benzyl dibutyl phosphate | 28519-15-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: benzyl dibutyl phosphate
• 英文别名: benzyl di-n-butyl phosphate
• CAS: 28519-15-5
• 化学式: C₁₅H₂₅O₄P
• 分子量: 300.335
• InChiKey: CYWAMKAHXBXNOW-UHFFFAOYSA-N

物化性质

• 沸点：
  380.3±21.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(苄基磺酰基)-4-硝基苯 在 辛酸铑 、 2,6-二叔丁基-4-甲基吡啶三氟甲磺酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 benzyl dibutyl phosphate
  参考文献：
  名称：

  区分用于烷基化和芳基化反应的锍叶立德的非叶立基碳硫键断裂

  摘要：

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。

  DOI：

  10.1016/j.cclet.2021.06.069

文献信息

• Cetyltrimethyl ammonium bromide catalysed oxidative cross dehydrogenative coupling of benzylic C(sp³)–H bonds in methylarenes with P(O)–OH compounds
  作者：Hang Li、Jian Lei、Yongping Liu、Yi Chen、Chak-Tong Au、Shuang-Feng Yin

  DOI：10.1039/c8ob02772b

  日期：——

  An efficient metal-free method for the synthesis of organophosphorus compounds via oxidative cross dehydrogenative coupling of benzylic C(sp3)–H bonds in methylarenes with P(O)–OH compounds catalysed by cetyltrimethyl ammonium bromide (CTAB) is reported. Various methylarenes and P(O)–OH compounds are tolerated in the reaction with moderate to good yields. Compared to previous studies, the present study

  有机磷化合物的合成的高效无金属方法通过苄型C（SP的氧化交脱氢偶联3报道）-H债券methylarenes用P（O）-OH的化合物通过十六烷基三甲基溴化铵（CTAB）催化。反应中可耐受各种甲基芳烃和P（O）-OH化合物，产率中等至良好。与以前的研究相比，本研究扩展了底物的范围，并采用了铵盐催化剂（CTAB）和氧化剂（DTBP）的新反应体系。控制和机械实验的结果通常与提出的总体途径一致。该方法可避免使用有毒的P卤素试剂和P（O）-H化合物来合成有机磷化合物。
• Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates
  作者：Muskaan Mahandru‐Gill、Aleema Iqbal、Margarita Damai、Francesco Spiedo、Edward K. Kasonde、Daniel Sykes、Kevin G. Devine、Bhaven Patel

  DOI：10.1002/ejoc.202201101

  日期：2022.11.18

  rearrangement from α-hydroxyphosphonates has been optimized producing a range of benzyl phosphate esters in excellent yields by using 1,5-diazabicyclo(4.3.0)non-5-ene at room temperature. Mechanistic studies, using low temperature 31P-NMR, evidence possible formation of an oxaphosphirane intermediate, supporting previous chemical calculations reported.

  有机磷酸盐在生理过程中非常重要。通过在室温下使用 1,5-二氮杂双环 (4.3.0)non-5-ene，对 α-羟基膦酸盐的 phospha-Brook 重排进行了优化，以优异的产率生产了一系列磷酸苄酯。使用低温31 P-NMR 的机理研究表明，可能形成了一种氧杂磷烷中间体，这支持了之前报道的化学计算。
• Phosphate additives for non-aqueous electrolyte in alkali metal electrochemical cells
  申请人：WILSON GREATBATCH LTD.

  公开号：EP0918364A1

  公开（公告）日：1999-05-26

  An alkali metal, solid cathode, nonaqueous electrochemical cell capable of delivering high current pulses, rapidly recovering its open circuit voltage and having high current capacity, is described. The stated benefits are realized by the addition of at least one phosphate additive to an electrolyte comprising an alkali metal salt dissolved in a mixture of a low viscosity solvent and a high permittivity solvent. A preferred solvent mixture includes propylene carbonate, dimethoxyethane and an alkyl phosphate additive.

  本文介绍了一种碱金属固态阴极非水性电化学电池，它能提供大电流脉冲，迅速恢复开路电压，并具有大电流容量。上述优点是通过在电解液中添加至少一种磷酸盐添加剂实现的，电解液包括溶解在低粘度溶剂和高介电常数溶剂混合物中的碱金属盐。一种优选的混合溶剂包括碳酸丙烯酯、二甲氧基乙烷和一种烷基磷酸盐添加剂。
• Tetrabutylammonium Iodide-Catalyzed Phosphorylation of Benzyl CH Bonds<i>via</i>a Cross-Dehydrogenative Coupling (CDC) Reaction
  作者：Jian Xu、Pengbo Zhang、Xueqin Li、Yuzhen Gao、Ju Wu、Guo Tang、Yufen Zhao

  DOI：10.1002/adsc.201400436

  日期：2014.11.3

  AbstractPhosphate esters play important roles as biological active principles and synthons in chemistry. An efficient metal‐free approach for the synthesis of phosphate esters through sp3 CH activation is described. By using tetrabutylammonium iodide (Bu4NI) as a catalyst and tert‐butyl hydroperoxide (TBHP) as an oxidant, various toluene derivatives and phosphorus nucleophiles are tolerated in this transformation, affording the corresponding products in moderate to good yields.magnified image
• Base-promoted O-deprotonation/alkylation reaction of P(O)–OH compounds with alkyl halides
  作者：Biquan Xiong、Qianqian Ye、Xiaofeng Feng、Longzhi Zhu、Tieqiao Chen、Yongbo Zhou、Chak-Tong Au、Shuang-Feng Yin

  DOI：10.1016/j.tet.2014.10.013

  日期：2014.11

  A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction. (C) 2014 Elsevier Ltd. All rights reserved.