N,N'-(propane-1,3-diyl)dibenzamide | 68388-03-4

• 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'-(propane-1,3-diyl)dibenzamide
• 英文别名: N,N'-dibenzoyl-1,3-propylenediamine；N,N'-trimethylenebis(benzamide)；N,N'-trimethylenedibenzamide；1,3-bis(benzamido)propane；N,N'-propanediyl-bis-benzamide；N,N'-Propandiyl-bis-benzamid；N-[3-(benzoylamino)propyl]benzamide；N-(3-benzamidopropyl)benzamide
• CAS: 68388-03-4
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: MLGLVNOARCEYHW-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  588.7±33.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)
• 溶解度：
  >42.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-(propane-1,3-diyl)dibenzamide 生成 2-苯基-1,4,5,6-四氢嘧啶
  参考文献：
  名称：

  Hofmann,A. W., Chemische Berichte, 1888, vol. 21, p. 2336

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基-1,4,5,6-四氢嘧啶 在 alkali 、 aqueous alkali 作用下， 生成 N,N'-(propane-1,3-diyl)dibenzamide
  参考文献：
  名称：

  Branch; Titherley, Journal of the Chemical Society, 1912, vol. 101, p. 2352

  摘要：

  DOI：

文献信息

• Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
  作者：Yu-Chao Yuan、Raghu Kamaraj、Christian Bruneau、Thierry Labasque、Thierry Roisnel、Rafael Gramage-Doria

  DOI：10.1021/acs.orglett.7b03278

  日期：2017.12.1

  The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

  使用钌催化剂，以高收率和较短的反应时间实现了单步操作中各种合成吸引力的邻苯二甲酰亚胺前所未有的转化为酰胺。机理研究表明，独特的均质途径涉及五元环的打开和CO 2的释放，其中水是质子的来源。
• Chiral phosphinamides: new catalysts for the asymmetric reduction of ketones by borane
  作者：Barry Burns、N. Paul King、Heather Tye、John R. Studley、Mark Gamble、Martin Wills

  DOI：10.1039/a709174e

  日期：——

  We have identified a new class of catalysts for the asymmetric reduction of prochiral ketones by borane. Key to the architecture of effective catalysts is an N–PO structural unit which may be part of a phosphinamide, phosphonamide or a related structure. Such catalysts are simple to prepare, are often crystalline solids and may be recovered from reduction reactions and reused. The catalysts act essentially

  我们已经鉴定出一类新的催化剂，用于硼烷不对称还原前手性酮。有效催化剂结构的关键是N–P O结构单元，它可能是次膦酰胺，膦酰胺或相关结构的一部分。这种催化剂易于制备，通常为结晶固体，可以从还原反应中回收并再利用。催化剂基本上起路易斯碱的作用，通过给电子增加硼烷的反应性。在与硼烷反应时，将羟基引入催化剂中提供了相邻的路易斯酸位点，因此提供了能够不对称引发高达92％ee的优异催化剂。
• N,N?-Diacylated imidazolidines and hexahydropyrimidines
  作者：O. A. Luk'yanov、G. V. Pokhvisneva、T. V. Ternikova

  DOI：10.1007/bf00703698

  日期：1994.8

  A method for the preparation ofN-monoacyl imidazolidines and hexahydropyrimidines (as hydrochlorides) by interaction of monoacylated derivatives of ethylenediamine and trimethylenediamine with chloromethyl methyl ether was developed. Also a method for the preparation ofN,N′-diacylimidazolidines and hexahydropyrimidines either by acylation of their monoacyl derivatives or by reaction of the correspondingN

  开发了一种通过乙二胺和三亚甲基二胺的单酰化衍生物与氯甲基甲醚相互作用制备N-单酰基咪唑烷和六氢嘧啶（作为盐酸盐）的方法。还有一种制备 N,N'-二酰基咪唑烷和六氢嘧啶的方法，通过它们的单酰基衍生物的酰化或通过相应的 N,N'-二酰基亚烷基二胺衍生物与二甲氧基甲烷、二乙酰氧基甲烷、1,3,5-三恶烷或氯甲基甲醚的反应被设计。
• Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N-H/C-H Arylation
  作者：Biswadip Banerji、Satadru Chatterjee、K. Chandrasekhar、Chinmay Nayan、Sunil Kumar Killi

  DOI：10.1002/ejoc.201701039

  日期：2017.9.25

  A palladium-catalyzed direct synthesis of phenanthridones from benzamides in a single step with yields up to 87 % is reported. The method does not require directing groups or harsh conditions and has a wide functional group tolerance.

  据报道，钯催化一步反应从苯甲酰胺直接合成菲咯烷酮，产率高达87％。该方法不需要指导基团或苛刻的条件，并且具有宽泛的官能团耐受性。
• Stabilized well-dispersed Pd(0) nanoparticles for aminocarbonylation of aryl halides
  作者：Yinghuai Zhu、Li Chuanzhao、Algin Oh Biying、Meriska Sudarmadji、Anqi Chen、Dang Thanh Tuan、Abdul M Seayad

  DOI：10.1039/c1dt10927h

  日期：——

  Well-dispersed palladium (0) nanoparticles stabilized with phosphonium based ionic liquid were synthesized conveniently and fully characterized. A catalyst system comprising of the Pd(0) nanoparticles and a base was found to be recyclable and efficient for the aminocarbonylation reaction of aryl iodide in ionic liquid media. In the presence of potassium tert-butyloxide, for the relatively stable aryl chloride and bromide substrates, medium activities were achieved for the catalyst. The catalyst composites can be recycled at least five times with sustained activity.

  很好分散的镍(0)纳米颗粒使用基于膦的离子液体进行合成，并进行了全面表征。由Pd(0)纳米颗粒和碱组成的催化剂系统被发现对于离子液体介质中芳基碘化物的氨基羰基化反应具有可回收性和高效性。在存在氟化钾叔丁基氧化物的情况下，对于相对稳定的芳基氯和溴底物，催化剂显示出中等活性。催化剂复合材料至少可以回收五次且保持活性。