diethyl 1-hydroxy-1-phenylethylphosphonate | 34881-11-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 1-hydroxy-1-phenylethylphosphonate
• 英文别名: diethyl α-hydroxy-α-methylbenzylphosphonate；diethyl (1-hydroxy-1-phenyl)eth-1-ylphosphonate；diethyl (1-hydroxy-1-phenyl-ethyl)phosphonate；diethyl (1-hydroxy-1-phenyl)ethylphosphonate；diethyl (1-hydroxy-1-phenylethyl)phosphonate；diethyl 1-hydroxy-1-(phenyl)ethylphosphonate；1-Diethoxyphosphoryl-1-phenylethanol
• CAS: 34881-11-3
• 化学式: C₁₂H₁₉O₄P
• 分子量: 258.254
• InChiKey: XAOWLBAJYUPADQ-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  151 °C(Press: 10 Torr)
• 密度：
  1.1224 g/cm3(Temp: 420 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-hydroxy-1-phenylethylphosphonate 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 Methanesulfonic acid 1-(diethoxy-phosphoryl)-1-phenyl-ethyl ester
  参考文献：
  名称：

  Mesylate derivatives of .alpha.-hydroxy phosphonates. Formation of carbocations adjacent to the diethyl phosphonate group

  摘要：

  DOI：

  10.1021/ja00347a054
• 作为产物：
  描述：

  Diethyl-α,α-methyltrimethylsiloxybenzylphosphonat 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 以88%的产率得到diethyl 1-hydroxy-1-phenylethylphosphonate
  参考文献：
  名称：

  Mesylate derivatives of .alpha.-hydroxy phosphonates. Formation of carbocations adjacent to the diethyl phosphonate group

  摘要：

  DOI：

  10.1021/ja00347a054

文献信息

• An efficient method for the phosphonation of C=X compounds
  作者：A. O. Kolodyazhnaya、O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s1070363210040055

  日期：2010.4

  (aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins) in the presence of amines and anilines hydrohalides was studied. We found that pyridine hydrohalides effectively activate the reaction of tralkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated

  在胺和苯胺​​氢卤化物存在下，研究了亚磷酸三烷基酯与C = X亲电试剂（醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化烯烃）的反应。我们发现吡啶氢卤化物有效地激活了亚磷酸三烷基酯与各种C = X亲电试剂的反应：醛，酮，酮膦酸酯，醛亚胺，酮亚胺，异氰酸酯，异硫氰酸酯和活化的烯烃。特别高的活性显示出吡啶氢碘化物。该反应是合成羟基膦酸酯，氨基膦酸酯，氨基甲酰基膦酸酯，氨基甲酰基硫代膦酸酯和亚甲基双膦酸酯的便利方法。
• Reactions of acyl tributylphosphonium chlorides and dialkyl acylphosphonates with Grignard and organolithium reagents
  作者：Hatsuo Maeda、Kenji Takahashi、Hidenobu Ohmori

  DOI：10.1016/s0040-4020(98)00767-4

  日期：1998.10

  Ketones and esters (4) were effectively prepared by reaction of Grignard reagents with acyl tributylphosphonium chlorides (2), diethyl acylphosphonates (5), or diisopropyl acylphosphonate (6) derived from acid chlorides and chloroformates (1). Although by the method with 2, 4 is prepared in one-pot operation from 1 and generally in a higher yield, the method with 5 or 6 proved to compensate for the

  酮和酯（4）进行了有效通过与酰基三丁基氯化物（格氏试剂反应而制备2），二乙基acylphosphonates（5），或二异丙酰基膦酸酯（6从酰氯和氯甲酸酯（派生）1）。虽然通过该方法2，4是在单罐操作制备从1且通常在一个更高的产率，该方法5或6证明，以补偿的合成4用2在某些方面。的反应性2，5，并还通过比较它们的还原电位与酰基氯的还原电位来评估6作为亲电试剂。
• <i>O</i>-Allylated Pudovik and Passerini Adducts as Versatile Scaffolds for Product Diversification
  作者：Mansour Dolé Kerim、Tania Katsina、Martin Cattoen、Nicolas Fincias、Stellios Arseniyadis、Laurent El Kaïm

  DOI：10.1021/acs.joc.0c01721

  日期：2020.10.2

  The palladium-catalyzed O-allylation of α-hydroxyphosphonates and α-hydroxyamides obtained from Pudovik and Passerini multicomponent reactions has allowed interesting and highly straightforward access to a variety of building blocks for product diversification. These post-functionalizations include a selective base- or ruthenium hydride-mediated isomerization/Claisen rearrangement cascade and a ring-closing

  从Pudovik和Passerini多组分反应中获得的钯催化的α-羟基膦酸酯和α-羟基酰胺的O-烯丙基化使人们能够有趣而又直接地获得用于各种产品多样化的结构单元。这些后功能化包括选择性的碱金属或钌氢化物介导的异构化/克莱森重排级联和闭环复分解，该复分解允许进入各种不同功能化的膦酰基-氧杂杂环。
• Palladium-catalysed<i>O</i>-Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles
  作者：Mansour Dolé Kerim、Martin Cattoen、Nicolas Fincias、Aurélie Dos Santos、Stellios Arseniyadis、Laurent El Kaïm

  DOI：10.1002/adsc.201701150

  日期：2018.2.1

  We report here an unprecedented palladium-catalysed O-allylation of α-hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji-Trost type O-allylation/Ring-Closing Metathesis to afford a variety of phosphorylated heterocycles of various sizes ranging from 5 to 16 starting from readily available aldehydes.

  我们在这里报告了史无前例的钯催化α-羟基膦酸酯的O-烯丙基化。该方法最终被包括在顺序的Pudovik / Tsuji-Trost型O-烯丙基化/环封闭复分解中，以提供从易于获得的醛开始的5至16范围大小不等的各种磷酸化杂环。
• Highly Effective Alkaline Earth Catalysts for the Sterically Governed Hydrophosphonylation of Aldehydes and Nonactivated Ketones
  作者：Bo Liu、Jean-François Carpentier、Yann Sarazin

  DOI：10.1002/chem.201201489

  日期：2012.10.15

  Down‐to‐earth catalysis: Heteroleptic and, more interestingly, homoleptic complexes of the large alkaline earth metals (calcium, strontium, and barium) constitute remarkably efficient catalysts for hydrophosphonylation reactions of aldehydes and nonactivated ketones (see scheme). Perfect chemoselectivities and unprecedented turnover frequencies (TOFs) are reported.

  脚踏实地的催化作用：大型碱土金属（钙，锶和钡）的杂合剂，更有趣的是，均合的配合物构成了醛和未活化酮的氢膦酰化反应的高效催化剂（参见方案）。完美的化学选择性和空前的周转频率（TOFs）报道。