N¹-dimethoxythiophosphoro-N¹-methylhydrazide | 80254-53-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: N¹-dimethoxythiophosphoro-N¹-methylhydrazide
• 英文别名: 1-methylphosphorohydrazidothioic acid O,O-dimethylester；1-dimethoxyphosphinothioyl-1-methylhydrazine
• CAS: 80254-53-1
• 化学式: C₃H₁₁N₂O₂PS
• 分子量: 170.172
• InChiKey: NOUZYQNFVZXLEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-羟基-2-氧代-2H-色烯-3-甲醛 、 N¹-dimethoxythiophosphoro-N¹-methylhydrazide 以 甲醇 为溶剂， 反应 24.0h， 以86%的产率得到(E)-3-{[(dimethoxythiophosphoryl)-methylhydrazono]methylene}-4-hydroxy-2H-1-benzopyran-2-one
  参考文献：
  名称：

  In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone

  摘要：

  The aim of this research was to examine chemical and biological properties of the products (4a-c/5a-c, 8b-c, 9a-b) of the reaction of methyl chromone-3-carboxylate (2), 3-fonnyl-4-hydroxycoumarin (3), 3-formylchromone (6) and chromone 3-carbonyl chloride (7) with phosphorus hydrazides (1a-c). For structure and keto-enol tautomerism analyses H-1, C-13, P-31 NNM spectroscopy was used. The ring transformation species (4a-c/5a--c) containing the coumarin ring (5a-c) were predominant in the solution. The chromone series 8b-c and 9a-b was obtained in reaction of phosphorus hydrazides (la-c) with 3-formylchromone (6) and chromone-3-carbonyl chloride (7). Alkylating activity of phosphorohydrazides of coumarin and chromone was determined with in vitro Preussmarm test (NBP test). Some of the compounds were examined towards antitumor and antibacterial activity. Compounds 4b-c/5b-c and 9a demonstrated in vitro antitumor activity against P388 leukemia. Antineoplastic activity of the compounds 4b/5b and 9a combined with methotrexate was showed using L1210 murine leukemia. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.06.004
• 作为产物：
  描述：

  二甲基硫代磷酰氯 、 甲基肼 以 氯仿 为溶剂， 反应 6.0h， 以85%的产率得到N¹-dimethoxythiophosphoro-N¹-methylhydrazide
  参考文献：
  名称：

  Reaction of methylhydrazine with dimethyl chlorothiophosphate

  摘要：

  The reaction of 2 equivalents of methylhydrazine with 1 equivalent of (MeO)2P(S)Cl at 0-degrees-C produced the phosphorus hydrazide (MeO)2P(S)NMeNH2 1 in good yield. However, at 25-degrees-C a mixture of three products was obtained according to H-1 and P-31 NMR spectra. The pure individual components were separated by column chromatography. Proton and P-31 NMR analysis revealed them to be 1, (MeO)2P(S)(NMeNH)(S)P(OMe)2 2 and (MeO)2P(S)NHNHMe 3. During the chromatographic separation of 1-3 another component was also eluted in 5-8% yield, H-1, P-31 NMR and FAB mass spectrometric analysis of which indicated it to be (MeO)2P(S)(NMeNH)(O)P(OMe)Me4. New synthetic strategies to produce 2 in good yields are also described.

  DOI：

  10.1039/dt9940001581

文献信息

• Wang, Meifang; Volkert, Eric W.; Sing, Prahlad R., Inorganic Chemistry, 1994, vol. 33, # 6, p. 1184 - 1187
  作者：Wang, Meifang、Volkert, Eric W.、Sing, Prahlad R.、Katti, Kavita K.、Lusiak, Przemyslaw、Katti, Kattesh V.、Barnes, Charles L.

  DOI：——

  日期：——
• X-ray investigations of benzopyran derivatives substituted at position 3
  作者：A. J. Rybarczyk、T. A. Olszak、M. Małecka、J. Nawrot-Modranka

  DOI：10.1107/s0108270199004734

  日期：1999.8.15

  The structures of two isomeric compounds, (E)-3-[2-( dimethoxythiophosphoryl)-2-methylhydrazino]methylidene}-3,4-dihydro-2H-1-benzopyran-2,4-dione, C13H15N2O5PS, and 3-[2-(dimethoxythiophosphoryl)-2-methylhydrazino] carbonyl}-3,4-dihydro-4H-1-benzopyran-4-one, C13H15N2O5PS, have been determined from X-ray data and compared. The benzopyran moieties of both molecules are planar. Extra six-membered rings are formed by N-H ... O hydrogen bonds. The geometry around the P atoms is tetrahedral, slightly deformed to trigonal pyramidal.
• Lusiak Przemyslaw, Singh Prahlad R., Katti Kattesh V., J. Chem. Soc. Dalton Trans, (1994) N 10, S 1581-1584
  作者：Lusiak Przemyslaw, Singh Prahlad R., Katti Kattesh V.

  DOI：——

  日期：——