1-diethoxyphosphoryl-4-methyl-1-methoxy-2,3-pentadiene | 126307-80-0

• 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: 1-diethoxyphosphoryl-4-methyl-1-methoxy-2,3-pentadiene
• 英文别名: O,O-diethyl-1-methoxy-2,3-pentadiene-2-phosphonate；diethyl (1-methoxy-4-methylpenta-2,3-dien-2-yl)phosphonate
• CAS: 126307-80-0
• 化学式: C₁₁H₂₁O₄P
• 分子量: 248.259
• InChiKey: LYHCNYCGVRTPST-UHFFFAOYSA-N

物化性质

• 沸点：
  332.3±35.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-diethoxyphosphoryl-4-methyl-1-methoxy-2,3-pentadiene 在 copper(l) iodide 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2,2-dimethyl-3-iodo-4-(diethylphosphono)-2,5-dihydrofuran
  参考文献：
  名称：

  Interaction of an allene with polyvalent iodine derivatives. Preparation, x-ray molecular structure, and some reactions of phenyl(2,2-dimethyl-4-(diethylphosphono)-2,5-dihydro-3-furyl)iodonium salts

  摘要：

  Allene 1 reacts with PhIO/BF3.Et2O or PhIF2/BF3.Et2O in CH2Cl2 at -60-degrees-C with the formation of novel phenyldihydrofuryliodonium salts 2. Molecular structures for both products 2a,b are determined by X-ray analysis. Iodonium perchlorate 2b reacts with the anionic nucleophiles (NaN3, NaOCH3, NaOC2H5, CuI/KI) to give the corresponding products of the vinylic nucleophilic substitution (6a-e) of the iodobenzene moiety. However, analogous reaction of 2b with Ph3P gives an unexpected iodide 6e as the major product, along with the usual product of nucleophilic substitution (6d). This result is rationalized by a nucleophilic attack of Ph3P on the iodine atom of the iodonium salt 2b followed by two alternative paths for subsequent ligand coupling.

  DOI：

  10.1021/jo00034a043
• 作为产物：
  描述：

  二乙基亚磷酰氯 、 5-methoxy-2-methyl-3-pentyn-2-ol 、 三乙胺 以61%的产率得到
  参考文献：
  名称：

  BREL, V. K.;ABRAMKIN, E. V.;MARTYNOV, I. V.;IONIN, B. I., IZV. AN CCCP. CEP. XIM.,(1989) N2, S. 2736-2740

  摘要：

  DOI：

文献信息

• 4-Alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2-oxaphosphole 2-Oxides: Synthesis and 1,3-Cycloaddition
  作者：Valery K. Brel、Ekaterina P. Alekseychuk、Oleg I. Artyushin、Lada V. Anikina

  DOI：10.1055/s-0040-1720922

  日期：2022.4

  three-steps synthesis of a new class of organic azides with a 1,2-oxaphospholene carbon skeleton has been developed. The series of obtained 4-alkyl-3-azidomethyl-2-ethoxy-2,5-dihydro-5H-1,2-oxaphosphole 2-oxides were utilized in the 1,3-cycloaddition with alkyl 2-[1-(propyn-2-yl)-1H-indol-3-yl]-2-oxoacetates for the synthesis of conjugates, which are potentially active cytostatics.

  从磷酸化的丙二烯开始，开发了一种具有 1,2-氧杂磷烯碳骨架的新型有机叠氮化物的三步合成。该系列得到的4-烷基-3-叠氮基甲基-2-乙氧基-2,5-二氢-5- ħ -1,2- oxaphosphole 2氧化物中使用了1,3-环加成与烷基2- [1-（ propyn-2-yl)-1 H -indol-3-yl]-2-oxoacetates 用于合成偶联物，这是潜在的活性细胞抑制剂。
• Alkenylsulfenylchlorides : Synthesis and AdE reactions of 2-alkoxy-2-oxo-3-R-4-chlorothio-1,2-oxaphosphol-3-enes
  作者：Igor V. Alabugin、Valery K. Brel、Anatoly N. Chekhlov、Nikolai S. Zefirov、Peter J. Stang

  DOI：10.1016/0040-4039(94)88301-7

  日期：1994.10

  Synthesis of titled representatives of alkenylsulfenylchlorides by the reaction of SCl2 with allenes 1 and 2 is described and their AdE reactions with some model olefins are discussed.

  描述了通过SCl 2与丙二烯1和2的反应合成链烯基磺酰氯的标题代表，并讨论了它们与某些模型烯烃的Ad E反应。
• Functionally substituted allene phosphonates and their transformation products. 2. Reaction of phosphorus-containing 1-methoxy-2,3-alkadienes with organomagnesium compounds
  作者：V. K. Brel'、E. V. Abramkin

  DOI：10.1007/bf00961506

  日期：1990.8

  3-Alkyl-1,3-alkadienylphosphonates were obtained by the reaction of phosphorus-containing 1-methoxy-2,3-alkadienes with a Grignard reagent.
• Alabugin, I. V.; Brel', V. K.; Zefirov, N. S., Russian Journal of General Chemistry, 1993, vol. 63, # 10.2, p. 1656 - 1657
  作者：Alabugin, I. V.、Brel', V. K.、Zefirov, N. S.

  DOI：——

  日期：——
• SO3-Mediated reaction of phenylselenenylamide with 1,2-alkadienylphosphonates
  作者：I. V. Alabugin、V. K. Brei、N. V. Zyk、N. S. Zefirov

  DOI：10.1007/bf01435823

  日期：1996.3

  SO3-Mediated reaction of N,N-diethylphenylselenenylamide with 1,2-alkadienyl-phosphonates under conditions of generation of weak electrophilic species results in the formation of cyclization products involving phosphoryl oxygen.