N-(3-bromopropyl)propionamide | 178181-67-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3-bromopropyl)propionamide
• 英文别名: N-(3-bromopropyl)propanamide
• CAS: 178181-67-4
• 化学式: C₆H₁₂BrNO
• 分子量: 194.071
• InChiKey: HSVKZOYJFRZXEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)propionamide 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 N'-(4-chlorophenyl)-N-propylpropane-1,3-diamine
  参考文献：
  名称：

  不对称 N,N'-二取代α,ω-二氨基烷烃的简便合成

  摘要：

  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。

  DOI：

  10.1080/00397919808006867
• 作为产物：
  描述：

  丙酰氯 、 3-溴丙胺氢溴酸盐 生成 N-(3-bromopropyl)propionamide
  参考文献：
  名称：

  Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO

  摘要：

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.

  DOI：

  10.1021/jo050783c

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。
• Synthesis and Isolation of 5,6-Dihydro-4<i>H</i>-1,3-Oxazine Hydrobromides by Autocyclization of <i>N</i>-(3-Bromopropyl)amides
  作者：Damodara N. Reddy、Erode N. Prabhakaran

  DOI：10.1021/jo101955q

  日期：2011.1.21

  5,6-Dihydro-4H-1,3-oxazine hydrobromides have been synthesized by the nucleophilic autocyclo-O-alkylation of N-(3-bromopropyl)amides under neutral conditions in chloroform. It is found that electron-donating amide alpha-substituents influence the autocyclization efficiency.
• 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。
• Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO
  作者：Hatsuo Maeda、Hong-Yan Wu、Yuji Yamauchi、Hidenobu Ohmori

  DOI：10.1021/jo050783c

  日期：2005.10.1

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.