8-(triphenylphosphoimino)quinoline | 377779-80-1

• 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: 8-(triphenylphosphoimino)quinoline
• 英文别名: 8-triphenylphosphoiminoquinoline；Ph3PN-8-C9H6N；8-[(Triphenyl-lambda~5~-phosphanylidene)amino]quinoline；triphenyl(quinolin-8-ylimino)-λ5-phosphane
• CAS: 377779-80-1
• 化学式: C₂₇H₂₁N₂P
• mdl: MFCD00482251
• 分子量: 404.451
• InChiKey: XZXPXSDTYYNSOE-UHFFFAOYSA-N

物化性质

• 沸点：
  587.3±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(triphenylphosphoimino)quinoline 在 CO 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 cis-triphenylphosphinimine(azidoquinoline) tetracarbonylmolybdenum(O)*monoacetonitrile
  参考文献：
  名称：

  Fourquet; Leblanc; Saravanamuthu, Inorganic Chemistry, 1991, vol. 30, # 17, p. 3241 - 3243

  摘要：

  DOI：
• 作为产物：
  描述：

  8-氨基喹啉 、 二溴三苯基膦 在 三乙胺 作用下， 以 苯 为溶剂， 以69%的产率得到8-(triphenylphosphoimino)quinoline
  参考文献：
  名称：

  Synthesis and Some Properties of Phosphoimino-1-azaazulene Derivatives

  摘要：

  3-Phenyl-8-triphenylphosphoimino- and 2-triphenylphosphoimino-1-azaazulenes were prepared by the reaction of the corresponding 8- and 2-amino-1-azaazulenes with triphenylphosphine dibromide. The structure of 3-phenyl-8-triphenylphosphoimino-1-azaazulene was investigated by X-Ray crystallographic analysis and molecular orbital calculation. The P-atom has trigonal bipiramidal coordination and the intramolecular distance between the N-1 and the P-atom is 2.762(6) Angstrom, the existence of an interaction between N-1 and the P-atom is considered.

  DOI：

  10.3987/com-01-9288

文献信息

• Cycloruthenated Complexes from Iminophosphoranes: Synthesis, Structure, and Reactivity with Internal Alkynes
  作者：David Aguilar、Raquel Bielsa、Tatiana Soler、Esteban P. Urriolabeitia

  DOI：10.1021/om100997x

  日期：2011.2.14

  Cycloruthenated complexes [(η6-arene)Ru(C6H4-2-PPh2═NR)Cl] (arene = benzene, p-cymene; R = Ph, H) containing orthometalated iminophosphoranes have been obtained by transmetalation reactions from Hg(C6H4-2-PPh2═NR)2 derivatives to [(η6-arene)Ru(μ-Cl)Cl]2. These complexes react cleanly with internal alkynes R1C≡CR2 (R1, R2 = Ph, Et, CO2Me), KPF6, and CuBr2, yielding the 1,1,2-triphenyl-3,4-di(alkyl/aryl)-2

  Cycloruthenated配合物[（η 6 -arene）的Ru（C 6 H ^ 4 -2-PPH 2 = NR）CL]（芳烃=苯，p ;含亚氨基正膦邻位已被从转移金属化反应得到-cymene R = PH，1H）汞柱（C 6 H ^ 4 -2-PPH 2 = NR）2个衍生物为[（η 6 -arene）的Ru（μ-Cl）的CL] 2。这些配合物反应干净地内炔[R 1 C≡CR 2（R 1，R 2 =苯基，等，CO 2 Me）时，KPF 6，和溴化亚铜2，得到1,1,2-三苯基-3,4-二（烷基/芳基）-2,1λ 5 -benzazaphosphinin -2-鎓杂环[C 6 H ^ 4 -PPh 2 -NPh-C（R 1）═ C（R 2 -3，4] +为PF 6盐。在所有研究的案例中，仅观察到单插入产物。在不对称炔烃MeC≡CPh的情况下，插入是区域选择性的，并且获得了[C 6 H 4
• Reactions of 8-(Triphenylphosphoimino)quinoline with Aryl Aldehydes and Aryl Isocyanates: Formation of 2-Aryl-4H-imidazo[4,5,1-ij]quinolines and Related Systems
  作者：Noritaka Abe、Kentaro Nagamatsu、Erina Akiyoshi、Hidenori Ito、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-06-s(o)6

  日期：——

  The reaction of 8-(triphenylphosphoimino)quinoline with aryl aldehydes gave 2-aryl-4H-imidazo[4,5,1-ij]quinolines. In the reaction, tandem aza-Wittig reaction and cyclization attended with hydride shift occurred. The reaction of 8-(triphenylphosphoimino)quinoline with aryl isocyanates gave 1,3-diaryl-1,2,3,9a-tetrahydro[1,3,5]triazolo[2',3':2,1;3',4'-a]imidazo[4,5,1-ij]quinolin-2-ones (11) and 2-(arylamino)imidazo[4

  8-(三苯基磷酸亚氨基)喹啉与芳基醛反应得到2-芳基-4H-咪唑并[4,5,1-ij]喹啉。在该反应中，发生了串联氮杂-维蒂希反应和伴随氢化物位移的环化反应。8-（三苯基磷酸亚氨基）喹啉与芳基异氰酸酯反应得到 1,3-二芳基-1,2,3,9a-四氢[1,3,5]三唑并[2',3':2,1;3', 4'-a]咪唑并[4,5,1-ij]quinolin-2-ones (11) 和 2-(arylamino)imidazo[4,5,1-ij]quinolin-4(4H)-ones (12) . 11a (Ar = Ph) 和 12a (Ar = Ph) 的结构通过 X 射线结构分析得到证实。
• In Vitro and in Vivo Evaluation of Water-Soluble Iminophosphorane Ruthenium(II) Compounds. A Potential Chemotherapeutic Agent for Triple Negative Breast Cancer
  作者：Malgorzata Frik、Alberto Martínez、Benelita T. Elie、Oscar Gonzalo、Daniel Ramírez de Mingo、Mercedes Sanaú、Roberto Sánchez-Delgado、Tanmoy Sadhukha、Swayam Prabha、Joe W. Ramos、Isabel Marzo、María Contel

  DOI：10.1021/jm5012337

  日期：2014.12.11

  A series of organometallic ruthenium(II) complexes containing iminophosphorane ligands have been synthesized and characterized. Cationic compounds with chloride as counterion are soluble in water (70-100 mg/mL). Most compounds (especially highly water-soluble 2) are more cytotoxic to a number of human cancer cell lines than cisplatin. Initial mechanistic studies indicate that the cell death type for these compounds is mainly through canonical or caspase-dependent apoptosis, nondependent on p53, and that the compounds do not interact with DNA or inhibit protease cathepsin B. In vivo experiments of 2 on MDA-MB-231 xenografts in NOD.CB17-Prkdc SCID/J mice showed an impressive tumor reduction (shrinkage) of 56% after 28 days of treatment (14 doses of 5 mg/kg every other day) with low systemic toxicity. Pharmacokinetic studies showed a quick absorption of 2 in plasma with preferential accumulation in the breast tumor tissues when compared to kidney and liver, which may explain its high efficacy in vivo.