diphenyl-2,5-phospholyl-lithium | 115171-91-0

• 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: diphenyl-2,5-phospholyl-lithium
• 英文别名: lithium 2,5-diphenylphospholide；2,5-diphenylphospholyl lithium；2,5-diphenylphospholyllithium；Lithium;2,5-diphenyl-1-phosphanidacyclopenta-2,4-diene
• CAS: 115171-91-0
• 化学式: C₁₆H₁₂P*Li
• 分子量: 242.186
• InChiKey: OKLPCQSRELRICZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diphenyl-2,5-phospholyl-lithium 以10%的产率得到
  参考文献：
  名称：

  CHARRIER, C.;BONNARD, H.;DE, LAUZON, G.;MATHEY, F., J. AMER. CHEM. SOC., 1983, 105, N 23, 6871-6877

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,5-triphenyl-1H-phosphole 在 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 diphenyl-2,5-phospholyl-lithium
  参考文献：
  名称：

  Proton [1,5] shifts in P-unsubstituted 1H-phospholes. Synthesis and chemistry of 2H-phosphole dimers

  摘要：

  DOI：

  10.1021/ja00361a022

文献信息

• Reactivity of a 1,3,2-diazaphosphinine toward propargyl-phosphine derivatives and activated alkenes
  作者：Nicole Maigrot、Mohand Melaimi、Louis Ricard、Pascal Le Floch

  DOI：10.1002/hc.10152

  日期：——

  Reaction of 1 with 1-phenylpropargyl derivatives of diphenylphosphine 8 and phosphole 9 afforded 7,8-dihydro-1-phospha-2,6-diazabarrelenes 10 and 11 having an exocyclic double bond. Formation of these compounds results from a (1,3)-shift of a hydrogen atom from the methylene carbon atom to the bridge of the barrelene moiety. Depending on the nature of the phosphine group, the sulfur atom can also be displaced

  2,5-二苯基膦和 1-苯基炔丙基的二苯基膦衍生物 2, 3 通过将相应的二苯基膦锂和 2,5-二磷酰基锂盐与（3-溴-丙-1-炔基）-苯在 THF 中低温反应制备。然后在甲苯中在 90°C 下用元素硫对这些炔丙基衍生物进行硫化，得到相应的磷 8 和膦基 9 衍生物。3,5-二叔丁基-1,3,2-二氮杂膦 1 与游离磷衍生物的反应产生二氮杂膦 4 和 5 的混合物，在用过量的三甲基甲硅烷基乙炔处理后转化为相应的膦 6 和 7 . 1与二苯基膦8和磷酰基9的1-苯基炔丙基衍生物反应得到具有环外双键的7,8-二氢-1-磷杂-2,6-二氮杂二氮杂苯10和11。这些化合物的形成是由于氢原子从亚甲基碳原子到桶烯部分的桥的 (1,3) 位移。根据膦基团的性质，硫原子也可以被置换为桶烯部分的 P 原子。记录磷衍生物10的X射线结构。还通过 1 的反应合成了三个 6,7-dihydro-1-phospha-2
• Chiral rhodium complexes covalently anchored on carbon nanotubes for enantioselective hydrogenation
  作者：C. C. Gheorghiu、B. F. Machado、C. Salinas-Martínez de Lecea、M. Gouygou、M. C. Román-Martínez、P. Serp

  DOI：10.1039/c3dt53301h

  日期：——

  Chiral rhodium hybrid nanocatalysts have been prepared by covalent anchorage of pyrrolidine-based diphosphine ligands onto functionalized CNTs. This work constitutes the first attempt at covalent anchoring of homogeneous chiral catalysts on CNTs. The catalysts, prepared with two different chiral phosphines, were characterized by ICP, XPS, N2 adsorption and TEM, and have been tested in the asymmetric hydrogenation of two different substrates: methyl 2-acetamidoacrylate and α-acetamidocinnamic acid. The hybrid nanocatalysts have shown to be active and enantioselective in the hydrogenation of α-acetamidocinnamic acid. A good recyclability of the catalysts with low leaching and without loss of activity and enantioselectivity was observed.

  通过将吡咯烷基二膦配体共价锚定到功能化的 CNT 上，制备了手性铑杂化纳米催化剂。这项工作是在 CNT 上共价锚定均相手性催化剂的首次尝试。使用两种不同手性膦制备的催化剂通过 ICP、XPS、N2 吸附和 TEM 进行了表征，并在两种不同底物（2-乙酰氨基丙烯酸甲酯和 α-乙酰氨基肉桂酸）的不对称氢化中进行了测试。结果表明，混合纳米催化剂在 α-乙酰胺肉桂酸的氢化过程中具有活性和对映选择性。据观察，催化剂具有良好的可回收性，浸出率低，且不会丧失活性和对映体选择性。
• Characterisation of the parent phosphole and phospholyl anion and some of their C-substituted derivatives by 1H and 13C NMR spectroscopy
  作者：Claude Charrier、François Mathey

  DOI：10.1016/s0040-4039(00)96686-3

  日期：1987.1

  The parent phosphole and phospholyl anion as well as some C-substituted derivatives have been characterized by 1H and 13C NMR spectroscopy for the first time; the two most noteworthy features are the absence of 3J(-P-C-) couplings for the phospholes and the huge 1J(CP) couplings for the phospholyl anions.

  首次通过1 H和13 C NMR光谱对母体磷酸根和磷酸根阴离子以及一些C取代的衍生物进行了表征。两个最值得注意的特征是，没有3 J（-PC- ）偶联用于磷脂和巨大的1 J（CP）偶联用于磷酰基阴离子。
• Syntheses of a 2,6-bis-(methylphospholyl)pyridine ligand and its cationic Pd(II) and Ni(II) complexes – application in the palladium-catalyzed synthesis of arylboronic esters
  作者：Mohand Melaimi、Claire Thoumazet、Louis Ricard、Pascal Le Floch

  DOI：10.1016/j.jorganchem.2004.06.035

  日期：2004.9

  2,6-Bis(2,5-diphenylphospholyl-1-methyl)pyridine (2) was prepared from the reaction of 2,5-diphenylphospholide anion with 2,6-bis(chloromethyl)pyridine. The X-ray crystal structure of 2 was recorded. Reaction of 2 with [Pd(COD)Cl-2] in the presence of AgBF4 yields the cationic complex [Pd(2)Cl][BF4] (3). The analogous Ni complex [Ni(2)Br][BF4] (4) was prepared in a similar way by reacting ligand 2 with [NiBr2(DME)] in the presence of AgBF4 and its formulation was confirmed by an X-ray crystal structure study. Complex 3 efficiently catalyzes the coupling between pinacolborane and iodo and bromoarenes with good TON (up to 1 x 10(5) with iodo derivatives and 8.9 x 10(3) with bromo derivatives). (C) 2004 Elsevier B.V. All rights reserved.
• A Straightforward Synthesis of 3-Acylphospholes
  作者：Magali Clochard、Joanna Grundy、Bruno Donnadieu、François Mathey

  DOI：10.1021/ol051816d

  日期：2005.9.1

  graph The reaction of 2,5-diphenylphospholide, first with acyl chlorides, then with (BuOK)-Bu-t, provides a direct access to 3-acyl-2,5-diphenylphospholides via a 1H-, 2H-, 3H-phosphole equilibrium.