P-[(4-溴苯基)甲基]-膦酸二甲酯 | 17211-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: P-[(4-溴苯基)甲基]-膦酸二甲酯
• 英文名称: dimethyl 4-bromobenzylphosphonate
• 英文别名: 1-Bromo-4-(dimethoxyphosphorylmethyl)benzene
• CAS: 17211-08-4
• 化学式: C₉H₁₂BrO₃P
• 分子量: 279.07
• InChiKey: UGQVUWCKOLSYSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  349.3±25.0 °C(Predicted)
• 密度：
  1.454±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别码：
  R36/37/38,R
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  P-[(4-溴苯基)甲基]-膦酸二甲酯 在 四(三苯基膦)钯 、 正丁基锂 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-[4-(2,2-diphenylvinyl)phenyl]pyrene
  参考文献：
  名称：

  Suppression of aggregation-induced fluorescence quenching in pyrene derivatives: photophysical properties and crystal structures

  摘要：

  Two new pyrene-based fluorophores, namely 1-[4-(2,2-diphenylvinyl)phenyl]pyrene (PVPP) and 1,3,6, 8-tetrakis[4-(2,2-diphenylvinyl)phenyl]pyrene (TPVPP), were synthesized through Suzuki coupling reaction and well characterized. PVPP successfully suppresses the fluorescence quenching of pyrene units in the solid state, displaying aggregation-induced enhanced emission. Despite the same substituent, TPVPP shows a different fluorescent behavior. On the basis of the crystal structures, the distinct optical behavior is discussed and clarified. The intermolecular C-H center dot center dot center dot pi interaction has a dramatic effect on their photophysical properties in the solid state. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.060
• 作为产物：
  描述：

  对溴溴苄 、 三甲氧基磷 以98%的产率得到P-[(4-溴苯基)甲基]-膦酸二甲酯
  参考文献：
  名称：

  用N-氟苯磺酰亚胺通过苄基膦酸酯的α-碳负离子的亲电氟化反应合成芳基（二氟亚甲基膦酸酯）

  摘要：

  已经研究了多种苄基膦酸酯与N-氟苯磺酰亚胺的亲电子氟化。在一系列官能团如硝基，溴，酮，酯，苯基和醚基的存在下，氟化反应进行得很好。也可以制备含有两个α，α-二氟亚甲基膦酸酯基的苯基和联苯衍生物。该方法与甲基或乙基膦酸酯相容，但是与叔丁基酯或在对位处含有另外的苄基部分的苄基膦酸酯不相容。

  DOI：

  10.1016/s0040-4020(97)10395-7

文献信息

• A convergent synthesis of (diphenylvinyl)benzene (DPVB) star-shaped compounds with tunable redox, photo- and electroluminescent properties
  作者：Rafael Gómez、Dirk Veldman、Bea M. W. Langeveld、José L. Segura、René A. J. Janssen

  DOI：10.1039/b707496d

  日期：——

  In this paper we describe a convenient and convergent approach to the synthesis of novel and highly luminescent (diphenylvinyl)benzene (DPVB)-based conjugated star-shaped molecules, which can be used as emitting dyes in doped OLEDs. The versatility of this synthetic route allows tuning of the HOMO–LUMO energy levels of the materials by means of the introduction of different electroactive peripheral groups. Two related star-shaped dyes have been prepared, one with amine and one with alkoxy end groups, and have been characterized using optical spectroscopy and cyclic voltammetry. The energy levels of the dyes are found to lie within the band gap of a polyfluorene (PF) derivative such that energy transfer from the photoexcited PF to the dyes takes place. In OLEDs that contain 1 wt% of dye in PF, the emission is predominantly from the dye. Although the EL spectra are similar for the two dyes, other device characteristics differ greatly. OLEDs using the amine-terminated dye have a luminance that is a few orders of magnitude lower than that based on the alkoxy-terminated dye. The differences are explained by the positioning of the HOMO and LUMO levels of the two dyes compared to those of PF. The dye with the amine end group can act as a deep trap for holes, reducing charge transport in the film.

