1,3-二(苯基)-1-(苯基氨基甲酰)脲 | 2645-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二(苯基)-1-(苯基氨基甲酰)脲
• 英文名称: N-hydroxy((phenylimino)methyl)-N,N'-diphenyl carbamimidic acid
• 英文别名: 1,3,5-Triphenylbiuret；1,3-diphenyl-1-(phenylcarbamoyl)urea
• CAS: 2645-39-8
• 化学式: C₂₀H₁₇N₃O₂
• 分子量: 331.374
• InChiKey: WGAZAGSSABJXDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二(苯基)-1-(苯基氨基甲酰)脲 在 三乙胺 、 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-Chloro-1,3,5-triphenyl-1,3,5-triaza-2λ3-phosphorinane-4,6-dione
  参考文献：
  名称：

  Mueller, Christian; Meyer, Thomas G.; Farkens, Michael, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 6, p. 760 - 766

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰酸苯酯 在 3,4-二甲氧基苯甲醛肟 、 三乙胺 作用下， 以 苯 为溶剂， 生成 1,3-二(苯基)-1-(苯基氨基甲酰)脲
  参考文献：
  名称：

  Abbaureaktionen 3- [2'-（（2″-二甲基氨基ä基）-苯基]-异苯并二氢呋喃† ‡

  摘要：

  3- [2'-（2'-二甲基氨基乙基）-苯基]-异色烷的降解

  DOI：

  10.1002/hlca.19760590327

文献信息

• Reaction of organozinc halides with aryl isocyanates
  作者：Haoran Yang、Danfeng Huang、Ke-Hu Wang、Changming Xu、Teng Niu、Yulai Hu

  DOI：10.1016/j.tet.2013.01.053

  日期：2013.3

  Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates

  Reformatsky试剂，苄基溴化锌或烷基碘化锌与芳基异氰酸酯直接反应，在温和的反应条件下产生相应的N-取代的氨基甲酸酯。然而，烯丙基溴化锌或炔丙基溴化锌与芳基异氰酸酯的反应产生相应的N-取代的酰胺。反应提供了合成N-取代的氨基甲酸酯或酰胺的替代方法。
• Synthesis and highly selective Diels–Alder cycloadditions of the new dienes N-substituted 2,3,5,6-tetrahydrobenzoxazol-2-ones
  作者：Rafael Martı́nez、Hugo A Jiménez-Vázquez、Francisco Delgado、Joaquı́n Tamariz

  DOI：10.1016/s0040-4020(02)01536-3

  日期：2003.1

  and the corresponding isocyanates 2a–2c. The presence of electron-donor substituents in the aryl ring of the isocyanate gave rise to the exclusive formation of the captodative olefins 10. Diene 8a proved to be reactive and stereoselective in Diels–Alder additions with a cyclic olefin. The reaction with acetylenic dienophiles yielded the 2,3-dihydrobenzoxazol-2-ones 21 and 24, as the products of sequential

  描述了一种新的二烯N-取代的2,3,4,5-四氢苯并恶唑-2-酮8a – 8c的合成，它是通过一步聚合从1,2-环己二酮（7a）和相应的异氰酸酯2a – 8c合成的。2c。在异氰酸酯的芳基环中电子给体取代基的存在引起排他性的Capdodative烯烃10的形成。事实证明，在Diels-Alder与环烯烃的加成反应中，二烯8a具有反应活性和立体选择性。与炔属二烯亲和物的反应产生2,3-二氢苯并恶唑-2-酮21和24，是顺序[4 + 2]环加成反应和Diels-Alder逆反应的产物。对甲基乙烯基酮（22）进行区域选择性和立体选择性串联Diels-Alder和Michael加成反应，制得螺旋桨29a。加合物19的中心双键的内在π-锥体化的证据将使29a形成中的exo立体选择合理化。这些反应中的区域选择性已根据FMO理论从头算得到了合理化。
• Mobilization of rat stomach ECL-cell histamine in response to short- or long-term treatment with omeprazole and/or YF 476 studied by gastric submucosal microdialysis in conscious rats
  作者：T Konagaya、M Bernsand、P Norlén、R Håkanson

  DOI：10.1038/sj.bjp.0704037

  日期：2001.5

  Mobilization of histamine from the ECL cells was monitored by gastric submucosal microdialysis in conscious rats. The ECL cells are known to operate under gastrin control and the purpose of the present study was to examine their in situ response to short‐term (12 h) as well as long‐term (28 days) hypergastrinaemia, induced by treatment with the proton pump inhibitor omeprazole. Hypergastrinaemia promptly raised the histamine concentration in the microdialysate. The effect was prevented by CCK2 receptor blockade (YF476). On day 7 of omeprazole treatment the microdialysate histamine concentration reached a peak, five times higher than before treatment. Subsequently (14 and 28 days), less histamine was mobilized. Gastrin infusion (4 h) raised the microdialysate histamine concentration in a dose‐dependent manner in fasted rats and freely fed rats and in rats treated with omeprazole for a week. However, while fasted and fed rats responded to low doses of gastrin, the omeprazole‐treated rats required large doses of gastrin to respond. When the amount of histamine mobilized was related to the serum gastrin concentration the following EC50 values could be calculated: fasted rats 2.3×10−10 M, freely fed rats 2.5×10−10 M, omeprazole‐treated rats 8.7×10−10 M. The maximal histamine responses in the three groups were 18.4 pmol 4 h−1±0.8, 21.9 pmol 4 h−1±1.2 and 68.0 pmol 4 h−1±3.5, respectively. The results suggest that ECL cells, exposed to a high gastrin concentration for a week, respond with a shift in the receptor‐ligand binding affinity from high to low. Apparently, CCK2 receptors of the ECL cells are subject to dynamic changes with respect to ligand‐binding affinity. British Journal of Pharmacology (2001) 133, 37–42; doi:10.1038/sj.bjp.0704037

