N,N'-bis(tert-butoxycarbonyl)-N''-{1-[2-(1,3-dioxolan-2-yl)ethyl]-3-phenylpropyl}guanidine | 346423-25-4

• 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'-bis(tert-butoxycarbonyl)-N''-{1-[2-(1,3-dioxolan-2-yl)ethyl]-3-phenylpropyl}guanidine
• 英文别名: tert-butyl N-[N'-[1-(1,3-dioxolan-2-yl)-5-phenylpentan-3-yl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 346423-25-4
• 化学式: C₂₅H₃₉N₃O₆
• 分子量: 477.601
• InChiKey: PSDSTEFKDJZVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 三氟乙酸 、 N,N'-bis(tert-butoxycarbonyl)-N''-{1-[2-(1,3-dioxolan-2-yl)ethyl]-3-phenylpropyl}guanidine 以 二氯甲烷 为溶剂， 反应 17.0h， 以73%的产率得到2-phenethyl-5-(phenylsulfanyl)pyrrolidine-1-carbimidamide hydrotrifluoroacetate
  参考文献：
  名称：

  Synthesis of Polycyclic Guanidines by Cyclocondensation Reactions of N-Amidinyliminium Ions

  摘要：

  A new method for the synthesis of polycyclic guanidines is described. The N-amidinyliminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergoes cyclocondensation with 1,3-dienes, styrenes, and beta -dicarbonyl compounds to give 1-iminohexahydropyrrolo[1,2-c]pyrimidines having side chains at C3 and C7. In all cases, major products have a cis relationship of the C7 side chain and angular C4a hydrogen, whereas C3 side chains are incorporated with lower stereoselectivity (dr = 2-5:1) in cyclocondensations with dienes and styrenes to give stereoisomer 39 as the major product.. In contrast to most cycloadditions of alkenes with N-acyliminium ions, cyclocondensations of alkenes with N-amidinyliminium ions proceed by a stepwise pathway. Cyclocondensation of the cognate ureido aminal 31 with styrene provides the rare 2-imino-5,6-dihydro-4H-1,3-oxazine derivative 32, rather than a pyrimidine as the major product. The high stereoselectivity observed in condensations of 16 with benzyl acetoacetate to afford Biginelli adduct 29 supports the intermediacy of N-amidinyliminium ions in related tethered Biginelli condensations of guanidines reported earlier from our laboratories.

  DOI：

  10.1021/jo0100998
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 在 lithium aluminium tetrahydride 、 三(2-氯乙基)胺 、 2-氯-1-甲基吡啶碘化物 、 碘 、 magnesium 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 21.33h， 生成 N,N'-bis(tert-butoxycarbonyl)-N''-{1-[2-(1,3-dioxolan-2-yl)ethyl]-3-phenylpropyl}guanidine
  参考文献：
  名称：

  Synthesis of Polycyclic Guanidines by Cyclocondensation Reactions of N-Amidinyliminium Ions

  摘要：

  A new method for the synthesis of polycyclic guanidines is described. The N-amidinyliminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergoes cyclocondensation with 1,3-dienes, styrenes, and beta -dicarbonyl compounds to give 1-iminohexahydropyrrolo[1,2-c]pyrimidines having side chains at C3 and C7. In all cases, major products have a cis relationship of the C7 side chain and angular C4a hydrogen, whereas C3 side chains are incorporated with lower stereoselectivity (dr = 2-5:1) in cyclocondensations with dienes and styrenes to give stereoisomer 39 as the major product.. In contrast to most cycloadditions of alkenes with N-acyliminium ions, cyclocondensations of alkenes with N-amidinyliminium ions proceed by a stepwise pathway. Cyclocondensation of the cognate ureido aminal 31 with styrene provides the rare 2-imino-5,6-dihydro-4H-1,3-oxazine derivative 32, rather than a pyrimidine as the major product. The high stereoselectivity observed in condensations of 16 with benzyl acetoacetate to afford Biginelli adduct 29 supports the intermediacy of N-amidinyliminium ions in related tethered Biginelli condensations of guanidines reported earlier from our laboratories.

  DOI：

  10.1021/jo0100998

文献信息

• Synthesis of Polycyclic Guanidines by Cyclocondensation Reactions of <i>N</i>-Amidinyliminium Ions
  作者：Larry E. Overman、John P. Wolfe

  DOI：10.1021/jo0100998

  日期：2001.5.1

  A new method for the synthesis of polycyclic guanidines is described. The N-amidinyliminium ion generated from alpha-(phenylthio)amidine precursor 16 by reaction with Cu(OTf)(2) undergoes cyclocondensation with 1,3-dienes, styrenes, and beta -dicarbonyl compounds to give 1-iminohexahydropyrrolo[1,2-c]pyrimidines having side chains at C3 and C7. In all cases, major products have a cis relationship of the C7 side chain and angular C4a hydrogen, whereas C3 side chains are incorporated with lower stereoselectivity (dr = 2-5:1) in cyclocondensations with dienes and styrenes to give stereoisomer 39 as the major product.. In contrast to most cycloadditions of alkenes with N-acyliminium ions, cyclocondensations of alkenes with N-amidinyliminium ions proceed by a stepwise pathway. Cyclocondensation of the cognate ureido aminal 31 with styrene provides the rare 2-imino-5,6-dihydro-4H-1,3-oxazine derivative 32, rather than a pyrimidine as the major product. The high stereoselectivity observed in condensations of 16 with benzyl acetoacetate to afford Biginelli adduct 29 supports the intermediacy of N-amidinyliminium ions in related tethered Biginelli condensations of guanidines reported earlier from our laboratories.