2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς³λ³-phosphorin-4,6-dione | 77507-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 英文名称: 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς³λ³-phosphorin-4,6-dione
• 英文别名: 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2σ³λ³-phosphorin-4,6-dione；1,3,5-Trimethyl-2-chlor-1,3,5-triaza-2-ς³λ³-phosphorin-4,6-dion；2-Chloro-1,3,5-trimethyl-1,3,5,2-triazaphosphinane-4,6-dione
• CAS: 77507-71-2
• 化学式: C₅H₉ClN₃O₂P
• 分子量: 209.572
• InChiKey: SEQGRAXERPPDRT-UHFFFAOYSA-N

物化性质

• 沸点：
  231.1±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς³λ³-phosphorin-4,6-dione 在 碘代三甲硅烷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以89%的产率得到2-iodo-1,3,5-trimethyl-4,6-dioxo-1,3,5,2λ3-triazaphosphinane
  参考文献：
  名称：

  Meyer, Thomas G.; Jones, Peter G.; Schmutzler, Reinhard, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 4, p. 517 - 525

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-二甲基-1-(甲基氨基甲酰基)脲 在 三氯化磷 作用下， 以 甲苯 为溶剂， 反应 120.0h， 以90%的产率得到2-chloro-1,3,5-trimethyl-1,3,5-triaza-2ς³λ³-phosphorin-4,6-dione
  参考文献：
  名称：

  Meyer, Thomas G.; Jones, Peter G.; Schmutzler, Reinhard, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 4, p. 517 - 525

  摘要：

  DOI：

文献信息

• A New Method for the Preparation of Ifosfamide and Cyclophosphamide
  作者：I Neda、R Sonnenburg、R Schmutzler、U Niemeyer、B Kutscher、J Engel、A Kleemann

  DOI：10.1515/znb-1997-0810

  日期：1997.8.1

  The reaction of 2-chloro-3-(2-chloroethyl)-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide 1 and 2-chloro-tetrahydro-2H-1,3,2-oxazaphosphorin-2-oxide 2 with 2-(trimethylsilyloxy)ethylamine 3 and bis-[2-(trimethylsiloxy)ethyl]amine 4, respectively, yielded the trimethylsilylated compounds 5 and 6, analogous to ifosfamide and cyclophosphamide. The reaction of 5 and 6 with 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2-phosphorin-4,6-dione 7 led to the diphosphorus compounds 8 and 9 which could be transformed to ifosfamide 11 and cyclophosphamide 12 by treatment with sulfuryl chloride. This synthesis shows that the alkylating agents 2- chloroethylammonium chloride and bis-(2-chloroethyl)ammonium chloride can be avoided and the chlorine atom can be introduced in the final reaction step of the synthesis of 11 and 12.

  2-氯-3-(2-氯乙基)-四氢-2H-1,3,2-氧杂磷杂环戊烷-2-氧化物1和2-氯-四氢-2H-1,3,2-氧杂磷杂环戊烷-2-氧化物2与2-(三甲基硅氧基)乙胺3和双-[2-(三甲基硅氧基)乙基]胺4分别反应，得到类似于异环磷酰胺和环磷酰胺的三甲基硅基化合物5和6。5和6与2-氯-1,3,5-三甲基-1,3,5-三氮杂-2-磷杂环己烷-4,6-二酮7反应，生成二磷化合物8和9，可以通过与亚硫酰氯处理转化为异环磷酰胺11和环磷酰胺12。这种合成表明，可以避免烷基化剂2-氯乙基铵盐和双-(2-氯乙基)铵盐，并且氯原子可以在合成11和12的最终反应步骤中引入。
• Synthesis of new calix[4]arene-based phosphorus ligands and their application in the Rh(I) catalyzed hydroformylation of 1-octene
  作者：C. Kunze、D. Selent、I. Neda、R. Schmutzler、A. Spannenberg、A. Börner

  DOI：10.1002/hc.1088

  日期：——

  The synthesis of calix[4]arene-based phosphorus diamides and phosphites is described. These oligocyclic ligands have been tested in the Rh(I)- catalyzed hydroformylation of 1-octene. Depending on the reaction conditions, yields up to 99% and n/iso-selectivities between 0.7 and 2.6 have been observed. tert-Butyl groups on the upper rim of the calix[4]arene template had a beneficial effect on the catalytic

