O-phenyl chloromethylisocyanatothioxophosphonate | 178437-40-6

• 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: O-phenyl chloromethylisocyanatothioxophosphonate
• 英文别名: phenyl (chloromethyl)phosphonoisocyanatidate；phenyl (chloromethyl)isocyanatophosphonate；phenyl chloromethylphosphonoisocyanatidate；phenyl chloromethylisocyanatophosphonate；Isocyanato-chlormethylphosphonsaeure-phenylester；Phosphonisocyanatidic acid, (chloromethyl)-, phenyl ester；[chloromethyl(isocyanato)phosphoryl]oxybenzene
• CAS: 178437-40-6
• 化学式: C₈H₇ClNO₃P
• 分子量: 231.575
• InChiKey: KOWLWUSMUGGGGT-UHFFFAOYSA-N

物化性质

• 沸点：
  105-110 °C(Press: 0.08 Torr)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-phenyl chloromethylisocyanatothioxophosphonate 在 氨 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 8.0h， 生成 4-Oxo-4-phenoxy-4,5-dihydro-4λ⁵-[1,3,4]oxazaphosphol-2-ylamine
  参考文献：
  名称：

  摘要：

  Bis(chloromethyl)phosphinic (-phosphinothioic) iso(thio)cyanates add secondary amines to form N-phosphorylated (thio)ureas, which cyclize in the presence of a base to 1,3,4lambda(5)-oxaza(thiaza)phospholines. Phosphorylated ureas obtained by addition of ammonia and primary amines to chloromethylphosphonic (-phosphinic) isocyanates cyclize to give 1,4,2-diazaphospholidines or 1,3,4-oxazaphospholines. Prototropic transformations in the series of 1,3,4lambda(5)-oxazaphospholines were revealed; the electronic and steric structures of the tautomers were studied. Chi oromethylphosphonothioic (-phosphinothioic) isothiocyanates add primary amines to give 1,3,4lambda(5)-thiazaphospholines.

  DOI：

  10.1023/a:1020746615033
• 作为产物：
  描述：

  草酰氯 、 phenyl P-(chloromethyl)phosphonamidate 以 四氯化碳 为溶剂， 生成 O-phenyl chloromethylisocyanatothioxophosphonate
  参考文献：
  名称：

  Shokol,V.A. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 2146 - 2149

  摘要：

  DOI：

文献信息

• Reaction of chloromethyliso(thio)cyanato(thio)phosphonates(-phosphinates) with phenol, ethanol, and thiols
  作者：N. A. Khailova、R. Kh. Bagautdinova、A. A. Shaimardanova、N. E. Krepysheva、M. A. Pudovik、G. A. Chmutova、N. M. Azancheev、R. Z. Musin、A. N. Pudovik

  DOI：10.1007/s11176-005-0006-7

  日期：2004.9

  (Chloromethyl)isocyanatophosphonates(-phosphinates) take up phenol to form carbamates whose β-cleavage gives rise to phenyl (chloromethyl)phosphonates(-phosphinates). (Chloromethyl)(thio)phosphinic-(phosphonic) isothiocyanates react with phenol at 20°C in the absence of catalyst to afford phenyl phosphinates(-phosphonates). (Alkylsulfanyl)carbamates formed by addition of thiols to (chloromethyl)iso(thio)cyanastophosphonates(-phosphinates) under the action of an equimolar amount of triethylamine undergo cyclization into 1,3,4-oxaza(thiaza)phospholines.

  氯甲基异氰酸磷酸酯（膦酸酯）与酚反应生成氨基甲酸酯，其β-断裂产生苯基氯甲基磷酸酯（膦酸酯）。氯甲基硫代磷酸（膦酸）异硫氰酸酯在无催化剂下于20°C与酚反应生成苯基膦酸酯（磷酸酯）。在三乙胺等摩尔量的作用下，硫醇与氯甲基异（硫）氰酸磷酸酯（膦酸酯）加成形成的烷硫基氨基甲酸酯发生环化生成1,3,4-氧杂（硫杂）磷杂环。
• Reaction of Phosphoric (Phosphonic) Acids Amides with Chloromethyliso(thio)cyanatophosphonates (-phosphinates). Synthesis of 1,3,4-Oxaza(thiaza)phospholines
  作者：N. A. Khailova、A. A. Shaimardanova、M. A. Pudovik、N. M. Aznacheev、A. N. Pudovik

  DOI：10.1007/s11178-006-0006-z

  日期：2005.11

  Addition of phosphoric (phosphonic) acids amides to chloromethyliso(thio)cyanatophosphonates (-phosphinates) gave rise to diphosphorylated ureas or thioureas that under effect of bases underwent cyclization into 1,3,4-oxaza(thiaza)phospholines.

  将磷酸（膦酸）酰胺添加到氯甲基异（硫）氰基膦酸盐（-膦酸盐）中会产生二磷酸化的脲类或硫脲类化合物，在碱的作用下环化成 1,3,4-氧氮杂（硫杂）膦脂。
• Khailova; Shaimardanova; Pudovik, Russian Journal of General Chemistry, 2000, vol. 70, # 2, p. 314 - 316
  作者：Khailova、Shaimardanova、Pudovik、Pudovik

  DOI：——

  日期：——
• Experimental and theoretical investigation of intramolecular transformations of silicon-containing (haloalkyl)phosphorylated ureas and acylamides
  作者：M. A. Pudovik、G. A. Chmutova、L. K. Kibardina、S. A. Terent’eva、R. Kh. Bagautdinova、N. A. Khailova、R. M. Kamalov、A. N. Pudovik

  DOI：10.1134/s1070363206030078

  日期：2006.3

  Silicon-containing chloromethylphosphorylated ureas undergo transformation involving evolution of chlorotrimethylsilane and formation of 1,3,4-oxazaphospholes. Their analogs, silicon-containing phosphorylated acylamides, transform in another way, viz. by beta-cleavage to form the corresponding siloxyphosphonates. Quantum-chemical investigation of thermodynamic characteristics of these processes was carried out.
• Reaction of (chloromethyl)phosphonic(-phosphinic) iso(thio)cyanates with alcohols and (α-hydroxyalkyl)phosphonates
  作者：N. A. Khailova、R. Kh. Bagautdinova、M. A. Pudovik、R. Z. Musin、N. M. Azancheev、Sh. K. Latypov、T. A. Zyablikova、O. N. Kataeva、I. A. Litvinov、E. A. Evgen’eva、A. N. Pudovik

  DOI：10.1134/s107036320603008x

  日期：2006.3

  Alcohols and alpha-hydroxyphosphonates undergo the addition to (chloromethyl)phosphonic(-phosphinic) iso(thio)cyanates, yielding phosphorylated (thio)urethanes. The latter undergo cyclization to form, depending on their structure, saturated or unsaturated five-membered P,N,O,S-containin-heterocycles.