bis(trimethylsilyl)phenylphosphine | 24103-44-4

• 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: bis(trimethylsilyl)phenylphosphine
• 英文别名: Phenylbis(trimethylsilyl)phosphan；Phenylbis(trimethylsilyl)phosphin；phenylbis(trimethylsilyl)phosphane；phenylbis(trimethylsilyl)phosphine；Phenylbis(tri-methylsilyl)phosphine；phenyl-bis(trimethylsilyl)phosphane
• CAS: 24103-44-4
• 化学式: C₁₂H₂₃PSi₂
• 分子量: 254.459
• InChiKey: GVEYKVGCJIJGIW-UHFFFAOYSA-N

物化性质

• 沸点：
  103-105 °C(Press: 1.0 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  bis(trimethylsilyl)phenylphosphine 在 乙醇锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 220.0h， 生成
  参考文献：
  名称：

  化学平衡中的三苯基磷烯烃

  摘要：

  在 PhP(Li)TMS 与具有不同对位取代基的二苯甲酮之间的改性磷-彼得森反应中，三苯基磷烯烃 1a-c 以良好至优异的产率制备。

  DOI：

  10.1002/ejic.201801322
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 苯基膦 在 三乙胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.17h， 生成 bis(trimethylsilyl)phenylphosphine
  参考文献：
  名称：

  Dithieno[3,2-c:2′,3′-e]-2,7-diketophosphepin: A Unique Building Block for Multifunctional π-Conjugated Materials

  摘要：

  A series of conjugated materials based on the new dithieno[3,2-c:2',3'-e]-2,7-diketophosphepin (DTDKP) building block have been studied for the first time. Theoretical calculations predict DTDKP to be a better electron acceptor than the well-known dithienophosphole and the nitrogen analogue, bithiopheneimide. Cyclic voltammetry studies revealed two reduction processes that support their promising electron-acceptor properties, and modification of the P center with O or gold(I) further reduced the LUMO energy to ca. -3.6 eV. Expansion of the DTDKP core with various aromatic moieties has been realized using the Huisgen alkynyl click reaction, resulting in altered optical and electrochemical properties with compounds showing a high-energy absorption band at ca. 270-290 nm and a low-energy band at ca. 390-460 nm. The acceptor character of the DTDKP core was demonstrated by a red shift following the electron-donating strength of the appended aromatic moiety. Intriguing white-light emission from just a single species with the CIE coordinates of (0.33, 0.34) was observed for some of the extended species as the result of an unexpected dual-emission behavior. The high-energy emission in the blue-to-green region and the low-energy emission in the orange-to-red region are attributed to a pi* -> pi transition of the DTDKP core and charge transfer from the triazole moiety to DTDKP, respectively. Apart from tuning of the molecular properties, this novel building block has also been applied in a self-assembled organogel, which exhibited pronounced luminescence. Scanning electron microscopy confirmed that the gel self-assembled by forming a network of entangled ID fibrous structures on the micrometer scale.

  DOI：

  10.1021/ja310680x

文献信息

• Fluoride catalyzed P–aryl-coupling—a mild approach to functionalized arylphosphines
  作者：Andreas Reis、Daniel Dehe、Saeid Farsadpour、Isabel Munstein、Yu Sun、Werner R. Thiel

  DOI：10.1039/c1nj20448c

  日期：——

  Functionalized triaryl- and diarylalkylphosphines are accessible in high yields following a mild fluoride catalyzed phosphorous–carbon coupling protocol starting from fluoroarenes and silylated phosphines. The reaction requires a minimum of solvent and can be applied to the synthesis of several functionalized phosphines on a kilogram scale without problems. In contrast to the phosphine synthesis in a superbasic medium, there is no salt formation during the reaction which simplifies the work-up process.

  经过温和的氟化物催化磷-碳偶联反应，可以从氟代芳烃和硅烷化的膦高效地获得高产率的官能化三芳基膦和二芳基烷基膦。该反应所需的溶剂最少，并且可以在不遇到问题的情况下应用于公斤级规模的多种官能化膦的合成。与在超碱介质中进行的膦合成不同，反应过程中没有盐的形成，从而简化了后续处理流程。
• Cyclic carboxylic monophosphides: a new class of phosphorus heterocycle
  作者：Andrew R. Barron、Stephen W. Hall、Alan H. Cowley

  DOI：10.1039/c39870001753

  日期：——

  Bis(trimethylsilyl)phosphines, RP(SiMe3)2(R = Ph, But), react with di-acid chlorides or the corresponding acid anhydrides to afford cyclic carboxylic monophosphides featuring five-, six- or seven-membered phosphorus-containing rings; the reaction chemistry of the five-membered ring is discussed.

