Dimethyl 1-formylpropylphosphonate | 67445-34-5

• 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: Dimethyl 1-formylpropylphosphonate
• 英文别名: Dimethyl 1-formylethylphosphonate；Phosphonic acid, (1-methyl-2-oxoethyl)-, dimethyl ester；2-dimethoxyphosphorylpropanal
• CAS: 67445-34-5
• 化学式: C₅H₁₁O₄P
• 分子量: 166.114
• InChiKey: ZSOXFOYBWFQGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 1-formylpropylphosphonate 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 膦酸,(2-羟基-1-甲基乙基)-,二甲基酯
  参考文献：
  名称：

  Synthesis of Dimethyl (1-Nitromethylalkyl)phosphonates and their Conversion to Dimethyl (1-Formylalkyl)phosphonates by Oxidation with Ozone

  摘要：

  膦酸二甲酯与硝基烯烃发生加成反应，生成（1-硝甲基烷基）膦酸二甲酯，通过臭氧氧化，可成功转化为（1-甲酰基烷基）膦酸二甲酯。

  DOI：

  10.1055/s-1987-27846
• 作为产物：
  描述：

  Dimethyl 1-(nitromethyl)ethylphosphonate 生成 Dimethyl 1-formylpropylphosphonate
  参考文献：
  名称：

  Synthesis of Dimethyl (1-Nitromethylalkyl)phosphonates and their Conversion to Dimethyl (1-Formylalkyl)phosphonates by Oxidation with Ozone

  摘要：

  膦酸二甲酯与硝基烯烃发生加成反应，生成（1-硝甲基烷基）膦酸二甲酯，通过臭氧氧化，可成功转化为（1-甲酰基烷基）膦酸二甲酯。

  DOI：

  10.1055/s-1987-27846

文献信息

• Preparation of Dimethyl (1-Formylalkyl)phosphonates<i>via</i>Singlet Oxygen Adducts
  作者：Mitsuji Yamashita、Hiroyuki Nomoto、Hiroyuki Lmoto

  DOI：10.1055/s-1987-28057

  日期：——

  The nitro group of dimethyl (1-nitromethylalkyl)phosphonates is conveniently converted into a formyl group by reaction with singlet oxygen to give dimethyl (1-formylalkyl)phosphonates. (1-Formylbutyl)diphenylphosphine oxide is prepared by the same reaction.

  1-硝甲基烷基）膦酸二甲酯的硝基通过与单线态氧反应转化为甲酰基，从而得到（1-甲酰基烷基）膦酸二甲酯。 (1-甲酰基丁基)二苯基氧化膦也是通过同样的反应制备的。
• Manufacture of .alpha.-formylethanephosphonic acid esters
  申请人：BASF Aktiengesellschaft

  公开号：US04198354A1

  公开（公告）日：1980-04-15

  .alpha.-Formylethane-phosphonic acid esters are manufactured by reacting vinylphosphonic acid esters with carbon monoxide and hydrogen in the presence of conventional rhodium-containing hydroformylation catalysts. The reaction is carried out at from 50.degree. to 180.degree. C. and at pressures from 20 to 1,500 bars. The products are intermediates for the synthesis of insecticidally active phosphoric acid ester derivatives.

  .alpha.-甲酰乙烯基膦酸酯是通过在常规含铑的氢甲酰化催化剂存在下，将乙烯基膦酸酯与一氧化碳和氢反应制得。反应在50℃至180℃和20至1,500巴的压力下进行。产品是合成杀虫活性磷酸酯衍生物的中间体。
• One Step Selective Counterion Dependent Formation of Conjugated Chiral N-Sulfinylimines from Aldehydes
  作者：Jeffrey R. Groch、Nicholas R. Lauta、Jon T. Njardarson

  DOI：10.1021/acs.orglett.2c04102

  日期：2023.1.20

  We report a detailed study on the synthesis and aldehyde vinylogation applications of chiral N-sulfinyl imine phosphonate reagents. Two complementary scalable reagent routes, from trialkyl phosphites and methyl phosphonates, respectively, are presented. This reagent class enables significant streamlining in synthesis of conjugated Ellman imines from aldehydes, which can now be accomplished in a single

  我们报告了关于手性 N-亚磺酰亚胺膦酸酯试剂的合成和醛乙烯基化应用的详细研究。介绍了两种互补的可扩展试剂路线，分别来自亚磷酸三烷基酯和膦酸甲酯。该试剂类别可显着简化从醛类合成共轭埃尔曼亚胺的过程，与更经典的基于氧化还原的四步法相比，现在只需一步即可完成。醛乙烯化优化揭示了显着的抗衡离子效应和意想不到的竞争反应挑战，需要解决这些挑战才能实现高产率。
• Ismailov, V. M.; Moskva, V. V.; Guseinov, F. I., Journal of general chemistry of the USSR, 1986, vol. 56, # 9, p. 1768 - 1771
  作者：Ismailov, V. M.、Moskva, V. V.、Guseinov, F. I.、Zykova, T. V.、Sadyakov, I. S.

  DOI：——

  日期：——
• Hydroformylation Reactions with Recyclable Rhodium-Complexed Dendrimers on a Resin
  作者：Shui-Ming Lu、Howard Alper

  DOI：10.1021/ja0303384

  日期：2003.10.1

  Rhodium-complexed dendrimers supported on a resin were evaluated as catalysts for the hydroformylation of aryl olefins and vinyl esters. The results showed the reactions proceeded very efficiently at room temperature with excellent yields. Outstanding selectivity for the branched aldehydes was also observed in all cases. The dendritic catalysts can be recycled by simple filtration and reused even up to the tenth cycle without loss of activity and selectivity. These results represent a dramatic improvement over those previously described for rhodium-catalyzed (dendrimer and nondendrimer based) hydroformylation reactions.