N-(diisopropoxyphosphoryl) morpholine-4-thiocarboxamide | 902146-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(diisopropoxyphosphoryl) morpholine-4-thiocarboxamide
• 英文别名: N-(diisopropoxyphosphoryl)morpholine-4-thiocarboxamide；(morpholine-N-yl)-C(S)-N(H)-P(O)(OiPr)2；morpholine-N-yl-CSNHPO(O-iPr)2；N-di(propan-2-yloxy)phosphorylmorpholine-4-carbothioamide
• CAS: 902146-70-7
• 化学式: C₁₁H₂₃N₂O₄PS
• 分子量: 310.354
• InChiKey: XPOPEDSRAGOAPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(diisopropoxyphosphoryl) morpholine-4-thiocarboxamide 、 二(氰基苯)二氯化钯 在 KOH 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 以52%的产率得到cis-1,5-O,S-[Pd((morpholine-N-yl)-C(S)-N-P(O)(OiPr)2)2]
  参考文献：
  名称：

  The influence of the intramolecular hydrogen bond on the 1,3-N,S- and 1,5-O,S-coordination of N-phosphoryl-N′-(R)-thioureas with Ni(ii) and Pd(ii)

  摘要：

  通式为 R1âN(H)âC(S)âN(H)âP(O)(OiPr)2 (HA) 的 N-磷酸化硫脲的钾盐与 NiII 和 PdII 阳离子反应生成 [MA2] 螯合物（M = NiII，R1 = p-MeOC6H4、p-BrC6H4、t-Bu、c-Hex；M = PdII，R = iPr）。在 NiII 和 PdII 复合物中，金属中心都位于由 CS 硫原子和两个去质子化配体 Aâ 的 PâN 氮原子形成的方形平面 N2S2 环境中。[PdB2]配合物中的钯二原子与通式为 R2âC(S)âN(H)âP(O)(OiPr)2 (HB)（R2 = Et2N，吗啉-N-基）的去质子化硫脲以方形平面的方式由 CS 硫原子和两个阴离子配体的 PO 氧原子配位。通过 X 射线衍射阐明了四种配合物 [M(A-N,S)2]（M = NiII，R1 = p-MeOC6H4、p-BrC6H4、t-Bu；M = PdII，R1 = iPr）和式为 [Pd(B-O,S)2]（R2 = 吗啉-N-基）的 1,5-O,S-螯合钯（II）的分子结构。

  DOI：

  10.1039/b702896b
• 作为产物：
  描述：

  吗啉 、 diisopropoxyphosphoryl isothiocyanate 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到N-(diisopropoxyphosphoryl) morpholine-4-thiocarboxamide
  参考文献：
  名称：

  Specific Features of the Structure of Chelate Complexes of N-Thiocarbamoylamidophosphates with Zn(II) and Cd(II) Cations

  摘要：

  N-硫代氨基甲酰氨基磷酸钾盐的反应 RC(S)NHP(O)(OPr-i)2X [X = PhNH, p-MeOPhNH, p-BrPhNH, i-PrNH, t-BuNH, Et2N, C5H10N, OC4H8N, C6H11NH] 与 Zn(II) 阳离子生成组成为 Zn(L-O,S)2 的络合物。 Cd(II) 配合物由于其水解不稳定性而无法在类似条件下分离。硫脲 (X = PhNH, p-MeOPhNH) 与乙酸 Cd(II) 在 DMF 中反应，得到组成为 Cd(DMF)2L2 的稳定溶剂化配合物。通过IR、1H和31P NMR光谱以及EI和ESI质谱研究了所得化合物的结构。

  DOI：

  10.1007/s11176-006-0014-2

文献信息

• The influence of the intramolecular hydrogen bond on the 1,3-N,S- and 1,5-O,S-coordination of N-phosphoryl-N′-(R)-thioureas with Ni(ii) and Pd(ii)
  作者：Felix D. Sokolov、Sergey V. Baranov、Damir A. Safin、F. Ekkehardt Hahn、Maria Kubiak、Tania Pape、Maria G. Babashkina、Nail G. Zabirov、Joanna Galezowska、Henryk Kozlowski、Rafael A. Cherkasov

  DOI：10.1039/b702896b

  日期：——

  Reaction of the potassium salts of N-phosphorylated thioureas of common formula R1–N(H)–C(S)–N(H)–P(O)(OiPr)2 (HA) with NiII and PdII cations leads to [MA2] chelate complexes (M = NiII, R1 = p-MeOC6H4, p-BrC6H4, t-Bu, c-Hex; M = PdII, R = iPr). In both the NiII and PdII complexes, the metal center is found in a square-planar N2S2 environment formed by the CS sulfur atoms and the P–N nitrogen atoms of two deprotonated ligands A−. The PdII atoms in [PdB2] complexes with deprotonated thioureas of common formula R2–C(S)–N(H)–P(O)(OiPr)2 (HB) (R2 = Et2N, morpholine-N-yl) are coordinated in a square-planar fashion by the CS sulfur atoms and the PO oxygen atoms of two anionic ligands. Molecular structures of four complexes [M(A-N,S)2] (M = NiII, R1 = p-MeOC6H4, p-BrC6H4, t-Bu; M = PdII, R1 = iPr) and the palladium(II) 1,5-O,S-chelate of formula [Pd(B-O,S)2] (R2 = morpholine-N-yl) were elucidated by X-ray diffraction.

