methyl 3-(diethoxyphosphinyl)-propanoate | 1112-94-3

• 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: methyl 3-(diethoxyphosphinyl)-propanoate
• 英文别名: Methyl 3-(diethoxyphosphoryl)propionate；methyl 3-(diethoxyphosphoryl)propanoate；3-diethoxyphosphoryl-propionic acid methyl ester；3-Diaethoxyphosphoryl-propionsaeure-methylester；3-(diethoxyphosphinyl)-propanoic acid, methyl ester；3--propionsaeure-methylester；methyl 3-diethoxyphosphorylpropanoate
• CAS: 1112-94-3
• 化学式: C₈H₁₇O₅P
• mdl: MFCD00137949
• 分子量: 224.194
• InChiKey: TXMSAFGVEZUMPX-UHFFFAOYSA-N

物化性质

• 沸点：
  103.0-103.2 °C(Press: 0.4 Torr)
• 密度：
  1.1181 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(diethoxyphosphinyl)-propanoate 在 三甲基溴硅烷 作用下， 生成 (3-甲氧基-3-氧代丙基)膦酸
  参考文献：
  名称：

  New inhibitors of rabbit muscle triose-phosphate isomerase

  摘要：

  We describe the synthesis and evaluation of three new competitive inhibitors of triose-phosphate isomerase. One of them (phosphoglycoloamidoxime: K-i = 4.5 mu M) is among the best reversible inhibitors so far reported for this enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.061
• 作为产物：
  描述：

  diethyl 3-methoxy-3-(trimethylsiloxy)-2-propenephosphonate 在 水 作用下， 以 乙醚 为溶剂， 反应 0.08h， 生成 methyl 3-(diethoxyphosphinyl)-propanoate
  参考文献：
  名称：

  Preparation of (Dialkoxyphosphinyl)-methyl-Substituted Ketene Alkyl Trimethylsilyl Acetal Derivatives

  摘要：

  DOI：

  10.1055/s-1982-29854

文献信息

• A green procedure for the regio- and chemoselective hydrophosphonylation of unsaturated systems using CaO under solventless conditions
  作者：Elisa Martínez-Castro、Óscar López、Inés Maya、José G. Fernández-Bolaños、Marino Petrini

  DOI：10.1039/c0gc00026d

  日期：——

  Diethyl phosphite and diphenylphosphine add to a series of unsaturated derivatives using environmentally-friendly calcium oxide as a basic promoter under solventless conditions at room temperature. The corresponding adducts are obtained in a totally regioselective fashion, via a 1,4-addition on α,β-unsaturated esters and sulfone, and a 1,2-addition on cyclic and acyclic α,β-unsaturated aldehydes and

  亚磷酸二乙酯 和 二苯膦 使用环保添加到一系列不饱和衍生物中 氧化钙在室温下于无溶剂条件下作为碱性促进剂。相应的加合物在一个完全区域选择性的方式获得，通过一1,4-加成 α，β-不饱和酯和 砜和 1,2-加成 环和无环α，β-不饱和醛和酮的合成
• Activation anionique du phosphite de diethyle par le fluorure de potassium depose sur alumine, synthese de phosphonates fonctionalises
  作者：Didier Villemin、Rassem Racha

  DOI：10.1016/s0040-4039(00)84375-0

  日期：1986.1

  Dry reactions of diethylphosphite on KF-Al2O3 with different. electrophiles conduct to the synthesis of functionalized phosphonates.

  亚磷酸二乙酯在KF-Al 2 O 3上的干反应有不同。亲电试剂可进行功能化膦酸酯的合成。
• Comparison of catalytic activity of hexamethyltriamino- and tri-n-butylphosphines in the Pudovik reaction
  作者：Alexey V. Salin、Anton V. Il’in

  DOI：10.1080/10426507.2018.1542403

  日期：2019.5.27

  in the P(O)–H bond addition to electron-deficient alkenes was studied. Depending on the nature of the alkene, hexamethyltriaminophosphine produces better or lower yields of the reaction products compared to tri-n-butylphosphine. Graphical Abstract

  摘要 研究了六甲基三氨基膦对缺电子烯烃的 P(O)-H 键加成的催化活性。取决于烯烃的性质，与三正丁基膦相比，六甲基三氨基膦产生更好或更低的反应产物产率。图形概要
• PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes
  作者：Giacomo Strappaveccia、Luca Bianchi、Simone Ziarelli、Stefano Santoro、Daniela Lanari、Ferdinando Pizzo、Luigi Vaccaro

  DOI：10.1039/c6ob00242k

  日期：——

  PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78–85%) in all cases

  PS-BEMP用作非均相催化剂，用于将磷亲核体的磷-迈克尔加成到各种电子贫乏的烯烃中。加成反应通常在无溶剂条件下用等摩尔量的试剂进行。事实证明，该方案对于添加芳族，非芳族和环状酮非常有效，在所有情况下均具有良好的收率（78-85％）。该方案还扩展到了α，β-不饱和酯和腈，并获得了良好的结果。这表明PS-BEMP是将磷-迈克尔加成至电子贫乏烯烃的良好催化剂。
• Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient Olefins
  作者：Yuriy Slutskyy、Larry E. Overman

  DOI：10.1021/acs.orglett.6b00895

  日期：2016.6.3

  a 1,4-dicarbonyl structural motif by a conjugate addition of the methoxycarbonyl radical to reactive Michael acceptors. The regioselectivity of the addition of this alkoxyacyl radical species to electron-deficient olefins is heavily influenced by the electronic nature of the acceptor, behavior similar to that exhibited by nucleophilic alkyl radicals.

  N-邻苯二甲酰亚胺基草酸甲酯的可见光光氧化还原催化断裂，可通过将甲氧羰基自由基共轭加成至反应性迈克尔受体上来直接构建1,4-二羰基结构基序。这种烷氧基酰基基团向缺电子烯烃中加成的区域选择性在很大程度上受受体电子性质的影响，这种行为类似于亲核烷基自由基所表现出的行为。

表征谱图