dimethyl 1-hydroxy-1-(4-trifluoromethylphenyl)methylphosphonate | 1333211-11-2

• 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: dimethyl 1-hydroxy-1-(4-trifluoromethylphenyl)methylphosphonate
• 英文别名: dimethyl α-hydroxy-4-trifluoromethylbenzylphosphonate；[Dimethoxy(oxido)phosphaniumyl]-[4-(trifluoromethyl)phenyl]methanol；[dimethoxy(oxido)phosphaniumyl]-[4-(trifluoromethyl)phenyl]methanol
• CAS: 1333211-11-2
• 化学式: C₁₀H₁₂F₃O₄P
• 分子量: 284.172
• InChiKey: SEJZICYGSOTNOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 1-hydroxy-1-(4-trifluoromethylphenyl)methylphosphonate 在 盐酸 、 水 作用下， 生成 1-(4-trifluoromethylphenyl)-1-hydroxymethylphosphonic acid
  参考文献：
  名称：

  次膦酸盐和膦酸盐的水解和醇解

  摘要：

  摘要 次膦酸和膦酸有用的中间体和生物活性化合物可以分别由它们的酯制备：次膦酸盐和膦酸盐，通过酸催化水解在常规加热或MW照射下进行。烷基次膦酸盐的酯交换反应仅在合适的离子液体作为催化剂存在的情况下进行。在苯基膦酸盐的情况下，取决于离子液体的性质，酯的形成伴随着 C-O 键的裂变。

  DOI：

  10.1080/10426507.2021.1991345
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 二甲基三甲硅基膦酸酯 在 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.5h， 以81%的产率得到dimethyl 1-hydroxy-1-(4-trifluoromethylphenyl)methylphosphonate
  参考文献：
  名称：

  N-杂环碳催化醛的氢膦酰化

  摘要：

  已开发出N-杂环卡宾催化的亚甲基三甲基甲硅烷基亚磷酸酯与醛的Pudovik型反应，以构建碳-磷键，从而以中等至优异的产率提供α-羟基膦酸酯。 N-杂环卡宾-Pudovik型反应-α-羟基膦酸酯-醛-CP键

  DOI：

  10.1055/s-0030-1260045

文献信息

• Ultrasound assisted green synthesis of α-hydroxyphosphonates under solvent-free conditions
  作者：Abdeslem Bouzina、Nour-eddine Aouf、Malika Berredjem

  DOI：10.1007/s11164-015-2420-8

  日期：2016.6

  Abstract A simple, efficient and environmentally benign method for the synthesis of α-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is effectively accomplished under ultrasound irradiation and solvent-free and catalyst-free conditions. This rapid method produces α-hydroxyphosphonates in high yields and short reaction times. Graphical Abstract

  摘要 通过醛或酮与亚磷酸三烷基酯的反应合成α-羟基膦酸酯的简单，有效，环境友好的方法在超声辐射，无溶剂和无催化剂的条件下有效地实现。这种快速的方法可以高产率和短反应时间生产α-羟基膦酸酯。 图形概要
• Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
  作者：Nikoletta Harsági、Zita Rádai、Áron Szigetvári、János Kóti、György Keglevich

  DOI：10.3390/molecules25173793

  日期：——

  acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The

  监测 α-羟基苄基膦酸酯和一些相关衍生物的两步酸性水解，以确定动力学并绘制不同取代的膦酸酯在水解中的反应性。吸电子取代基增加了速率，而放电子取代基减慢了反应速度。两个水解步骤都以伪一级速率常数为特征。发现第二个 POC 键的裂变是决定速率的步骤。
• Synthesis and insecticidal activities of <i>O,O</i>-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1<i>H</i>-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
  作者：Wei Wang、Lie-Ping Wang、Bin-Ke Ning、Ming-Zhen Mao、Chao Xue、Hai-Yang Wang

  DOI：10.1080/10426507.2016.1206103

  日期：2016.10.2

  A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1-14 were designed and synthesized. The structures of all the title compounds were confirmed by H-1-NMR, C-13-NMR, P-31-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20-80% larvicidal activity against Mythimna separata at 1000mg/L.[GRAPHICS].
• <i>N</i>-Heterocyclic Carbenes Catalyzed Phospho-Aldol Reaction of Aldehydes
  作者：Lin He、Zhihua Cai、Xiaowei Ma、Guangfen Du

  DOI：10.1002/cjoc.201300615

  日期：2013.12

  AbstractAn efficient phospho‐aldol reaction of aldehydes catalyzed by N‐heterocyclic carbenes (NHCs) has been developed. With 10 mol% stable NHC 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene, various aldehydes reacted with dialkylphosphites smoothly to provide α‐hydroxy phosphonates in 59% –99% yield. In this process, NHC was assumed to function as a carbon‐centered br?nsted base.
• N-Heterocyclic Carbene Catalyzed Hydrophosphonylation of Aldehydes
  作者：Lin He、Zhi-Hua Cai、Guang-Fen Du、Cheng-Zhi Gu、Bin Dai

  DOI：10.1055/s-0030-1260045

  日期：2011.7

  N-Heterocyclic carbene catalyzed Pudovik-type reaction of dimethyl trimethylsilyl phosphite and aldehydes for the construction of carbon-phosphorus bonds have been developed, providing α-hydroxyphosphonates in moderate to excellent yield. N-heterocyclic carbene - Pudovik-type reaction - α-hydroxyphosphonates - aldehydes - C-P bond

  已开发出N-杂环卡宾催化的亚甲基三甲基甲硅烷基亚磷酸酯与醛的Pudovik型反应，以构建碳-磷键，从而以中等至优异的产率提供α-羟基膦酸酯。 N-杂环卡宾-Pudovik型反应-α-羟基膦酸酯-醛-CP键