Methylphosphonsaeure-cyclohexylester-chlorid | 7040-92-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Methylphosphonsaeure-cyclohexylester-chlorid
• 英文别名: [Chloro(methyl)phosphoryl]oxycyclohexane
• CAS: 7040-92-8
• 化学式: C₇H₁₄ClO₂P
• 分子量: 196.614
• InChiKey: NAFOPSBAMSOGMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  110 °C(Press: 5 Torr)
• 密度：
  1.1858 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methylphosphonsaeure-cyclohexylester-chlorid 在 氨 作用下， 以 乙醚 为溶剂， 反应 0.67h， 以31%的产率得到cyclohexyl methylphosphonamidate
  参考文献：
  名称：

  Synthesis of N?-phosphinatodiazene N-oxides

  摘要：

  We have developed a regiospecific method for synthesis of N'-phosphinatodiazene N-oxides, a previously unknown type of azoxy compounds in which the diazene oxide fragment is directly connected with the phosphinate group. The method involves reaction of amidoesters of alkyl- and arylphosphonic acids with nitroso compounds in the presence of dibromoisocyanurate.

  DOI：

  10.1007/bf00863379
• 作为产物：
  描述：

  甲基膦酞二氯 、 环己醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以63%的产率得到Methylphosphonsaeure-cyclohexylester-chlorid
  参考文献：
  名称：

  具有荧光离去基团的类似物，用于筛选和选择有效水解有机磷神经毒剂的酶。

  摘要：

  有效水解剧毒有机磷神经毒剂的酶可能被用作医疗对策。由于目前尚不清楚足够活跃的酶，我们合成了十二种具有 3-氯-7-氧基-4-甲基香豆素离去基团的有机磷神经毒剂荧光类似物作为高通量酶筛选的探针。这组包括杀虫剂对氧磷、对硫磷和二甲硫磷的类似物，以及神经毒剂 DFP、塔崩、沙林、环沙林、索曼、VX 和俄罗斯-VX。来自乙酰胆碱酯酶抑制的数据、代表性类似物（环沙林）的体内毒性试验以及来自 Pseudomonas diminuta 的磷酸三酯酶 (PTE) 和哺乳动物血清对氧磷酶 (PON1) 的动力学研究证实，这些类似物有效地模拟了亲本神经毒剂。

  DOI：

  10.1021/jm050518j

文献信息

• Hydrolyse Basique de phosphonates I. Étude qualitative
  作者：Henri Christol、Michel̀e Levy、Claude Marty

  DOI：10.1016/s0022-328x(00)88699-4

  日期：1968.6

  The hydrolysis of phosphonates by alkali in aqueous dioxane has been studied. The symmetrical phosphonates are hydrolysed with loss of one ester group to form a monoacid. With the mixed phosphonates the better leaving group is replaced.

  已经研究了在二恶烷水溶液中碱将膦酸酯水解的方法。对称的膦酸酯水解而失去一个酯基，形成一元酸。用混合的膦酸酯，更好的离去基团被取代。
• Solid-Phase Synthesis of Phosphonylated Peptides
  作者：Mary MacDonald、Marion Lanier、John Cashman

  DOI：10.1055/s-0030-1258132

  日期：2010.8

  syntheses of two series of phosphonylated peptides using Fmoc-protected amino acids. The peptides corresponded to regions containing phosphonylated Ser195 in the active site of butyrylcholinesterase and Tyr411 of human serum albumin. The phosphonylated Fmoc-protected amino acids were used in solid-phase peptide synthesis to prepare the peptides. Fmoc-serine and Fmoc-tyrosine with benzyl ester protection

  我们报告了使用 Fmoc 保护的氨基酸固相合成两个系列的膦酰化肽。这些肽对应于丁酰胆碱酯酶活性位点中含有磷酸化 Ser195 和人血清白蛋白 Tyr411 的区域。磷酸化 Fmoc 保护的氨基酸用于固相肽合成以制备肽。具有苄酯保护的 Fmoc-丝氨酸和 Fmoc-酪氨酸用烷基甲基膦酸一氯化物处理以膦酰化侧链羟基。膦酰化肽被设计为模拟蛋白质暴露于有机磷试剂后的蛋白质区域。
• Chemical and biochemical adducts as biomarkers for organophosphate exposure
  申请人：Human BioMolucular Research Institute

  公开号：US10711037B2

  公开（公告）日：2020-07-14

  Provided are methods for identifying OP-adducted biomarkers of OP exposure as well as compounds containing OPs that can provide OP adducts and compounds of Formula 1 for eliciting antibodies that specifically and selectively bind to the OP adducts, wherein the Formula 1 compounds have the structure of OP-Peptide-Linker-CP, wherein CP is a carrier protein, OP represents a structure corresponding to that of a reactive organic phosphorous compound covalently modifying a tyrosine residue hydroxyl group of the peptide of Formula I and the other variable groups are as described herein.

  本发明提供了用于鉴定 OP 暴露的 OP 加合物生物标志物的方法以及含有 OP 的化合物，这些化合物可提供 OP 加合物和用于激发特异性和选择性结合 OP 加合物的抗体的式 1 化合物，其中式 1 化合物具有 OP-Peptide-Linker-CP 结构，其中 CP 是载体蛋白，OP 代表与共价修饰式 I 肽的酪氨酸残基羟基的活性有机磷化合物结构相对应的结构，其他可变基团如本文所述。
• Phosphylated tyrosine in albumin as a biomarker of exposure to organophosphorus nerve agents
  作者：Nichola H. Williams、John M. Harrison、Robert W. Read、Robin M. Black

  DOI：10.1007/s00204-007-0191-8

  日期：2007.8.3

  cyclosarin and tabun phosphylate a tyrosine residue on albumin in human blood. These adducts may offer relatively long-lived biological markers of nerve agent exposure that do not 'age' rapidly, and which are not degraded by therapy with oximes. Sensitive methods for the detection of these adducts have been developed using liquid chromatography-tandem mass spectrometry. Adducts of all four nerve agents were detected in the blood of exposed guinea pigs being used in studies to improve medical countermeasures. The tyrosine adducts with soman and tabun were detected in guinea pigs receiving therapy 7 days following subcutaneous administration of five times the LD50 dose of the respective nerve agent. VX also forms a tyrosine adduct in human blood in vitro but only at high concentrations.
• Phosphorylation of Tyrosine and Tyr-Thr-Lys Tripeptide with Cyclohexylmethyl- and (Deuteromethyl)phosphonochloridates
  作者：I. A. Rodin、T. M. Baygildiev、V. I. Krylov、V. N. Osipov、I. I. Krylov、V. A. Yashkir、I. V. Rybalchenko

  DOI：10.1134/s1070363220040106

  日期：2020.4

  Methods for phosphorylation of tyrosine and Tyr-Thr-Lys tripeptide with cyclohexylmethyl(deuteromethyl)phosphonochloridates have been developed. These products can be used as reference compounds in the analysis of blood plasma of patients presumably exposed to cyclohexylmethylphosphonofluoridate (cyclosarin) action. Conditions for the separation and purification of the synthesized intermediates by means of chromatography have been determined and optimized, allowing high-purity phosphorylated products at the final stage of the synthesis.