diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate | 1019779-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate
• 英文别名: diethyl (1,3-benzodioxol-5-yl)-hydroxymethylphosphonate；1,3-benzodioxol-5-yl(diethoxyphosphoryl)methanol
• CAS: 1019779-87-3
• 化学式: C₁₂H₁₇O₆P
• 分子量: 288.237
• InChiKey: CIBUVUDTKKQPID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate 在 一水合肼 作用下， 生成 (benzo[1,3]dioxol-5-yl-hydrazino-methyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of 2-Phosphono Alkyl 1,2-Benzisoselenazol-3(2H)-ones

  摘要：

  A series of 2-phosphonoalkyl 1,2-benzisoselenazol-3(2H)-ones were designed and synthesized via reaction 2-chloroselenobenzoyl chloride with 1-hydrazinobenzyl phosphonate. The structures of all new compounds were confirmed by spectroscopic methods and microanalyses.

  DOI：

  10.1080/10426500214892
• 作为产物：
  描述：

  胡椒醛 、 亚磷酸三乙酯 在 D(+)-10-樟脑磺酸 、 水 作用下， 反应 0.2h， 以91%的产率得到diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate
  参考文献：
  名称：

  在常规/超声技术下，有机催化容易且快速获得α-羟基和α-氨基膦酸酯

  摘要：

  在本工作中，证明了在无溶剂条件下成功实施超声辐射以快速合成α-羟基和α-氨基膦酸酯的方法。首次报道了将新型催化剂（樟脑磺酸）与超声技术结合使用。讨论了使用常规方法和超声方法合成α-羟基和α-氨基膦酸酯的比较研究。

  DOI：

  10.1016/j.tetlet.2011.03.138

文献信息

• Asymmetric hydrophosphonylation of aldehydes catalyzed by bifunctional chiral Al(III) complexes
  作者：Shaohua Gou、Xin Zhou、Jun Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2008.01.022

  日期：2008.3

  effective enantioselective hydrophosphonylation of aldehydes. A variety of aromatic, heteroaromatic, condensed-ring, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates for the reaction, and the desired α-hydroxy phosphonate were obtained in good to excellent yields (up to 99%) with moderate to good enantioselectivities (up to 87% ee) under mild conditions (at 0 °C). A possible

  一种新的手性双官能的Al（Ⅲ）配合物的BINOL衍生物，其中载有叔在BINOL的3,3'-位置-胺，已发展为醛的对映选择性有效hydrophosphonylation。发现各种芳族，杂芳族，稠环，α，β-不饱和和脂族醛是反应的合适底物，并且以良好或优异的收率（高达99％）获得了所需的α-羟基膦酸酯。在温和条件下（0°C）具有中等至良好的对映选择性（高达87％ee）。根据实验结果提出了可能的催化循环。
• A Simple Heterogeneous Catalyst for Phosphite Addition on Carbonyl Groups
  作者：Veronica Santacroce、Emanuele Paris、Daniele Cauzzi、Raimondo Maggi、Giovanni Maestri

  DOI：10.1002/ejoc.201501434

  日期：2016.1

  easily recoverable heterogeneous catalyst could efficiently trigger C–P bond formation by selective addition of phosphites to the carbonyl group of aldehydes and ketones. The reactions afford the desired products in good to excellent yields and do not require the presence of a solvent. Furthermore, nearly stoichiometric amounts of reagents could be used as the hydrotalcite catalyst does not cause the

  一种廉价且易于回收的多相催化剂可以通过选择性地将亚磷酸酯加成到醛和酮的羰基上来有效地触发 C-P 键的形成。该反应以良好至极好的收率提供所需产物并且不需要溶剂的存在。此外，可以使用接近化学计量量的试剂，因为即使使用脂肪醛，水滑石催化剂也不会引起羰基衍生物的缩合。
• An Efficient Synthesis of α‐(2,4‐Dichloro‐phenoxyacetoxy)aryl Methyl Phosphonate Monosodium Salts
  作者：Tao Wang、Hong Wu He

  DOI：10.1081/scc-120030691

  日期：2004.12.31

  Abstract A series of α‐(2,4‐dichlorophenoxyacetoxy)aryl methyl phosphonate monosodium salts 6 were synthesized by the reaction of the intermediate 5 with sodium iodide under moderate condition. This method was applied to the synthesis of novel phosphonate derivatives containing sensitive groups such as carboxylic ester to acid, base, or water.

  摘要 通过中间体5与碘化钠在温和条件下反应合成了一系列α-(2,4-二氯苯氧基乙酰氧基)芳基甲基膦酸单钠盐6。该方法用于合成含有敏感基团的新型膦酸酯衍生物，例如对酸、碱或水的羧酸酯。
• A Convenient and Efficient Synthesis of Novel Cyclic Phospholipid Analogues Containing Thio(Seleno) Phosphate-Phosphonate Linkages
  作者：Jia Zhou、Ru-Yu Chen

  DOI：10.1080/00397919808004834

  日期：1998.7

  Abstract Some novel cyclic phospholipid analogues containing the thio(seleno) phosphate-phosphonate linkages have been synthesized in good yields by a convenient one-pot procedure utilizing tris(diethylamino)phosphine activated by iodine as the phosphorylating and ring-closing reagent.

  摘要 使用碘活化的三（二乙氨基）膦作为磷酸化和闭环试剂，通过方便的一锅法合成了一些含有硫代（硒）磷酸酯-膦酸酯键的新型环状磷脂类似物。
• Pyridinium perchlorate: A new catalyst for the reaction of trialkyl phosphites with the C=X electrophiles
  作者：O. O. Kolodyazhnaya、O. I. Kolodyazhnyi

  DOI：10.1134/s107036321102006x

  日期：2011.2

  Pyridinium perchlorate is an effective catalyst for the reaction of trialkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, and activated alkenes. The reaction leads to the formation of alpha-substituted phosphonates in a high yield. Advantages of the new catalyst are its high activity, availability, high product yields, and mild reaction conditions.