  双（三甲基甲硅烷基）膦，RP（SiMe 3）2（R = Ph，Bu t），与二酰氯或相应的酸酐反应，生成具有五，六或七元含磷特征的环状羧酸单磷化物戒指; 讨论了五元环的反应化学。
• Oligonuclear Tricarbonylchromium- and Tricarbonyltungsten Derivatives of Tris(1-cyclohepta-2,4,6-trienyl)phosphane, P(C₇H₇)₃, and Related Ligands
  作者：Max Herberhold、Kurt Bauer、Wolfgang Milius

  DOI：10.1515/znb-1999-0114

  日期：1999.1.1

  A series of trinuclear carbonylmetal complexes of tri(1-cyclohepta-2,4,6-trienyl)phosphane, P(C7H7)3 (1), has been prepared by the reaction of P(SiMe3)3 with η7-tropylium halfsandwich salts, [(η7-C7H7)M(CO)3]BF4, (M = Cr, Mo, W). While phosphorus remains uncoordinated in the chromium complex P[(η6-C7H7)Cr(CO)3]3 (2a), the molybdenum and tungsten analogues, (M = Mo (2b), W (2c)), contain a coordinated

  通过P(SiMe3)3与η7-tropylium半夹心盐反应制备了一系列三(1-环庚-2,4,6-三烯基)膦的三核羰基金属配合物P(C7H7)3 (1) , [(η7-C7H7)M(CO)3]BF4, (M = Cr, Mo, W)。虽然磷在铬络合物 P[(η6-C7H7)Cr(CO)3]3 (2a) 中保持未配位，但钼和钨类似物（M = Mo (2b), W (2c)）含有配位磷原子与 η4-去甲二烯基取代基一起。2a 与五羰基金属碎片 [M(CO)5] 的反应产生三核产物 - (CO)4][(η-C7H7)M(CO)3]2 (M = Cr (5a), W (5c) ))，其中磷与 η2-环庚三烯基取代基相邻配位。几种含有 [(η6-C7H7)Cr(CO)3] 取代基 (X) 的烷基和芳基膦，例如 Ph2P(X) (6a)、RP(X)2 (R = Me (7a)、CH2Ph (8a)、 Ph
• Thieno[3,4-<i>c</i> ]phosphole-4,6-dione: A Versatile Building Block for Phosphorus-Containing Functional π-Conjugated Systems
  作者：Youhei Takeda、Kota Hatanaka、Takuya Nishida、Satoshi Minakata

  DOI：10.1002/chem.201602392

  日期：2016.7.18

  A versatile phosphorus‐containing π‐conjugated building block, thieno[3,4‐c]phosphole‐4,6‐dione (TPHODO), has been developed. The utility of this simple but hitherto unknown building block has been demonstrated by preparing novel functional organophosphorus compounds and bandgap‐tunable conjugated polymers.

  已经开发了一种通用的含磷π共轭结构单元，thieno [3,4- c ]磷-4,6-二酮（TPHODO）。通过制备新型功能性有机磷化合物和能带隙可调的共轭聚合物，已证明了这种简单但迄今未知的结构单元的实用性。
• Phosphacycloalkyldiones: synthesis and coordinative behaviour of 6- and 7-member cyclic diketophosphanyls
  作者：Kyle G. Pearce、Vladimir Simenok、Ian R. Crossley

  DOI：10.1039/d0dt00864h

  日期：——

  Glutaryl and adipoyl chlorides undergo facile condensation with the bis(silyl)phosphanes RP(SiMe3)2 (R = Me, nBu, tBu, Ph, Mes) to afford exclusively the phosphacycloalkyldiones (CH2)n(C[double bond, length as m-dash]O)2PR (n = 3, 4). Characterised spectroscopically and, for R = Ph, Mes (n = 3) crystallographically, the macrocycles are conformationally fluxional in solution and appreciably moisture

  戊二酰氯和己二酰氯与双（甲硅烷基）膦RP（SiMe3）2（R = Me，nBu，tBu，Ph，Mes）容易缩合，仅得到磷环烷基二酮（CH2）n（C [双键，长度为m -破] O）2 PR（n ＝ 3、4）。在光谱上表征，对于R = Ph，在结晶学上为Mes（n = 3）表征，大环在溶液中呈构象流动，并且对水分敏感。尽管看似对磷的化学氧化具有抗性，但很容易实现配位，如反式-[Pt（PEt3）P（Ph）（CO）2（CH2）3} Cl2]和一系列五羰基钨配合物的分离所示，通过结晶学，红外光谱和NMR光谱对其进行表征。这些数据共同表明，大环是相对弱的σ供体，没有明显的π受体特征。