bis(1-methylimidazol-2-yl)phenyl phosphine | 150404-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: bis(1-methylimidazol-2-yl)phenyl phosphine
• 英文别名: bis(1-methylimidazol-2-yl)phenylphosphane；bis(1-methylimidazol-2-yl)phenylphosphine；2-BIP(NMe)；1-methyl-2-[(1-methyl-1H-imidazol-2-yl)(phenyl)phosphanyl]-1H-imidazole；bis(1-methylimidazol-2-yl)-phenylphosphane
• CAS: 150404-20-9
• 化学式: C₁₄H₁₅N₄P
• 分子量: 270.274
• InChiKey: VRNPPFDUZZHKAO-UHFFFAOYSA-N

物化性质

• 沸点：
  472.4±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(1-methylimidazol-2-yl)phenyl phosphine 在 selenium 作用下， 反应 16.0h， 生成 bis(1-methyl-1H-imidazol-2-yl)(phenyl)phosphine selenide
  参考文献：
  名称：

  1JPSe耦合常数是膦碱度的可靠探针吗？A31P 核磁共振研究

  摘要：

  摘要 不同的杂芳基和官能化芳基取代基对杂芳基膦和二膦中磷原子的给电子能力和碱性的影响已通过使用相应硒化物的直接 1JPSe 偶联常数确定。讨论了使用 31P-77Se 自旋-自旋耦合常数作为膦碱度的探针的一般性以及该概念的范围和限制。图形概要

  DOI：

  10.1080/10426507.2010.547892
• 作为产物：
  描述：

  N-甲基咪唑 、 苯基二氯化磷 在 吡啶 、 三乙胺 作用下， 生成 bis(1-methylimidazol-2-yl)phenyl phosphine
  参考文献：
  名称：

  1-甲基咪唑基膦配体在钯催化的Suzuki偶联反应中的催化活性

  摘要：

  使用PdCl 2作为催化剂测试了三个基于N-甲基咪唑的膦配体在Suzuki偶联反应中的催化活性。结果表明，所有三种膦配体均对铃木反应表现出优异的活性，并且随着咪唑基团数量的增加，催化活性降低。版权所有©2014 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.3249

文献信息

• Ruthenium piano-stool complexes bearing imidazole-based PN ligands
  作者：Peter C. Kunz、Indre Thiel、Anna Louisa Noffke、Guido J. Reiß、Fabian Mohr、Bernhard Spingler

  DOI：10.1016/j.jorganchem.2011.10.006

  日期：2012.1

  cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes [CpRu(C10H8)]PF6, [CpRu(NCMe)3]PF6 and [CpRu(PPh3)2Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were κ1P-monodentate, κ2P,N-, κ2N,N-

  从前体复合物[CpRu（C 10 H 8）] PF 6，[CpRu（NCMe）3 ] PF 6和[ CpRu（PPh 3）2 Cl]。所用的PN配体是咪唑-2-基，-4-基和-5-基膦。 取决于配体和前体，观察到不同类型的配位模式。在polyimidazolyl PN的情况下配体这些都是κ 1个P -monodentate，κ 2 P，N - ，κ 2 N，N- -和κ 3 N，N，N- -螯合剂和μ-κ P：κ 2 N，N-桥接。的固态结构[CPRU（1A）2 CL]·H 2 O（5 。 ħ 2 O）和[CPRU（μ-κ 2 -N，N- κ ' 1 -P -图2b）} 2 ] （C 6H 5 PO 3 H）2（C 6 H 5 PO 3 H 2）2也是确定的[CpRu（2b）} 2 ]（PF 6）2的水解产物。2CH 3 CN（7b中。 2CH 3 CN）进行了测定（1A  =咪唑-2-
• C-Phosphorylation of Azoles with Trivalent Phosphorus Halides
  作者：Alexander M. Pinchuk、Andrew A. Tolmachev、Alexander N. Kostyuk、Alexander A. Yurchenko、Angelika I. Sviridon

  DOI：10.1080/10426509608545194

  日期：1996.1

  Abstract Simple method of C-phosphorylation of azoles by trivalent phosphorus halides in the pyridine solution have been developed. Hetaryldihalogen, dihetarylhalogen-, trihetarylphosphines, which were transformed into new types of P(III) and P(IV) derivatives, have been synthesized. Features of their reaction ability stipulated by the influence of hetaryl residues are found.

