diethyl (1-benzamido-2,2-dichlorovinyl)phosphonate | 50966-09-1

• 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: diethyl (1-benzamido-2,2-dichlorovinyl)phosphonate
• 英文别名: (1-benzoylamino-2,2-dichloro-vinyl)-phosphonic acid diethyl ester；N-(1-Diethoxyphosphinyl-2.2-dichlorvinyl)benzamid；Phosphonic acid, [1-(benzoylamino)-2,2-dichloroethenyl]-, diethyl ester；N-(2,2-dichloro-1-diethoxyphosphorylethenyl)benzamide
• CAS: 50966-09-1
• 化学式: C₁₃H₁₆Cl₂NO₄P
• 分子量: 352.154
• InChiKey: YMSNEBSFIYAGSF-UHFFFAOYSA-N

物化性质

• 沸点：
  442.1±45.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (1-benzamido-2,2-dichlorovinyl)phosphonate 在 五氯化磷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 3-(dichloromethylidene)-2-methoxy-5-phenyl-1,4,2λ5-oxazaphosphole 2-oxide
  参考文献：
  名称：

  Lobanov, O. P.; Drach, B. S., Journal of general chemistry of the USSR, 1982, vol. 52, # 5, p. 980 - 988

  摘要：

  DOI：
• 作为产物：
  描述：

  sodium ethanolate 、 azlactone of (1-benzamido-2,2-dichlorovinyl)phosphonochloridic acid 以 乙醇 为溶剂， 反应 4.5h， 以90%的产率得到diethyl (1-benzamido-2,2-dichlorovinyl)phosphonate
  参考文献：
  名称：

  Lobanov, O. P.; Drach, B. S., Journal of general chemistry of the USSR, 1982, vol. 52, # 5, p. 980 - 988

  摘要：

  DOI：

文献信息

• Reaction of diethyl esters of 1-acylamino-2,2-dichlorovinylphosphonic acids and their analogs with the Lawesson’s reagent
  作者：S. V. Popil’nichenko、K. M. Kondratyuk、R. N. Solomyannyi、V. S. Brovarets

  DOI：10.1134/s1070363210100105

  日期：2010.10

  Diethyl esters of 1-acylamino-2,2-dichlorovinylphosphonic acids and their analogs upon heating with the Lawesson’s reagent are converted into the earlier unknown substituted 1,3-thiazol-4-ylthiophosphonates in high yields.

  将1-酰基氨基-2，2-二氯乙烯基膦酸的二乙酯及其类似物在与Lawesson试剂一起加热后，可以高产率转化为更早的未知取代的1,3-噻唑-4-基硫代膦酸酯。
• Transformations of Acylation Products of Functionally 4-Substituted 2-Alkyl(aryl)-5-hydrazino-1,3-oxazoles into 1,3,4-Oxadiazole Derivatives
  作者：A. V. Golovchenko、S. G. Pil’o、V. S. Brovarets、A. N. Chernega、B. S. Drach

  DOI：10.1007/s11176-005-0244-8

  日期：2005.3

  Acylation products of 2-aryl-5-hydrazino-4-X-1,3-oxazoles [X = C(O)OAlk, P(O)(OAlk)2], when heated in acetic acid or ethanol, undergo recyclization and transform into the derivatives of 1,3,4-oxadiazol-2-ylglycine or its phosphonyl analog. A similar rearrangement also occurs in the reactions of 2-alkyl(aryl)-5-hydrazino-1,3-oxazole-4-carbonitriles with carboxylic acid chlorides in pyridine, but it is accompanied by additional cyclization involving the amide residue and nitrile group, yielding 2-(5-amino-1,3-oxazol-4-yl)-1,3,4-oxadiazole derivatives.

  2-芳基-5-肼基-4-X-1,3-噁唑的酰化产物 [X = C(O)OAlk, P(O)(OAlk)2] 在加热于醋酸或乙醇时，发生重环化，转化为 1,3,4-噁二唑-2-基甘氨酸或其磷酸酯类似物的衍生物。在与吡啶中的羧酸氯化物反应时，2-烷基（芳基）-5-肼基-1,3-噁唑-4-腈也发生类似的重排，但伴随有额外的环化，涉及酰胺残基和腈基，生成 2-(5-氨基-1,3-噁唑-4-基)-1,3,4-噁二唑衍生物。
• ——
  作者：V. S. Brovarets、R. N. Vydzhak、S. G. Pil'o、K. V. Zyuz'、B. S. Drach

  DOI：10.1023/a:1013982122431

  日期：——

  Treatment of 1-phosphorylated 2,2-dichloroethenylcarboxamides with excess hydrazine hydrate gives in high yields phosphorylated derivatives of 2-alkyl(aryl)-5-hydrazinooxazoles containing the P(O)(OCH3)(2), P(O)(OC2H5)(2), and P+(C6H5)3ClO(4)(-) groups in the 4-position of the ring. The presence of the hydrazine group in these oxazole derivatives was confirmed not only by the spectral data, but also by the reactions with p-toluic aldehyde, p-toluic chloride, and phenyl isothiocyanate.
• Drach,B.S.; Lobanov,O.P., Journal of general chemistry of the USSR, 1974, vol. 44, p. 2730
  作者：Drach,B.S.、Lobanov,O.P.

  DOI：——

  日期：——
• ——
  作者：S. G. Pil'o

  DOI：10.1023/a:1023333011230

  日期：——

  Enamides of the general formula Cl2C=C(X)NHCOR1, where X = CN, COOAlk, CONH2, P(O)(OEt)(2), P(O)Ph-2, PPh3 Cl-, were treated in succession with alkane- or arenethiols and silver carbonate to obtain 5-alkyl(aryl)thio-2-R-1-4-X-1,3-oxazoles with high selectivity. The latter were converted into the corresponding sulfonyl derivatives. Unlike 2-acylamino-3,3-dichloroacrylonitriles which react with sodium hydrogen sulfide in a nonselective fashion, reactions of derivatives like Cl(ArS)C=C(CN)NHCOR1 with NaHS lead to hitherto unknown 5-arylthio-4-thiocarbamoyl-2-R-1-1,3-oxazoles whose structure was confirmed both by spectral methods and by cyclocondensation with bromoacetophenone according to Hantzsch. Heating of some 2-aryl-5-mercapto-4-X-1,3-oxazoles with benzenethiols results in recyclization into the corresponding 2,4-disubstituted 5-arylthio-1,3-thiazoles, presumably due to prototropic tautomerism in the 5-mercapto-oxazole fragment.