  在清醒大鼠中，通过胃下黏膜微透析监测ECL细胞中组胺的释放。ECL细胞已知在促胃液素的调控下工作，本研究的目的是探讨它们对短期（12小时）和长期（28天）高促胃液素血症的< jats:italic>in situ反应，该高促胃液素血症通过质子泵抑制剂奥美拉唑的治疗诱导。高促胃液素血症迅速提高了微透析液中的组胺浓度。该效应被CCK2受体阻滞剂（YF476）所阻止。在奥美拉唑治疗的第7天，微透析液中的组胺浓度达到峰值，比治疗前高5倍。随后（14天和28天），释放的组胺减少。通过胃泌素输注（4小时）在禁食大鼠、自由摄食大鼠以及奥美拉唑治疗一周的大鼠中，微透析液中的组胺浓度呈现出剂量依赖性的上升。然而，禁食和自由摄食的大鼠对低剂量胃泌素有反应，而奥美拉唑治疗的大鼠则需要大剂量胃泌素才能产生反应。当释放的组胺量与血清胃泌素浓度相关时，可以计算出以下EC50值：禁食大鼠2.3×10−10 P，自由摄食大鼠2.5×10−10 P，奥美拉唑治疗的大鼠8.7×10−10 P。三个组的最大组胺反应分别为18.4 pmol 4 h-1 ±0.8、21.9 pmol 4 h-1 ±1.2和68.0 pmol 4 h-1 ±3.5。结果表明，暴露于高胃泌素浓度一周的ECL细胞，其受体-配体结合亲和力发生了从高到低的转变。显然，ECL细胞的CCK2受体在配体结合亲和力方面经历了动态变化。 英国药理学杂志（2001）133, 37–42；doi: 10.1038/sj.bjp.0704037
• Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C–H Amidation of 2-Phenylpyridine with Arylisocyanates
  作者：Alasdair I. McKay、Weam A. O. Altalhi、Lachlan E. McInnes、Milena L. Czyz、Allan J. Canty、Paul S. Donnelly、Richard A. J. O’Hair

  DOI：10.1021/acs.joc.9b02831

  日期：2020.2.21

  The Ru(II)-catalyzed amidation of 2-arylpyridines with aryl isocyanates via C-H bond activation is less efficient than described previously, due to the formation of a series of side products, which were readily identified using direct infusion electrospray mass spectrometry and high-performance liquid chromatography-mass spectrometry.

  由于形成了一系列副产物，这些副产物可以通过直接注入电喷雾质谱法和高效液相色谱法进行快速鉴定，因此，Ru（II）通过CH键活化将2-芳基吡啶与异氰酸芳基酯催化的酰胺化反应效率不如先前所述。高效液相色谱-质谱联用。
• One- or Two-Step Synthesis of C-8 and N-9 Substituted Purines
  作者：Mélanie Bollier、Frédérique Klupsch、Perrine Six、Laurent Dubuquoy、Nathalie Azaroual、Régis Millet、Natascha Leleu-Chavain

  DOI：10.1021/acs.joc.7b02269

  日期：2018.1.5

  A novel and original strategy to obtain rapidly a large diversity of C-8 and N-9 substituted purines was developed. The present procedure describes annulation reactions in one or two steps starting from 5-aminoimidazole-4-carbonitriles 1–8 in moderate to good yields. 8,9-Disubstituted-6,9-dihydro-1H-purin-6-ones 9–14, 6-amino-8,9-disubstituted-3,9-dihydro-2H-purin-2-ones 15–20, 8,9-disubstituted-3

  开发了一种新颖且新颖的策略来快速获得大量的C-8和N-9取代嘌呤。本过程描述在由5-氨基咪唑-4-甲腈开始一个或两个步骤的反应环1 - 8在中度至良好的产率。8,9-二取代-6,9-二氢ħ嘌呤-6-酮9 - 14，6-氨基-8,9-二取代的3,9-二氢-2- ħ -嘌呤-2-酮15 - 20，8,9-二取代的-3,9-二氢-2- ħ -嘌呤-2,6-二胺21 - 24和6-亚氨基-1-苯基-8,9-二取代的-6,9-二氢- 1 ħ -嘌呤-2-（3 H） -酮25 - 26分别在一个步骤中使用甲酸，脲，碳酸胍，和异氰酸苯酯分别合成，而8,9-二取代- 9 ħ嘌呤-6-胺27 - 31和6亚氨基-8， 9二取代的-6,9-二氢- 1 H ^ -嘌呤-1-胺32 - 33中使用甲酰胺和肼，分别两个步骤获得。