N-Benzyl-N'-benzoyl-guanidin | 18787-57-0

• 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-Benzyl-N'-benzoyl-guanidin
• 英文别名: N¹-Benzyl-N³-benzoyl-guanidin；N-(N'-benzylcarbamimidoyl)benzamide
• CAS: 18787-57-0
• 化学式: C₁₅H₁₅N₃O
• 分子量: 253.304
• InChiKey: LKUIKHYCBHPKEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C(Solv: carbon tetrachloride (56-23-5))
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N'-benzoyl-guanidin 在 碘苯二乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以63%的产率得到N-Benzyl-5-phenyl-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  的3-氨基-5-芳基-1,2,4-恶二唑简便合成经由PIDA介导的分子内氧化环化†

  摘要：

  开发了一种温和有效的方法，以PhI（OAc）2（PIDA）为氧化剂，通过分子内环化合成3-氨基-5-芳基-1,2,4-恶二唑。以中等到良好的产率制备了各种3-氨基-5-芳基-1,2,4-恶二唑，并提出了由PIDA介导的N–O键形成机理。鉴于容易获得的起始原料，操作简便，高功能耐受性和低毒性，该方案为1,2,4-恶二唑提供了一种新颖的合成策略。

  DOI：

  10.1039/c6ra08871f
• 作为产物：
  描述：

  N-苯甲酰基-N'-苄基硫脲 在 叔丁基过氧化氢 、 氨 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 96.0h， 以22%的产率得到N-Benzyl-N'-benzoyl-guanidin
  参考文献：
  名称：

  A simple one-pot methodology for the synthesis of substituted benzoylguanidines from benzoylthioureas using tert-butyl hydroperoxide

  摘要：

  The potential of tert-butyl hydroperoxide as a reagent in the guanylation of benzoylthioureas in the presence of amines has been evaluated in a systematic study involving substrates bearing N-2-substituents with different electronic properties. The results show that (BuOOH)-Bu-t is a suitable and robust reagent for the synthesis of either N-1,N-2,N-3-tri- and tetrasubstituted or N-1,N-2-disubstituted guanidines from N-2-substituted N-1-benzoylthioureas and N-1-benzoylthioureas, respectively. The recrystallised guanylation adducts were readily obtained in good yields and at high purity levels after a simple one-pot reaction procedure. The crystal structures of two novel benzoylguanidines are provided. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.088

文献信息

• Solid-phase synthesis of N , N ′-substituted acylguanidines
  作者：Dharmpal S Dodd、Yufen Zhao

  DOI：10.1016/s0040-4039(00)02265-6

  日期：2001.2

  An efficient method for the solid-phase synthesis of N,N′-substituted acylguanidines is presented. The key-step involves the N-acylation of resin immobilized S-methylisothiourea with a variety of carboxylic acids using PyAOP as the coupling agent. The resulting resin bound N-acyl-derivatives are reacted with a host of amines and the N-acyl,N′-alkyl(aryl)guanidines liberated from the resin upon exposure

  提出了一种固相合成N，N'-取代的酰基胍的有效方法。的关键步骤涉及Ñ树脂的酰化固定小号-methylisothiourea与各种使用PyAOP作为偶联剂羧酸。使所得树脂结合的N-酰基衍生物与大量胺反应，并在暴露于TFA时从树脂中释放出N-酰基，N'-烷基（芳基）胍。
• An eco-friendly protocol for synthesis of thiourea derivatives: 1-benzoyl-3-benzylguanidine and 1-benzoyl-3-benzyl-O-ethylisourea. A possible non-purely thermal microwave assisted reaction
  作者：Heiddy Marquez、André Loupy、Osmar Calderon、Eduardo R. Pérez

  DOI：10.1016/j.tet.2005.12.037

  日期：2006.3

  nucleophilic amines promoted the sulfur elimination by attack on the thiocarbonyl group in both thiourea and thiocarbamates to afford guanidines and isourea, respectively. Transesterification products were obtained from p-TsOH catalyzed reaction of thiocarbamate with alcohols under MW-solvent-free conditions. Very important non-purely thermal MW specific effects were evidenced and attributed to stabilization

