isopentyl diphenylphosphinate | 41044-86-4

• 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: isopentyl diphenylphosphinate
• 英文别名: Diphenyl-phosphinic acid 3-methyl-butyl ester；[3-methylbutoxy(phenyl)phosphoryl]benzene
• CAS: 41044-86-4
• 化学式: C₁₇H₂₁O₂P
• 分子量: 288.326
• InChiKey: ZZDRCASVJOWGKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 2-(2-吡啶)-苯并咪唑 、 二苯基硅烷 、 三乙胺 、 magnesium chloride 、 nickel dichloride 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 生成 isopentyl diphenylphosphinate
  参考文献：
  名称：

  锌介导的叔烷基草酸酯的加氢脱氧

  摘要：

  本文中，我们描述了在Ni催化条件下通过Zn /硅烷对易获得的叔烷基草酸酯进行加氢脱氧的一般，温和和可扩展的方法。还原方法适用于衍生自带有不同官能团的叔醇的一系列结构基序，包括在通往雌酮的途中合成关键中间体。

  DOI：

  10.1055/a-1328-0352

文献信息

• A “green” variation of the Hirao reaction: the P–C coupling of diethyl phosphite, alkyl phenyl-<i>H</i>-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)₂ catalyst under microwave and solvent-free conditions
  作者：György Keglevich、Erzsébet Jablonkai、László B. Balázs

  DOI：10.1039/c4ra03292f

  日期：——

  The P–C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc)2 catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free conditions to afford diethyl arylphosphonates, alkyl diphenylphosphinates, aryldiphenylphosphine oxides and

  亚磷酸二乙酯，烷基苯基H-次膦酸酯，二苯基膦氧化物和二烷基膦氧化物与溴芳烃的P–C偶联可在无P配体的Pd（OAc）2催化剂和三乙胺存在下于微波辅助下进行（MW ）和几乎所有情况下的无溶剂条件，分别得到芳基二乙基膦酸酯，烷基二苯基次膦酸酯，芳基二苯基膦氧化物和二烷基苯基膦氧化物。这是众所周知的Hirao反应的“最绿色”完成，现已发现该反应已普遍应用于具有不同反应性的各种> P（O）H物种，以及多种取代的溴苯。烷基苯基-H-phosphinates由苯基的MW-促进烷基化制备ħ在不存在任何溶剂的次膦酸。
• Synthesis and study of the antiinflammatory and analgesic activity of some phosphinic acid esters
  作者：B. K. Beznosko、V. M. Usanova、L. V. Zhuravleva、V. E. Baulin、A. N. Yarkevich、V. Kh. Syundyukova、E. N. Tsvetkov

  DOI：10.1007/bf02464249

  日期：1997.12

  in its activity with acetylsalicylic acid. In contrast to the latter acid, this oxide produces no ulcerogenic effect even at a dose of 1/3 LD50. Therefore, it was of interest to continue the search for new antiinflammatory and analgesic agents in the series of phosphoryl-containing compounds. The purpose of this work was to study the antiinflammatory and analgesic properties and the acute toxicity of

  众所周知，1,1-二甲基-3-氧代丁基膦酸二甲酯（二甲膦）具有抗炎特性，但其作用机制与已知的经典非甾体药物不同 [1]。最近我们已经证明一些烷基二苯基膦氧化物具有抗炎和/或镇痛特性 [2]。这些化合物中活性最强的异戊基二苯基氧化膦具有相当低的毒性，其活性与乙酰水杨酸相当。与后一种酸相比，这种氧化物即使在 1/3 LD50 的剂量下也不产生溃疡作用。因此，继续在含磷酰基化合物系列中寻找新的抗炎和镇痛剂是很有意义的。这项工作的目的是研究二苯基次膦酸 (I XVII) 和二丁基次膦酸 (XVIII) 的一些烷基酯和丙烯酸酯的抗炎和镇痛特性以及急性毒性。大多数二苯基和二丁基次膦酸的酯是在苯介质中，在碱（三乙胺或吡啶）存在下，通过它们的氯酐与相应的醇或酚的相互作用获得的：
• Ti-Catalyzed Dehydroxylation of Tertiary Alcohols
  作者：Quan Lin、Weiqi Tong、Xing-Zhong Shu、Yunrong Chen

  DOI：10.1021/acs.orglett.2c03119

  日期：2022.11.25

  Herein we report a Ti-catalyzed direct dehydroxylation of tertiary aliphatic alcohols under mild reaction conditions, forging Barton-type deoxygenation products. This protocol tolerates a wide range of functional groups, including primary alkyl chloride and carbonyl groups. It allows for selective dehydroxylation of tertiary alcohols in diols and the formation of deuterated products with moderate deuterium

  在此，我们报告了在温和反应条件下钛催化的脂肪族叔醇直接脱羟基反应，形成了 Barton 型脱氧产物。该协议容忍范围广泛的功能组，包括初级烷基氯和羰基。它允许二醇中的叔醇选择性脱羟基，并形成具有适度氘掺入的氘化产物。几种药物和天然产物（或其衍生物）的有效修饰突出了该方法的合成效用。
• Direct Aerobic Oxidative Esterification and Arylation of P(O)–OH Compounds with Alcohols and Diaryliodonium Triflates
  作者：Biquan Xiong、Xiaofeng Feng、Longzhi Zhu、Tieqiao Chen、Yongbo Zhou、Chak-Tong Au、Shuang-Feng Yin

  DOI：10.1021/cs501523g

  日期：2015.2.6

  Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.
• Synthesis and characterisation of severely hindered P-OR compounds
  作者：D. Bradley G. Williams、Takelani E. Netshiozwi

  DOI：10.1016/j.tet.2009.10.008

  日期：2009.11

  P-Cl substrates were converted into their P-OR analogues from hindered alcohols using an amine base. Where the system was severely hindered, more forcing conditions were required that necessitated the presence of a metal alkoxide nucleophile before successful reactions were observed. In some instances, the products were thermally unstable and reverted to alkenes by elimination reactions, while others were sensitive to moisture. Here, hydrolysis products prevailed if moisture was not rigorously excluded. Details are presented to obtain the P(III) and P(V) esters, diesters and half esters. (C) 2009 Elsevier Ltd. All rights reserved.