  描述了基于杯[4]芳烃的磷二酰胺和亚磷酸酯的合成。这些寡环配体已在 Rh(I) 催化的 1-辛烯加氢甲酰化中进行了测试。根据反应条件，观察到产率高达 99%，n/iso 选择性介于 0.7 和 2.6 之间。杯[4]芳烃模板上缘的叔丁基对催化反应具有有益作用。一般来说，双缩脲衍生的 P 配体是优越的。为了比较，还合成了相应的“单体”配体并用于催化反应。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:577–585, 2001
• Ethoxy-tethered calix[4]arenes containing P(III) substituents and trimethylsiloxy groups as building blocks in supramolecular chemistry; cis/trans intra- and intermolecular complexation of dichloroplatinum(II) fragments
  作者：Ion NEDA、Ionel BALCU、Corina MACARIE

  DOI：10.33224/rrch.2021.66.2.05

  日期：——

  p-tert-Butylcalix[4]arene 1 reacts with bromoethyl acetate and LiAlH4 to form the p-tert-butyl-tetrakis(2-hydroxyethoxy)calix[4]arene 8 bearing four ethyl-spacers at the lower rim of the calixarene. Reaction of 8 with Et2NSiMe3 leads to the tetrakis-substituted derivative 9. Treatment of 9 with PF2Cl gives the stable tetrakis-fluorophosphite 10, while the reaction with 2-chloro-1,3,5-trimethyl-1,3,5-triaza-2σ3λ3-phosphorin-4,6-dione furnishes the tetrakis-substituted molecule 11. When 11 was allowed to react with SO2Cl2, formation of the tetrakis(2-chloro)ethyl substituted calix[4]arene 13 was observed. All examined calixarene derivatives are exclusively obtained in the cone conformer. Reaction of 11 with dichloro(cyclooctadiene)platinum(II) leads to the symmetrically four-times bridged dimmer 15, which exhibits a trans orientation of the atoms surrounding the platinum(II) atom and involves all eight phosphorus atoms in the bridges. When 10 was treated with (COD)PtCl2, the cis intermolecular complex 16 was obtained.

  p-叔丁基杯[4]芳烃1与溴乙酸乙酯和LiAlH4反应，形成带有四个乙基间隔的p-叔丁基四(2-羟乙氧基)杯[4]芳烃8，位于杯芳烃的下缘。将8与Et2NSiMe3反应可得到四取代衍生物9。将9与PF2Cl处理可得到稳定的四取代氟代膦酸酯10，而与2-氯-1,3,5-三甲基-1,3,5-三氮杂-2σ3λ3-磷杂环戊二烯-4,6-二酮反应可得到四取代分子11。当11与SO2Cl2反应时，观察到四取代(2-氯乙基)取代的杯[4]芳烃13的形成。所有检查过的杯芳烃衍生物均仅以锥形构象获得。将11与二氯(环辛二烯)铂(II)反应可得到对称四次桥接的二聚体15，其展示了围绕铂(II)原子的原子的反式定向，并涉及桥接中的所有八个磷原子。当10与(COD)PtCl2处理时，可得到顺式分子间配合物16。
• Synthese und Komplexierung Phosphorylierter spacer-modifizierter Glucosederivate/ Synthesis and Complexation of Spacer Modified Phosphorylated Glucose Derivatives
  作者：Tjark Siedentop、Ion Neda、Reinhard Schmutzler

  DOI：10.1515/znb-2000-1011

  日期：2000.10.1

  Treatment of the spacer modified glucose derivative 1 with diethylaminotrimethylsilane furnished the bis-silylated molecule 2. Reaction of 2 with two equivalents of the phosphorus compounds 3, 4, and 5 led to the spacer phosphorylated glucosyl derivatives 6, 7 and 8. Complexation of 6 with (COD)PtCl₂ gave complex 9; the cis-conformation of 9 could be confirmed by ³¹P NMR investigations

  将经过空间修饰的葡萄糖衍生物1与二乙氨基三甲基硅烷反应，得到双硅烷化分子2。将2与磷化合物3、4和5的两当量反应，得到空间磷酸化葡萄糖衍生物6、7和8。将6与(COD)PtCl₂络合，得到络合物9；通过³¹P NMR研究，确认9的顺式构象。

• Neda, Ion; Farkens, Michael; Schmutzler, Reinhard, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1994, vol. 49, # 2, p. 165 - 170
  作者：Neda, Ion、Farkens, Michael、Schmutzler, Reinhard

  DOI：——

  日期：——