  摘要 开发了三价卤化磷在吡啶溶液中C-磷酸化唑类的简单方法。Hetaryldihalogen、dihetarylhalogen-、trihetarylphosphines 已被合成，它们被转化为新型的 P(III) 和 P(IV) 衍生物。发现了由杂芳基残基的影响规定的它们的反应能力的特征。
• Imidazole-based phosphane gold(I) complexes as potential agents for cancer treatment: Synthesis, structural studies and antitumour activity
  作者：Peter C. Kunz、Matthias U. Kassack、Alexandra Hamacher、Bernhard Spingler

  DOI：10.1039/b902748c

  日期：——

  The reaction of the imidazolyl-4(5)-phosphane ligands 2-isopropylimidazol-4(5)yl-diphenylphosphane (4-MIPiPr) and tris(2-isopropylimidazol-4(5)yl)phosphane (4-TIPiPr) towards gold(I) has been explored and compared to those of analogous 1-methylimidazol-2-ylphosphane ligands. The structure of [(4-MIPiPr)AuCl] (4) shows a linear P–Au–Cl coordination, whereas the 4-TIPiPr ligand forms a dinuclear complex [(4-TIPiPr)Au}2]Cl2 (5). Here, 4-TIPiPr bridges two gold(I) atoms in a head-to-tail P,N fashion. Complex 5 forms in the presence of the hard Lewis acid ZnCl2 the bimetallic complex [AuCl(4-TIPiPr)ZnCl]Cl (6), in which 4-TIPiPr bridges the two metal centers. In accordance with the HSAB concept the Au(I) atom is coordinated by the P atom and the zinc(II) by three N atoms in a N,N,N fashion. The solid-state structures of the complexes 4–6 have been elucidated by single-crystal X-ray analysis. The Au(I)–Au(I) contact in 5 is 2.8821(15) Å. The biological activities of all imidazol-2-yl- and imidazol-4(5)-ylphosphane gold(I) complexes towards nine human cancer cell lines including seven ovarian cancer cell lines of different sensitivity towards cisplatin and two leukemia cell lines have been explored.

  咪唑基-4(5)-膦配体2-异丙基咪唑-4(5)基-二苯基膦(4-MIPiPr)和三(2-异丙基咪唑-4(5)基)膦(4-TIPiPr)对金的反应(I) 已被探索并与类似的 1-甲基咪唑-2-基膦配体进行比较。 [(4-MIPiPr)AuCl] (4) 的结构显示出线性 P-Au-Cl 配位，而 4-TIPiPr 配体形成双核配合物 [(4-TIPiPr)Au}2]Cl2 (5)。此处，4-TIPiPr 以头尾相连的 P,N 方式桥接两个金 (I) 原子。配合物 5 在硬路易斯酸 ZnCl2 存在下形成双金属配合物 [AuCl(4-TIPiPr)ZnCl]Cl (6)，其中 4-TIPiPr 桥接两个金属中心。根据 HSAB 概念，Au(I) 原子由 P 原子配位，锌(II) 原子由三个 N 原子以 N、N、N 方式配位。配合物 4-6 的固态结构已通过单晶 X 射线分析阐明。 5 中的 Au(I)-Au(I) 接触面积为 2.8821(15) Å。已探索所有咪唑-2-基-和咪唑-4(5)-基膦金(I)复合物对九种人类癌细胞系（包括七种对顺铂具有不同敏感性的卵巢癌细胞系和两种白血病细胞系）的生物活性。
• Cytotoxicity of ruthenium(II) piano-stool complexes with imidazole-based PN ligands
  作者：Wilhelm Huber、Philip Bröhler、Wim Wätjen、Walter Frank、Bernhard Spingler、Peter C. Kunz

  DOI：10.1016/j.jorganchem.2012.06.027

  日期：2012.10

  A series of p-cymene ruthenium(II) complexes with imidazol-2-yl phosphines as PN ligands was prepared. Depending on the number of imidazolyl substituents in the ligands Ph3-nP(im)(n) 1-3: n = 1-3, im imidazol-2-yl (a), 1-methylimidazol-2-yl (b)} different coordination modes were observed: kappa P, kappa N-2,N or kappa N-3,N,N. The complexes were tested for their cytotoxicity in different cancer cell lines. Most of the compounds were found to be non-toxic; The compounds [(p-cymene)Ru(1a)Cl-2] (4a) shows cytotoxicity towards A2780sens and Hct116 cells in the mM range but not in H4IIE cells. The cytotoxicity is decreased upon introduction of a methyl group as [(p-cymene)Ru(1b)Cl-2] (4b) shows only modest toxicities in the cell lines investigated. The kappa P compound [(p-cymene)Ru(2a)Cl-2] (5a) shows selective toxicity in H4IIE cells after 72 h whereas the kappa N-2, N compound [(p-cymene)Ru(2a) Cl] OTf (5a') showed no toxicity in the cell lines investigated which again. (C) 2012 Elsevier B. V. All rights reserved.
• Tolmachev, A. A.; Yurchenko, A. A.; Semenova, M. G., Russian Journal of General Chemistry, 1993, vol. 63, # 3.2, p. 504 - 506
  作者：Tolmachev, A. A.、Yurchenko, A. A.、Semenova, M. G.、Feshchenko, N. G.

  DOI：——

  日期：——