N-acetyl-N'-(p-chlorophenyl)-1,3-diaminopropane | 208724-68-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-acetyl-N'-(p-chlorophenyl)-1,3-diaminopropane
• 英文别名: N-[3-(4-chloroanilino)propyl]acetamide
• CAS: 208724-68-9
• 化学式: C₁₁H₁₅ClN₂O
• 分子量: 226.706
• InChiKey: HQLYQLAMXVTYMM-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  461.118±25.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.176±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-acetyl-N'-(p-chlorophenyl)-1,3-diaminopropane 在 三甲基硅基二氢化磷酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以77%的产率得到1-(4-chlorophenyl)-2-methyl-5,6-dihydro-4H-pyrimidine
  参考文献：
  名称：

  1-芳基-2-烷基-1,4,5,6-四氢嘧啶的合成与性质

  摘要：

  描述了通过用多甲基三甲基甲硅烷基环化N-酰基-N'-芳基三亚甲基二胺2来合成1-芳基-2-烷基-1,4,5,6-四氢嘧啶1的通用方法。前体2通过相应的N-（3-溴丙基）酰胺3的氨解获得。分析了四氢嘧啶1的1 H nmr光谱，讨论了杂环1和2位上取代基的影响。化合物1的碱性水解，仅源于N-酰基-N'-芳基三亚甲基二胺2还通过中间体甲醇胺进行了研究。根据立体电子控制理论讨论了这种中间体的裂解。用硼烷还原化合物1会导致区域特异性地导致N-烷基-N'-芳基三亚甲基二胺6。

  DOI：

  10.1002/jhet.5570360116
• 作为产物：
  描述：

  N-(pchlorophenyl)-1,3-propanediamine 、 乙酸酐 在 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以84%的产率得到N-acetyl-N'-(p-chlorophenyl)-1,3-diaminopropane
  参考文献：
  名称：

  Selective Monoformylation Of 1,3-Diaminopropane Derivatives

  摘要：

  A general procedure for regiospecific construction of N-aryl-N'-formyl-1,3-diaminopropanes 2 (R=H) by selective monoformylation of N-(3-aminopropyl)arylamines 1 is described. Compounds 1 are readily obtained with high yields by aminolysis of 3-bromopropylamine hydrobromide with aromatic amines. The present synthetic strategy was extended to the synthesis of other Nacyl-N'-aryl-1,3-diaminopropanes.

  DOI：

  10.1080/00397919908086172

文献信息

• Synthesis and properties of 1-aryl-2-alkyl-1,4,5,6-tetrahydropyrimidines
  作者：Liliana R. Orelli、Fernando Niemevz、María B. García、Isabel A. Perillo

  DOI：10.1002/jhet.5570360116

  日期：1999.1

  N-acyl-N′-aryltrimethylenediamines 2 with trimethylsilyl polyphosphate. Precursors 2 were obtained by aminolysis of the corresponding N-(3-bromopropyl)amides 3. The 1H nmr spectra of tetrahydropyrimidines 1 are analyzed, discussing the influence of substituents in positions 1 and 2 of the heterocyclic ring. Alkaline hydrolysis of compounds 1, which originates exclusively N-acyl-N′-aryltrimethylenediamines

  描述了通过用多甲基三甲基甲硅烷基环化N-酰基-N'-芳基三亚甲基二胺2来合成1-芳基-2-烷基-1,4,5,6-四氢嘧啶1的通用方法。前体2通过相应的N-（3-溴丙基）酰胺3的氨解获得。分析了四氢嘧啶1的1 H nmr光谱，讨论了杂环1和2位上取代基的影响。化合物1的碱性水解，仅源于N-酰基-N'-芳基三亚甲基二胺2还通过中间体甲醇胺进行了研究。根据立体电子控制理论讨论了这种中间体的裂解。用硼烷还原化合物1会导致区域特异性地导致N-烷基-N'-芳基三亚甲基二胺6。
• A Convenient Synthesis of Unsymmetrical N,N′-Disubstitutedα,ω-Diaminoalkanes
  作者：Liliana R. Orelli、Alejandra Salerno、Mónica E. Hedrera、Isabel A. Perillo

  DOI：10.1080/00397919808006867

  日期：1998.5

  general procedure is described for regiospecific construction of unsymmetrical N-alkyl (or aralkyl)-N′-aryl-α,ω-diaminoalkanes 3 (n=2,3,4) by reduction of N-(ω -arylaminoalkyl)amides 2 with borane. Compounds 2 are readily obtained by condensation of N-(ω-haloalkyl)amides 1 with aromatic amines.