  本文描述了一种方便且收敛的方法来合成新型且高发光的（二苯乙烯基）苯（DPVB）基共轭星形分子，这些分子可作为掺杂OLED中的发光染料。该合成路线的多功能性允许通过引入不同的电活性周边基团来调节材料的HOMO-LUMO能级。制备了两种相关的星形染料，一种带有胺端基，另一种带有烷氧基端基，并利用光谱学和循环伏安法进行了表征。发现这些染料的能级位于聚芴（PF）衍生物的带隙内，使得从光激发的PF到染料的能量转移得以进行。在含有1 wt%染料的PF的OLED中，发射主要来自染料。尽管两种染料的EL光谱相似，但其他器件特性差异很大。使用胺端基染料的OLED的亮度比基于烷氧基端基染料的OLED低几个数量级。这些差异可以通过两种染料的HOMO和LUMO能级相对于PF的能级位置来解释。带有胺端基的染料可以作为深阱捕获空穴，减少了薄膜中的电荷传输。
• Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes
  作者：Quentin Lefebvre、Marc Jentsch、Magnus Rueping

  DOI：10.3762/bjoc.9.221

  日期：——

  A continuous flow oxidative photocyclization of stilbene derivatives has been developed which allows the scalable synthesis of backbone functionalized phenanthrenes and helicenes of various sizes in good yields.

  已经开发了二苯乙烯衍生物的连续流动氧化光环化，它允许以良好的产率大规模合成各种尺寸的骨架官能化菲和螺旋。
• REACTIVITY OF THE ACIDS OF TRIVALENT PHOSPHORUS AND THEIR DERIVATIVES. PART VI. THE REACTION OF THE &gt;P—O⁻ ANIONS WITH BENZYL BROMIDES <i>para</i>-SUBSTITUTED IN THE PHENYL RING
  作者：Dariusz Witt、Janusz Rachon

  DOI：10.1080/10426509608029649

  日期：1996.1.1

  Abstract The reaction of p-substituted benzyl bromides with the >P—O− ions in THF, alcohols and toluene as the solvents is described. According to the reduction potential of the p-substituted benzyl bromides and the solvent used the formation of the P—C bond, debromination and/or dimerization occur. The principal process is believed to be X-philic substitution, the dimers are formed through a secondary

  摘要 描述了对取代苄基溴与 >PO- 离子在四氢呋喃、醇和甲苯作为溶剂中的反应。根据对位取代苄基溴化物的还原电位和所用溶剂形成PC键，发生脱溴和/或二聚反应。主要过程被认为是亲 X 取代，二聚体通过二次过程通过 SET 从对位取代的苄基阴离子形成对位取代的苄基溴。
• Synthesis of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) via electrophilic fluorination
  作者：Scott D. Taylor、A.Nicole Dinaut、Avinash N. Thadani、Zheng Huang

  DOI：10.1016/0040-4039(96)01847-3

  日期：1996.11

  A series of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) have been prepared via electrophilic fluorination of the corresponding benzylic phosphonates.

  通过相应的苄基膦酸酯的亲电氟化，制备了一系列苄基单（α，α-二氟甲基膦酸酯）和苄基双（α，α-二氟甲基膦酸酯）。
• One-Pot Synthesis of 1,4-Diarylnaphthalenes via a Wittig-Horner Reaction/[4+2] Cycloaddition/Dehydrogenation Sequence
  作者：Yanguang Wang、Zhengbo Chen、Wangge Shou

  DOI：10.1055/s-0028-1083356

  日期：2009.4

  A one-pot synthesis of 1,4-diarylnaphthalenes from cinnamaldehydes, dimethyl benzylphosphonates, and benzenediazonium-2-carboxylate is described. The tandem process involves the Wittig-Horner reaction of the cinnamaldehyde with the benzylphosphonate, [4+2] cycloaddition of the thus-formed diene with benzyne, and subsequent dehydrogenation. The procedure is general and efficient and the substrates are

  描述了由肉桂醛，二甲基苄基膦酸酯和苯重氮-2-羧酸酯一锅法合成1,4-二芳基萘。串联过程涉及肉桂醛与苄基膦酸酯的Wittig-Horner反应，由此形成的二烯与苯炔的[4 + 2]环加成以及随后的脱氢。该过程是通用且有效的，并且衬底容易获得。 二苯基萘-串联反应-Wittig-Horner反应-环加成反应-苯并