bis(chloromethyl)phosphinothioic isothiocyanate | 165130-94-9

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机硫代磷化合物
• 英文名称: bis(chloromethyl)phosphinothioic isothiocyanate
• 英文别名: bis(chloromethyl)thiophosphinic isothiocyanate；bis(chloromethyl)-isothiocyanato-sulfanylidene-λ5-phosphane
• CAS: 165130-94-9
• 化学式: C₃H₄Cl₂NPS₂
• 分子量: 220.083
• InChiKey: GMVIHOBGEGNCHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三甲基硅烷基二乙胺 、 bis(chloromethyl)phosphinothioic isothiocyanate 以 乙醚 为溶剂， 反应 24.0h， 以74%的产率得到4-chloromethyl-2-diethylamino-Δ²-1,3,4λ⁵-thiazaphospholine 4-sulfide
  参考文献：
  名称：

  Pudovik, M. A.; Al'myanova, R. Kh.; Kamalov, R. M., Russian Journal of General Chemistry, 1995, vol. 65, # 2.2, p. 292

  摘要：

  DOI：
• 作为产物：
  描述：

  bis-chloromethyl-phosphinothioic acid 以83%的产率得到
  参考文献：
  名称：

  Kamalow R. M., Almjanowa R. Kh., Pudowik M. A., Zh. obshh. khimii, 64 (1994) N 11, S 1781-1783

  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。
• Development of the Synthesis Methods of Polyheterophosphacyclanes with Endocyclic P-C Bond on the Basis of Functionalized Alkylphosphonates (-Phosphinates)
  作者：Mikhael A. Pudovik、Natalia A. Khailova、Roza Kh. Bagautdinova、Svetlana A. Terent'eva、Ludmila K. Kibardina、Olga N. Kataeva、Vladimir A. Alfonsov

  DOI：10.1080/10426500701761151

  日期：2008.1.14

  We developed a new approach to the synthesis of saturated and unsaturated phosphoruselementocontaining heterocycles was developed; we based it on the addition reactions of various proton nucleophiles (amines, silylamines, alcoholes, mercaptanes, aminoalkylphosphonates, phosphines, CH-acides, etc.) to the halogenmethylphosphonylated isocyanates or isothiocyanates. Intermediate compounds of these reactions

  我们开发了一种合成饱和和不饱和含磷元素杂环的新方法；我们基于各种质子亲核试剂（胺、甲硅烷胺、醇、硫醇、氨基烷基膦酸酯、膦、CH-​​酸等）与卤甲基膦酰化异氰酸酯或异硫氰酸酯的加成反应。这些反应的中间化合物（磷酸化脲、硫脲、氨基甲酸酯、硫脲烷、酰胺等）很容易转化为含磷的环状结构。
• Pudovik; Krepysheva; Al'myanova, Russian Journal of General Chemistry, 1996, vol. 66, # 3, p. 349 - 352
  作者：Pudovik、Krepysheva、Al'myanova、Kamalov、Pudovik

  DOI：——

  日期：——
• ——
  作者：N. A. Khailova、N. E. Krepysheva、G. M. Saakyan、R. Kh. Bagautdinova、A. A. Shaimardanova、T. A. Zyablikova、N. M. Azancheev、I. A. Litvinov、A. T. Gubaidullin、V. V. Zverev、M. A. Pudovik、A. N. Pudovik

  DOI：10.1023/a:1020746615033

  日期：——

  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.