N,N'-(ethane-1,2-diyl)bis(N-methylbenzamide) | 24768-61-4

• 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'-(ethane-1,2-diyl)bis(N-methylbenzamide)
• 英文别名: N,N′-(ethane-1,2-diyl)bis(N-methylbenzamide)；N,N'-Dimethyl-N,N'-dibenzoylaethylendiamin；N,N'-dimethyl-N,N'-ethanediyl-bis-benzamide；N,N'-Dimethyl-N,N'-aethandiyl-bis-benzamid；N-[2-[benzoyl(methyl)amino]ethyl]-N-methylbenzamide
• CAS: 24768-61-4
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: GKJNYSVSIQKNEV-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C(Solv: benzene (71-43-2))
• 沸点：
  493.5±28.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-(ethane-1,2-diyl)bis(N-methylbenzamide) 在 三氢化钐 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以62%的产率得到1,4-Dimethyl-5,6-diphenyl-1,2,3,4-tetrahydro-pyrazine
  参考文献：
  名称：

  Ogawa, Akiya; Takami, Noriaki; Sekiguchi, Masahito, Journal of the American Chemical Society, 1992, vol. 114, # 22, p. 8729 - 8730

  摘要：

  DOI：
• 作为产物：
  描述：

  安息香精油 在 acid polystyrene-immobilized Rose Bengal 、 二苄叉丙酮 作用下， 以 二氯甲烷 、 邻二甲苯 为溶剂， 生成 N,N'-(ethane-1,2-diyl)bis(N-methylbenzamide)
  参考文献：
  名称：

  杂原子取代基对1,2-二氧杂环丁烷性能的影响

  摘要：

  与相应的含氧二氧杂环丁烷相比，氮和硫取代的二氧杂环丁烷显示出极低的分解活化能。提出了一种涉及分子内电子转移过程的机制，用于裂解这些不稳定的二氧杂环丁烷。

  DOI：

  10.1016/s0040-4039(00)98147-4

文献信息

• Substituent effects on axle binding in amide pseudorotaxanes: comparison of NMR titration and ITC data with DFT calculations
  作者：Lena Kaufmann、Egor V. Dzyuba、Friedrich Malberg、Nora L. Löw、Matthias Groschke、Boris Brusilowskij、Juhani Huuskonen、Kari Rissanen、Barbara Kirchner、Christoph A. Schalley

  DOI：10.1039/c2ob25196e

  日期：——

  The binding behaviour of differently substituted diamide axle molecules to Hunter/Vögtle tetralactam macrocycles was studied with a combination of NMR titration, isothermal titration calorimetry (ITC) experiments and calculations employing density functional theory (DFT), along with dispersion-corrected exchange-correlation functionals. Guests with alkyl or alkenyl chains attached to the diamide carbonyl groups have a significantly higher binding affinity to the macrocycle than guests with benzoyl amides and their substituted analogues. While the binding of the benzoyl and alkenyl substituted axles is enthalpically driven, the alkyl-substituted guest binds mainly because of a positive binding entropy. The electronic effects of para-substituents at the benzoyl moieties have an influence on the binding affinities. Electron donating substituents increase, while electron-withdrawing substituents decrease the binding energies. The binding affinities obtained from both NMR titration and ITC experiments correlate well with each other. The substituent effects observed in the experimental data are reflected in adiabatic interaction energies calculated with density functional methods. The calculated structures also agree well with pseudorotaxane crystal structures.

  不同取代的二酰胺轴分子与Hunter/Vögtle四内酯大环的结合行为通过NMR滴定、等温滴定量热法（ITC）实验以及采用密度泛函理论（DFT）和修正了色散的交换-关联泛函的计算进行了研究。与苯甲酰胺及其取代类似物相比，带有烷基或烯基链连接到二酰胺羰基的客体对大环的结合亲和力显著更高。苯甲酰和烯基取代的轴的结合主要是由焓驱动，而烷基取代的客体主要是因为正的结合熵。苯甲基部分的对位取代基的电子效应会影响结合亲和力。给予电子的取代基增加结合能，而吸电子的取代基则降低结合能。通过NMR滴定和ITC实验获得的结合亲和力彼此之间有很好的相关性。实验数据中观察到的取代基效应在用密度泛函方法计算的绝热相互作用能中得到了反映。计算出的结构也与伪旋转烷晶体结构相一致。
• Selective Monoacylation of Symmetrical Diamines via Prior Complexation with Boron
  作者：Zhongxing Zhang、Zhiwei Yin、Nicholas A. Meanwell、John F. Kadow、Tao Wang

  DOI：10.1021/ol0300773

  日期：2003.9.1

  [reaction: see text] Pretreatment of a symmetrical primary or secondary diamine with 9-BBN prior to the addition of an acyl chloride significantly suppressed undesired diacylation, and the product of monoacylation predominated. The reactive preference is interpreted as the result of a selective deactivation of one nitrogen atom of the diamine by 9-BBN.

  [反应：见正文]在添加酰氯之前，用9-BBN预处理对称的伯或仲二胺会显着抑制不希望的二酰化作用，并且单酰化产物占主导地位。反应性偏爱被解释为二胺的一个氮原子被9-BBN选择性失活的结果。
• Imidazole-Catalyzed Monoacylation of Symmetrical Diamines
  作者：Sanjeev K. Verma、B. N. Acharya、M. P. Kaushik

  DOI：10.1021/ol101604q

  日期：2010.10.1

  An imidazole-catalyzed protocol for monoacylation of symmetrical diamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.

  已经开发了咪唑催化的对称二胺单酰基化方案。该方案给出了脂族（环状和无环）伯和仲二胺的选择性单酰化作用。在反应中，咪唑既充当催化剂又充当离去基团。在乙醇/水溶剂体系中，在室温下合成了不同的单酰化哌嗪和其他二胺。
• Access to (<i>Z</i>)-1,2-Endiamides and 1,1-Endiamides via a Base-Promoted Tandem Reaction
  作者：Zhenming Zhang、Bei Fu、Hui Wang、Han Chen、Yongliang Tu、Junfeng Zhao

  DOI：10.1021/acs.joc.9b03305

  日期：2020.4.17

  An efficient base-promoted tandem reaction between vinyl 1,1-dichlorides and secondary sulfonamides with ynamide as the key intermediate is described. This method provides a facile approach to (Z)-1,2-endiamide and aryl 1,1-endiamide derivatives via the β-hydroamidation of terminal ynamides and the α-hydroamidation of internal ynamides, respectively. This reaction proceeded through double elimination

  描述了乙烯基1，1-二氯化物与仲磺酰胺之间以乙酰胺为主要中间体的有效碱促进的串联反应。该方法分别通过末端乙酰胺的β-氢酰胺化和内部乙酰胺的α-氢酰胺化提供了一种简便的方法来合成（Z）-1,2-二酰胺和芳基1,1-二酰胺衍生物。该反应通过两次消除氯乙烯和向亲炔两次添加亲核试剂而进行。另外，它具有容易获得的起始原料，温和的反应条件，广泛的底物范围，广泛的官能团耐受性和操作便利性。
• Some Features of Phosphorylation and Benzoylation of Pyridoxal Imidazolidines
  作者：L. K. Kibardina、A. V. Trifonov、A. B. Dobrynin、M. A. Pudovik、A. R. Burilov

  DOI：10.1134/s1070363221090097

  日期：2021.9