  使用KF在干燥介质条件下从1-苯甲酰基-3-苄基硫脲和苯甲酰基-乙基硫代氨基甲酸酯以良好的收率（分别为68％和76％）合成了1-苯甲酰基-3-苄基胍和1-苯甲酰基-3-苄基-O-乙基异脲–微波辐射下的Al 2 O 3。强亲核胺通过攻击硫脲和硫代氨基甲酸酯中的硫代羰基而促进了硫的消除，从而分别提供了胍和异脲。酯交换产物是在无MW溶剂的条件下，由对氨基甲酸酯与硫醇的对-TsOH催化反应制得的。证明了非常重要的非纯热MW特有效应，并归因于物质与波浪之间的库仑相互作用而稳定。
• Iodine-Mediated Multi-Component Reactions: Readily Access to Tetrazoles and Guanidines
  作者：Bajivali Shaik、Mohan Seelam、Ramana Tamminana、Prasad Rao Kammela

  DOI：10.2174/1570178617999200728212116

  日期：2021.5

  Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored.

  摘要：苯甲酰氯与胺的一锅式顺序反应，随后在碱性条件下处理分子I2试剂，以中等至优良的产率提供苯甲酰四唑和胍胺。这种一锅式合成具有多个优点，如温和的反应条件、短的反应时间、方便的处理、高产率，使用廉价且易获得的试剂分子碘。此外，功能团容忍性已经得到探索。
• Facile synthesis of 3-amino-5-aryl-1,2,4-oxadiazoles via PIDA-mediated intramolecular oxidative cyclization
  作者：Kuan Lu、Liancheng Duan、Boxuan Xu、Weile Yin、Di Wu、Yanfang Zhao、Ping Gong

  DOI：10.1039/c6ra08871f

  日期：——

  A mild and efficient method for the synthesis of 3-amino-5-aryl-1,2,4-oxadiazole by intramolecular cyclization using PhI(OAc)2 (PIDA) as an oxidant is developed. Various 3-amino-5-aryl-1,2,4-oxadiazoles are prepared in moderate to good yields, and the PIDA-mediated N–O bond formation mechanism is suggested. In view of the readily available starting materials, operational simplicity, high functionality

  开发了一种温和有效的方法，以PhI（OAc）2（PIDA）为氧化剂，通过分子内环化合成3-氨基-5-芳基-1,2,4-恶二唑。以中等到良好的产率制备了各种3-氨基-5-芳基-1,2,4-恶二唑，并提出了由PIDA介导的N–O键形成机理。鉴于容易获得的起始原料，操作简便，高功能耐受性和低毒性，该方案为1,2,4-恶二唑提供了一种新颖的合成策略。
• A simple one-pot methodology for the synthesis of substituted benzoylguanidines from benzoylthioureas using tert-butyl hydroperoxide
  作者：Henrique Esteves、Ângelo de Fátima、Rosane de P. Castro、José R. Sabino、Fernando Macedo、Tiago Oliveira Brito

  DOI：10.1016/j.tetlet.2015.10.088

  日期：2015.12

  The potential of tert-butyl hydroperoxide as a reagent in the guanylation of benzoylthioureas in the presence of amines has been evaluated in a systematic study involving substrates bearing N-2-substituents with different electronic properties. The results show that (BuOOH)-Bu-t is a suitable and robust reagent for the synthesis of either N-1,N-2,N-3-tri- and tetrasubstituted or N-1,N-2-disubstituted guanidines from N-2-substituted N-1-benzoylthioureas and N-1-benzoylthioureas, respectively. The recrystallised guanylation adducts were readily obtained in good yields and at high purity levels after a simple one-pot reaction procedure. The crystal structures of two novel benzoylguanidines are provided. (C) 2015 Elsevier Ltd. All rights reserved.