N-(4-chlorophenyl)tetramethylenediamine | 1245641-10-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-chlorophenyl)tetramethylenediamine
• 英文别名: N-(4-chlorophenyl)putrescine；N'-(4-chlorophenyl)butane-1,4-diamine
• CAS: 1245641-10-4
• 化学式: C₁₀H₁₅ClN₂
• 分子量: 198.695
• InChiKey: ZRYLVQOWOSLQEV-UHFFFAOYSA-N

物化性质

• 沸点：
  348.9±22.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)tetramethylenediamine 在 sodium carbonate 作用下， 以 水 为溶剂， 反应 0.03h， 生成 1-propionyl-3-(4-chlorophenyl)hexahydro-1,3-diazepine
  参考文献：
  名称：

  1,n-Diamines. Part 3: Microwave-assisted synthesis of N-acyl-N′-arylhexahydropyrimidines and hexahydro-1,3-diazepines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.07.131
• 作为产物：
  描述：

  4-chloro-N-(4-chlorophenyl)butyramide 在 sodium azide 、 diborane(6) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-(4-chlorophenyl)tetramethylenediamine
  参考文献：
  名称：

  N-取代的1，n-二胺的新合成路线。二。由ω-链烷酸衍生物合成选择性N-取代的四亚甲基和五亚甲基二胺

  摘要：

  描述了一种新的合成选择性N-取代的四亚甲基和五亚甲基二胺1（n  = 4,5）的方法。该方法使用N-取代的ω-卤代烷酰胺2作为前体，并涉及微波促进的转化成ω-叠氮羧酰胺3，然后用乙硼烷还原叠氮基和羧酰胺基团。

  DOI：

  10.1016/j.tetlet.2011.01.088

文献信息

• 1,n-Diamines. Part 2: Synthesis of acyclic and heterocyclic N-arylputrescine derivatives
  作者：Jimena E. Díaz、Juan Á. Bisceglia、Ma. Cruz Mollo、Liliana R. Orelli

  DOI：10.1016/j.tetlet.2011.02.042

  日期：2011.4

  and related seven-membered heterocyclic amidines 4. Compounds 1 were synthesized by Cs2CO3/KI-mediated aminolysis of 4-chlorobutyronitrile and subsequent reduction. N-Acylation of diamines 1 with carboxylic acid anhydrides led selectively to N-acyl-N′-aryl tetramethylenediamines 3. Microwave-assisted ring closure of such precursors promoted by PPE allowed for the synthesis of hitherto unreported 1-aryl-2-alkyl-1H-1

  在本函中，我们报道了使用N-芳基腐胺作为合成中间体，用于制备N-酰基-N'-芳基四亚甲基二胺3和相关的七元杂环am 4。通过Cs 2 CO 3 / KI介导的4-氯丁腈的氨解并随后还原来合成化合物1。二胺1与羧酸酐的N-酰化选择性地导致N-酰基-N'-芳基四亚甲基二胺3。由PPE促进的此类前体的微波辅助闭环反应允许合成迄今未报道的1-芳基-2-烷基-1 H -1,4,5,6-四氢-1,3-二氮杂4。
• New synthetic route for selectively substituted 1,n-diamines. Synthesis of N-aryl tetra- and pentamethylenediamines
  作者：María A. Ramirez、María V. Corona、Maria M. Blanco、Isabel A. Perillo、Williams Porcal、Alejandra Salerno

  DOI：10.1016/j.tetlet.2010.07.075

  日期：2010.9

  A general procedure for the synthesis of N-aryltetra- and pentamethylenediamines 1 by acid hydrolysis of N-aryl-N’-acylalkylenediamines 2 under microwave irradiation is described. The precursors 2 are obtained by amination of the corresponding N-(ω-haloalkyl)benzamides with aromatic amines 3.

  描述了通过在微波辐射下酸水解N-芳基-N'-酰基亚烷基二胺2来合成N-芳基四-和五亚甲基二胺1的一般程序。前体2通过将相应的N-（ω-卤代烷基）苯甲酰胺与芳族胺3胺化而获得。
• An Efficient Synthesis of<i>N</i>-Alkyl-<i>N</i>-arylputrescines and Cadaverines
  作者：María C. Mollo、Nadia Gruber、Jimena E. Díaz、Juan Á. Bisceglia、Liliana R. Orelli

  DOI：10.1080/00304948.2014.944404

  日期：2014.9.3
• New synthetic routes for N-substituted 1,n-diamines. II. Synthesis of selectively N-substituted tetra- and pentamethylenediamines from ω-alkanoic acid derivatives
  作者：María A. Ramírez、María V. Corona、Gisela Ortiz、Alejandra Salerno、Isabel A. Perillo、María M. Blanco

  DOI：10.1016/j.tetlet.2011.01.088

  日期：2011.3

  for the synthesis of selectively N-substituted tetra- and pentamethylenediamines 1 (n = 4,5) is described. The method uses N-substituted ω-haloalkanamides 2 as precursors and involves the microwave-promoted conversion into ω-azidocarboxamides 3 and later the reduction of both azido and carboxamide groups with diborane.

  描述了一种新的合成选择性N-取代的四亚甲基和五亚甲基二胺1（n  = 4,5）的方法。该方法使用N-取代的ω-卤代烷酰胺2作为前体，并涉及微波促进的转化成ω-叠氮羧酰胺3，然后用乙硼烷还原叠氮基和羧酰胺基团。
• 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.