related experiments with amides of boron, silicon, germanium, and tin(IV)
  作者：G. Chandra、A. D. Jenkins、M. F. Lappert、R. C. Srivastava

  DOI：10.1039/j19700002550

  日期：——

  Insertion reactions of amides LM–(NR2)n with the dipoles AB to give the adducts LM(NR2)n – x(A–B–NR2)x are described. The amides included the Group IVA [M(NMe2)4(M = Ti, Zr, or Hf)] and IVB [Me3M·NMe2(M = Si, Ge, or Sn)] compounds and o-C6H4O2B·NEt2, while the dipoles were PhNCO, PhNCS, MeNCS, p-MeC6H4·N:C:N·C6H4Me-p, C6H11·N:C:N·C6H11, MeO2C·C:C·CO2Me, CO2, CS2, CH2:CH·CN, PhCN, p-MeC6H4·CN, CH2:CCl(CN)

  描述了酰胺LM–（NR 2）n与偶极AB的插入反应，得到加合物LM（NR 2）n – x（AB–NR 2）x。酰胺包括IVA族[M（NMe 2）4（M = Ti，Zr或Hf）]和IVB [Me 3 M·NMe 2（M = Si，Ge或Sn）]化合物和o -C 6 H 4 O 2 B·NEt 2，而偶极子是PhNCO，PhNCS，MeNCS，p -MeC 6 H 4 ·N：C：N·C 6 H 4 Me-p，C 6 H 11 ·N：C：N·C 6 H 11，MeO 2 C·C：C·CO 2 Me，CO 2，CS 2，CH 2：CH·CN，PhCN，p -MeC 6 H 4 ·CN，CH 2：CCl（CN），C 6 F 5 ·CN，CCl 3 ·CN，[省略图示]和MeCH：CH·CHO。讨论的问题是反应的化学计量学，加合物的结构以及各种酰胺和偶极的相对反应性。
• Amidino Pentadienylium Salts − A New Cyanine Dye Type
  作者：Marie-Pierre Fialon、Alexander Chernega、Vadim Romanenko、Marie-Rose Mazières、Jean-Gérard Wolf

  DOI：10.1002/(sici)1099-0690(199802)1998:2<329::aid-ejoc329>3.0.co;2-z

  日期：1998.2

  The reactivity of carboxonium salts permits substitution of one or both of the reactive terminal ethoxy groups by amidino moieties. In this way, new cyanine dyes with extended conjugation paths are obtained. These have been studied by UV/vis spectrophotometry. Furthermore, the X-ray structure of 1b has been determined and compared with that predicted by molecular mechanical calculations.

  碳鎓盐的反应性允许一个或两个反应性末端乙氧基被脒基部分取代。通过这种方式，获得了具有扩展共轭路径的新花青染料。这些已经通过紫外/可见分光光度法进行了研究。此外，已经确定了 1b 的 X 射线结构，并与分子力学计算预测的结构进行了比较。
• Tandem Synthesis of 10-Dimethylaminobenzo[<i>h</i>]quinazolines from 2-Ketimino-1,8-bis(dimethylamino)naphthalenes via Nucleophilic Replacement of the Unactivated Aromatic NMe₂ Group
  作者：Vladimir Y. Mikshiev、Alexander S. Antonov、Alexander F. Pozharskii

  DOI：10.1021/acs.orglett.6b01178

  日期：2016.6.17

  a result of [2 + 2 + 2] nucleophilic cascade annulation produces 10-dimethylaminobenzo[h]quinazolines, as yet unknown NMe2/–N═ analogues of the proton sponge. It is even more convenient to use preliminarily prepared 2-ketimino-1,8-bis(dimethylamino)naphthalenes as starting material. The substitution of both peri-NMe2 groups furnishing quinazolino[7,8-h]quinazoline derivatives is also possible. The process

  已经发现，由于[2 + 2 + 2]亲核反应，用n -BuLi和2当量相同或不同的芳基（杂芳基）氰化物顺序处理2-溴-1,8-双（二​​甲基氨基）萘级联成环产生10-二甲基氨基苯并[ h ]喹唑啉，作为质子海绵的未知的NMe 2 / –N═类似物。使用预先制备的2-酮亚氨基-1,8-双（二​​甲基氨基）萘作为起始原料甚至更加方便。两者的取代围-NMe 2个基团家具quinazolino [7,8- ħ ]喹唑啉衍生物也是可能的。通过未活化的芳族NMe 2的轻度亲核取代，该过程非常出色 团体。
• [EN] METAL COMPLEX COMPRISING AMIDINE AND SUBSTITUTED CYCLOPENTADIENYL LIGANDS<br/>[FR] COMPLEXE MÉTALLIQUE COMPRENANT DE L'AMIDINE ET DES LIGANDS CYCLOPENTADIÉNYLE SUBSTITUÉS
  申请人：LANXESS ELASTOMERS BV

  公开号：WO2016041818A1

  公开（公告）日：2016-03-24

  A metal complex of the formula (1 ) CyLMZp(A)n (1 ), wherein M is a group 4 metal Z is an anionic ligand, p is number of 1 to 2, preferably 2, Cy is a cyclopentadienyl-type ligand substituted with at least one aliphatic C3-C20 hydrocarbyl group, which is bonded to the cyclopentadienyl-type ligand, in particular to its cyclopentadienyl ring, via a secondary, a tertiary or quaternary carbon atom and, L is an amidinate ligand of the formula (2), wherein the amidine-containing ligand is covalently bonded to the metal M via the imine nitrogen atom, and Sub1 is a substituent comprising a group 14 atom through which Sub1 is bonded to the imine carbon atom and Sub2 is a substituent comprising a heteroatom of group 15, through which Sub2 is bonded to the imine carbon atom and A is a neutral Lewis base ligand selected from the list consisting of ether, thioether, amine, tertiary phosphane, imine, nitrile and isonitrile,wherein the number of said metal ligands "n" is in the range of 0 to the amount that specifies the 18-electron rule.

  一种化学配合物的化学式（1）CyLMZp（A）n（1），其中M是4族金属，Z是一个阴离子配体，p是1至2的数字，最好是2，Cy是一种环戊二烯基类型的配体，其上至少有一个与环戊二烯基类型配体上的一个次生、三次或四次碳原子键合的脂肪烃基，L是一个化学式（2）的氨基酰配体，其中含有氨基的配体通过亚胺氮原子与金属M共价键合，Sub1是一个含有14族元素的取代基，通过Sub1与亲胺碳原子键合，Sub2是一个含有15族元素的取代基，通过Sub2与亲胺碳原子键合，A是从醚、硫醚、胺、三级膦、亚胺、腈和异腈的列表中选择的中性路易斯碱配体，其中金属配体“n”的数量在0到符合18电子规则的数量范围内。