  摘要描述了通过还原 N-(ω-芳基氨基烷基)酰胺来区域特异性构建不对称 N-烷基 (或芳烷基)-N'-芳基-α,ω-二氨基烷烃 3 (n=2,3,4) 的一般程序2 与硼烷。化合物2很容易通过N-(ω-卤代烷基)酰胺1与芳香胺的缩合获得。
• E/Z equilibrium in tertiary amides. Part 2: N-acyl-N′-arylhexahydropyrimidines
  作者：Juan Á. Bisceglia、Ma. Cruz Mollo、Liliana R. Orelli

  DOI：10.1016/j.molstruc.2009.12.011

  日期：2010.3

  presented. Due to hindered rotation around the (O)C–N bond, tertiary amides 1 exist as a mixture of non-separable E/Z diastereoisomers, which show separate signals in the NMR spectra. For some selected derivatives, differential assignment of the 1 H resonances of the E/Z rotamers was made on the basis of the magnitude of ASIS (anisotropic solvent induced shifts) effects and confirmed by NOESY. The

  摘要 介绍了一系列新型 N-酰基-N ' - 芳基六氢嘧啶 1 的 1 H 和 13 C NMR 光谱研究。由于围绕 (O)C-N 键的旋转受阻，叔酰胺 1 以不可分离的 E/Z 非对映异构体的混合物形式存在，其在 NMR 光谱中显示出单独的信号。对于某些选定的衍生物，E/Z 旋转异构体的 1 H 共振的差异分配是根据 ASIS（各向异性溶剂引起的位移）效应的大小进行的，并由 NOESY 确认。HSQC 和 HMBC 实验明确地归因于相应的 13 C 信号。使用 ab initio RHF/6-311G++ 方法对两个代表性成员进行了详细的构象研究。
• 1,n-Diamines. Part 3: Microwave-assisted synthesis of N-acyl-N′-arylhexahydropyrimidines and hexahydro-1,3-diazepines
  作者：Juan Á. Bisceglia、Jimena E. Díaz、Romina A. Torres、Liliana R. Orelli

  DOI：10.1016/j.tetlet.2011.07.131

  日期：2011.10

  In this Letter we present a method for the synthesis of N-acyl-N'-arylhexahydropyrimidines 1, by ring closure of N-acyl-N'-aryl-1,3-propanediamines 3 with formaldehyde. Cyclodehydrations were performed in aqueous medium under microwave irradiation, and led to high yields of the desired compounds in remarkably short reaction times. The method also allowed for the synthesis of hitherto unreported N-acyl-N'-arylhexahydro-1,3-diazepines 2. The acyclic tetramethylenic precursors 4 were synthesized by selective functionalization of N-arylputrescines. (C) 2011 Elsevier Ltd. All rights reserved.
• Selective Monoformylation Of 1,3-Diaminopropane Derivatives
  作者：Liliana R. Orelli、María B. Garcia、Fernando Niemevz、Isabel A. Perillo

  DOI：10.1080/00397919908086172

  日期：1999.6

  A general procedure for regiospecific construction of N-aryl-N'-formyl-1,3-diaminopropanes 2 (R=H) by selective monoformylation of N-(3-aminopropyl)arylamines 1 is described. Compounds 1 are readily obtained with high yields by aminolysis of 3-bromopropylamine hydrobromide with aromatic amines. The present synthetic strategy was extended to the synthesis of other Nacyl-N'-aryl-1,3-diaminopropanes.