(E)-(3R,4aR,7S)-7-phenethyl-3-propenyl-hexahydropyrrolo[1,2-c]pyrimidin-1-ylideneamide hydrotrifluoromethanesulfonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (E)-(3R,4aR,7S)-7-phenethyl-3-propenyl-hexahydropyrrolo[1,2-c]pyrimidin-1-ylideneamide hydrotrifluoromethanesulfonate
• 英文别名: (3R,4aR,7S)-7-(2-phenylethyl)-3-[(E)-prop-1-enyl]-3,4,4a,5,6,7-hexahydro-2H-pyrrolo[1,2-c]pyrimidin-8-ium-1-amine;trifluoromethanesulfonate
• 化学式: CHF₃O₃S*C₁₈H₂₅N₃
• 分子量: 433.495
• InChiKey: ZBRXNDIISJRTQY-HNFWVIRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  顺-1,3-戊二烯 、 copper(II) bis(trifluoromethanesulfonate) 、 2-phenethyl-5-(phenylsulfanyl)pyrrolidine-1-carboximidamide hydrochloride 以 二氯甲烷 、 氯仿 为溶剂， 生成 (Z)-(3R,4aR,7R)-7-phenethyl-3-propenyl-hexahydropyrrolo[1,2-c]pyrimidin-1-ylideneamine hydrotrifluoroacetate 、 (E)-(3R,4aR,7S)-7-phenethyl-3-propenyl-hexahydropyrrolo[1,2-c]pyrimidin-1-ylideneamide hydrotrifluoromethanesulfonate
  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.