5-(diphenylphosphino)uracil | 89029-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(diphenylphosphino)uracil
• 英文别名: 5-Diphenylphosphino-uracil；5-diphenylphosphine-uracil；PPh2Ur；5-(Diphenylphosphanyl)pyrimidine-2,4(1H,3H)-dione；5-diphenylphosphanyl-1H-pyrimidine-2,4-dione
• CAS: 89029-29-8
• 化学式: C₁₆H₁₃N₂O₂P
• 分子量: 296.265
• InChiKey: HDPFOXHLJJFZAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(diphenylphosphino)uracil 在 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到5-diphenylphosphoryl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and coordination chemistry of pyrimidine-substituted phosphine ligands

  摘要：

  Reaction of PPh2H with UrI (Ur = uracil) in the presence of Pd(OAc)(2) affords PPh(2)Ur. In the solid state, PPh(2)Ur crystallises as a methanol solvate in the monoclinic space group P2(1)/c. Reaction of PPh(2)Ur with CuI in dry and deoxygenated THF solution results in the formation of [Cu-4(mu(3)-I)(4)(PPh(2)Ur)(4)]. A single crystal X-ray diffraction study demonstrated that this species contains a distorted tetrahedral core of copper atoms, with facially-capping iodides. The uracil groups in the clusters are engaged in hydrogen bonding to groups on neighbouring molecules to form an extended array. A similar reaction between PPh(2)Ur and CuI in unpurified THF allows for the isolation of the phosphine oxide P(O)PPh(2)Ur. The synthesis of the benzyl-protected phosphine PPh(2)Ur(P) is also described [Ur(P) = 2,4-bis(benzyloxy)pyrimidine]. Reaction of PPh(2)Ur(P) with [Ru(eta(5)-C5H5)(NCMe)(3)]PF6 allows for isolation of [Ru(eta(5)-C5H5)(NCMe)(PPh(2)Ur(P))(2)]PF6. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.10.058
• 作为产物：
  描述：

  5-diphenylphosphanyl-1H-pyrimidine-2,4-dione;ethanol 生成 5-(diphenylphosphino)uracil
  参考文献：
  名称：

  ELLERMANN, J.;DEMUTH, A. A. M., Z. NATURFORSCH., 1983, 38, N 10, 1165-1172

  摘要：

  DOI：

文献信息

• Chemie polyfunktioneller Moleküle, 74 [1]. Synthese, Umlagerung und Eigenschaften diphenylphosphinosubstituierter Uracile / Chemistry of Polyfunctional Molecules, 74 [1]. Synthesis, Rearrangement and Properties of Diphenylphosphino Substituted Uracils
  作者：Jochen Ellermann、Alfons A. M. Demuth

  DOI：10.1515/znb-1983-1002

  日期：1983.10.1

  5-Bromo-uracil (2) with chloro-diphenylphosphine and triethylamine gives 5-bromo-N(1),N(3)-bis(diphenylphosphino)-uracil (3). In moist acetone, 3 is hydrolyzed to 5-bromo-N(1)-diphenylphosphino-uracil (4). 3 reacts with n-butyllithium under rearrangement and, with HCl, under elimination of a PPh₂-group, forms C(5)-diphenylphosphino-uracil (7a). Recrystallization of 7 a from ethanol yields the ethanol-1:1-adduct 7b. Heating of 7a in dimethylsulfoxide with D₂O yields the N(1),N(3)-dideutero-C(5)-diphenylphosphino-uracil (7c). All compounds were characterized by infrared, Raman, ¹H, ³¹P NMR and mass spectra. 7a shows a very small antitumor activity.

  5-溴尿嘧啶(2)与氯代二苯基膦和三乙胺反应，得到5-溴-N(1)，N(3)-双(二苯基膦基)-尿嘧啶(3)。在湿润的丙酮中，3被水解为5-溴-N(1)-二苯基膦基-尿嘧啶(4)。3与正丁基锂反应并重排，在HCl的作用下，消除了一个PPh₂基团，形成C(5)-二苯基膦基-尿嘧啶(7a)。从乙醇中结晶出7a的乙醇-1:1加合物7b。在二甲基亚砜中加热7a和D₂O，得到N(1)，N(3)-二氘-C(5)-二苯基膦基-尿嘧啶(7c)。所有化合物都通过红外、拉曼、¹H、³¹P NMR和质谱进行了表征。7a显示出非常小的抗肿瘤活性。

• Self-assembly of a hydrogen bonded framework from a gold phosphine complex with a pendant uracil group
  作者：Tracy D. Nixon、Lee D. Dingwall、Jason M. Lynam、Adrian C. Whitwood

  DOI：10.1039/b821671a

  日期：——

  The easily prepared complex AuCl(PPh2Ur) (Ur = uracil) self-assembles in the solid state to form crystals containing solvent-accessible channels, the structure remains crystalline even after removal and re-addition of solvent.

  易于制备的复合物 AuCl(PPh2Ur)（Ur = 尿嘧啶）可在固态下自组装形成含有溶剂通道的晶体，即使在移除溶剂并重新加入溶剂后，该结构仍保持结晶状态。
• Chemie polyfunktioneller moleküle
  作者：Jochen Ellermann、Eberhard Köck、Helmuth Zimmermann、Martin Gomm

  DOI：10.1016/0022-328x(88)80245-6

  日期：1988.5

  The compound dicarbonylnitrosyl-(5-diphenylphosphino-uracil)cobalt(−I)· methanol() was prepared by the reaction of Co(NO)(CO)3 with 5-(diphenylphosphino)uracil in tetrahydrofuran and recrystallized from methanol. The complex was identified from its 1H NMR, IR, and mass spectra, and studied by X-ray crystallography. It crystallizes in the monoclinic space group P21/n with a 8.755(1), b 16.549(8), c

  通过使Co（NO）（CO）3与5-（二苯基膦基）尿嘧啶在四氢呋喃中反应并从甲醇中重结晶来制备化合物二羰基亚硝酰基-（5-二苯基膦基-尿嘧啶）钴（-1）·甲醇（）。从其1 H NMR，IR和质谱鉴定该配合物，并通过X射线晶体学对其进行研究。该晶体的斜空间群中P 2 1 / Ñ与一个8.755（1），b 16.549（8），Ç 16.319（3）α，β91.97（2）°和Ž = 4。struture被提炼的基础上的3504 Reflectionios转换为R= 0.059。Co原子以稍微扭曲的四面体几何形状四配位。5-（二苯基膦基）尿嘧啶配体通过P原子配位。一个NO和两个CO基团占据了其他三个位置。CoP，CoNO和两个CoCo距离分别为2.231（1），1.641（3），1.755（3）和1.774（3）Å。在晶体中，甲醇分子通过氢键沿a轴以一维排列连接尿嘧啶部分。