1-(diethoxyphosphoryl)vinyl 4-methylbenzenesulfonate | 1309980-37-7

• 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: 1-(diethoxyphosphoryl)vinyl 4-methylbenzenesulfonate
• 英文别名: Diethyl 1-[(4-methylbenzenesulfonyl)oxy]ethene-1-phosphonate；1-diethoxyphosphorylethenyl 4-methylbenzenesulfonate
• CAS: 1309980-37-7
• 化学式: C₁₃H₁₉O₆PS
• 分子量: 334.33
• InChiKey: JJBOQKAABXGCBE-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(diethoxyphosphoryl)vinyl 4-methylbenzenesulfonate 在 palladium 10% on activated carbon 、 甲酸铵 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 diethyl 1-(4-methoxyphenyl)ethylphosphonate
  参考文献：
  名称：

  Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki–Miyaura Cross-Coupling Reactions

  摘要：

  It has been demonstrated for the first time that alpha-phosphonovinyl tosylates could efficiently couple with a range of arylboronic acids to access alpha-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields (60-99%) under mild reaction conditions.

  DOI：

  10.1021/ol503518h
• 作为产物：
  描述：

  对甲苯磺酰氯 、 乙酰亚磷酸二乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以87%的产率得到1-(diethoxyphosphoryl)vinyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  α-膦酰基乙烯基芳基磺酸盐：通过钯催化的铃木反应合成α-取代的乙烯基膦酸盐的有吸引力的伙伴

  摘要：

  通过铃木反应合成α-取代的乙烯基膦酸酯的新的，有吸引力的偶联伙伴已被开发出来。发达的以O为中心的亲电试剂与各种有机硼试剂偶合，以中等至极好的收率得到α-取代的乙烯基膦酸酯。该协议具有广泛的基板范围，温和的条件和高效率。

  DOI：

  10.1002/ejoc.201600056

文献信息

• Negishi反应合成α-烷基乙烯膦酸酯的方法
  申请人：浙江医药高等专科学校

  公开号：CN107827925B

  公开（公告）日：2019-10-18

  本发明公开了一种Negishi反应合成α‑烷基乙烯膦酸酯的方法，具体步骤如下：1）往反应管中加入锌粉；在氮气的保护下，加入碘和无水N,N‑二甲基乙酰胺、1‑溴烷烃，制备烷基锌试剂澄清液；2）往反应器中加入α‑膦酸酯乙烯磺酸酯，醋酸钯，2‑双环己基膦‑2',6'‑二甲氧基联苯；加入无水N,N‑二甲基乙酰胺；室温搅拌下滴加烷基锌试剂澄清液；反应结束后，萃取、干燥；柱层析分离，蒸馏得到α‑烷基乙烯膦酸酯，本发明具有底物普适性广、官能团兼容性好、反应条件温和、反应效率高的优点。
• Synthesis of 5-Phosphonoisoxazol­ine<i>N</i>-Oxides by Selective<i>O</i>-Alkylation of Nitronate Anions
  作者：Vincent Perez、Nicolas Rabasso、Antoine Fadel

  DOI：10.1002/ejoc.201501243

  日期：2016.1

  5-phosphonoisoxazoline N-oxides were prepared in good to excellent yields by selective O-alkylation of nitronate anions with (α-tosyloxyvinyl)phosphonates. A comprehensive study was undertaken to limit the competitive formation of the (β-nitrocyclopropyl)phosphonate resulting from C-alkylation of the ambident nitronate anions. The 5-phosphonoisoxazoline N-oxides thus formed were reduced to the corresponding 5-phosphonoisoxazolines

  通过选择性 O-烷基化硝基阴离子与 (α-甲苯磺酰氧基乙烯基) 膦酸盐，制备了一系列 5-膦酰基异恶唑啉 N-氧化物，收率良好至极好。进行了一项全面的研究以限制由双亲硝基阴离子的 C-烷基化产生的（β-硝基环丙基）膦酸盐的竞争性形成。由此形成的5-膦酰基异恶唑啉N-氧化物被还原为相应的5-膦酰基异恶唑啉。
• An Alternative to the Arbuzov Reaction: Generation and Transformation of α-Dialkyl-Substituted Methylphosphonate Carbanions via an SET Reduction Process
  作者：Li Zhang、Yewen Fang、Jianxun Shi

  DOI：10.1055/a-1959-2742

  日期：2023.3

  B-alkyl-9-borabicyclo[3.3.1]nonane (B-alkyl-9-BBN). Using the α-alkylethenylphosphonates as radical acceptors, visible-light-driven photocatalytic Giese-type and cyclopropanation reactions based on reductive radical-polar crossover have been successfully developed. The redox-neutral photocatalysis serves as a viable strategy for the preparation of various 1,1-dialkyl-substituted methylphosphonates and

  以 B-alkyl Suzuki 交叉偶联为策略，1-烷基取代的乙烯基膦酸酯可以通过钯催化的 α-phosphonovinyl tosylates 与 B-alkyl-9-borabicyclo[3.3.1]nonane (B-alkyl -9-BBN）。使用α-烷基乙烯基膦酸酯作为自由基受体，成功开发了基于还原性自由基-极性交叉的可见光驱动的光催化 Giese 型和环丙烷化反应。氧化还原中性光催化是制备各种 1,1-二烷基取代甲基膦酸酯和 1-烷基环丙基膦酸酯的可行策略。
• Nickel‐Catalyzed Asymmetric Hydrogenation of α‐Substituted Vinylphosphonates and Diarylvinylphosphine Oxides
  作者：Hanlin Wei、Hao Chen、Jianzhong Chen、Ilya D. Gridnev、Wanbin Zhang

  DOI：10.1002/anie.202214990

  日期：2023.2

  The first efficient Ni-catalyzed asymmetric hydrogenation of terminal olefins using H2 was developed, affording chiral ethylphosphine products with up to 99 % yield, 96 % ee and 1000 S/C (substrate/catalyst). The calculation and experimental mechanism study indicate that the two added hydrogen atoms of the product originate from H2 and the reaction proceeds through a NiII rather than Ni0 cyclic process

  开发了第一个使用 H 2对末端烯烃进行有效的镍催化不对称氢化反应，提供了高达 99% 收率、96% ee 和 1000 S/C（底物/催化剂）的手性乙基膦产物。计算和实验机理研究表明，产物中加入的两个氢原子来源于H 2，反应通过Ni II而不是Ni 0循环过程进行。
• Synthesis of 2-aziridinyl phosphonates by modified Gabriel–Cromwell reaction and their antibacterial activities
  作者：Özdemir Doğan、Hakan Babiz、Ayşe Gül Gözen、Songül Budak

  DOI：10.1016/j.ejmech.2011.03.037

  日期：2011.6

  A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.