  通式为 R1âN(H)âC(S)âN(H)âP(O)(OiPr)2 (HA) 的 N-磷酸化硫脲的钾盐与 NiII 和 PdII 阳离子反应生成 [MA2] 螯合物（M = NiII，R1 = p-MeOC6H4、p-BrC6H4、t-Bu、c-Hex；M = PdII，R = iPr）。在 NiII 和 PdII 复合物中，金属中心都位于由 CS 硫原子和两个去质子化配体 Aâ 的 PâN 氮原子形成的方形平面 N2S2 环境中。[PdB2]配合物中的钯二原子与通式为 R2âC(S)âN(H)âP(O)(OiPr)2 (HB)（R2 = Et2N，吗啉-N-基）的去质子化硫脲以方形平面的方式由 CS 硫原子和两个阴离子配体的 PO 氧原子配位。通过 X 射线衍射阐明了四种配合物 [M(A-N,S)2]（M = NiII，R1 = p-MeOC6H4、p-BrC6H4、t-Bu；M = PdII，R1 = iPr）和式为 [Pd(B-O,S)2]（R2 = 吗啉-N-基）的 1,5-O,S-螯合钯（II）的分子结构。
• Specific Features of the Structure of Chelate Complexes of N-Thiocarbamoylamidophosphates with Zn(II) and Cd(II) Cations
  作者：F. D. Sokolov、D. A. Safin、N. G. Zabirov、P. V. Zotov、R. A. Cherkasov

  DOI：10.1007/s11176-006-0014-2

  日期：2005.12

  The reaction of potassium salts of N-thiocarbamoylamidophosphates RC(S)NHP(O)(OPr-i)2X [X = PhNH, p-MeOPhNH, p-BrPhNH, i-PrNH, t-BuNH, Et2N, C5H10N, OC4H8N, C6H11NH] with Zn(II) cation gives complexes of the composition Zn(L-O,S)2. The Cd(II) complexes could not be isolated under analogous conditions because of their hydrolytic lability. The reaction of thioureas (X = PhNH, p-MeOPhNH) with Cd(II) acetate in DMF provides stable solvato complexes of the composition Cd(DMF)2L2. The structure of the resulting compounds was studied by means of IR, 1H, and 31P NMR spectroscopy and EI and ESI mass spectrometry.

  N-硫代氨基甲酰氨基磷酸钾盐的反应 RC(S)NHP(O)(OPr-i)2X [X = PhNH, p-MeOPhNH, p-BrPhNH, i-PrNH, t-BuNH, Et2N, C5H10N, OC4H8N, C6H11NH] 与 Zn(II) 阳离子生成组成为 Zn(L-O,S)2 的络合物。 Cd(II) 配合物由于其水解不稳定性而无法在类似条件下分离。硫脲 (X = PhNH, p-MeOPhNH) 与乙酸 Cd(II) 在 DMF 中反应，得到组成为 Cd(DMF)2L2 的稳定溶剂化配合物。通过IR、1H和31P NMR光谱以及EI和ESI质谱研究了所得化合物的结构。
• Monodentate S-vs. bidentate 1,5-O,S-coordination of N-phosphoryl-N′-(R)-thioureas with Pd(II)
  作者：Damir A. Safin、Felix D. Sokolov、Łukasz Szyrwiel、Sergey V. Baranov、Maria G. Babashkina、Timur R. Gimadiev、Henryk Kozlowski

  DOI：10.1016/j.poly.2008.03.012

  日期：2008.6

  Reaction of N-phosphorylated thioureas of common formula RNHC(S)NHP(O)(OiPr)(2) (R = rBu, HL1:R = Ph, HLII; R = 4'-benzo- I 5-crown-5, HLIII) with Pd(PhCN)(2)Cl-2 in acetonitrile leads to complexes of the structure Pd(HL1-S)(2)Cl-2 (1), Pd(HLII-S)(2)Cl-2 (2) and Pd(HLIII-S)(2)Cl-2 (3). Reaction of N-phosphorylated thioureas of common formula RC(S)NHP(O)(OiPr)(2) (R = Et2N, HLIV; R = morpholine-N-yl, HLV) in the same conditions leads to complexes Pd(L-IV-O,S)(2) (4) and Pd(L-V-O,S)(2) (5), where the palladium(II) atoms are coordinated in a square-planar fashion by the C=S sulfur atoms and the P=O oxygen atoms of two anionic ligands. The crystal structure of complex I has been investigated by X-ray crystallography. It was established that the thiourea ligands are in a trans-configuration and the palladium(II) cation is coordinated by the sulfur atoms of the C=S groups and the chlorine atoms. Complex 1 is the first example of palladium(II) complex in which the potentially chelating N-phosphorylated thiourea ligand is bound through the sulfur atom only. (C) 2008 Elsevier Ltd. All rights reserved.