cyclohexyl dihydrogen phosphate | 1623-22-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: cyclohexyl dihydrogen phosphate
• 英文别名: Cyclohexyl-dihydrogenphosphat；Cyclohexylphosphat；Phosphorsaeure-monocyclohexylester；cyclohexyl phosphate；Cyclohexanol phosphate
• CAS: 1623-22-9
• 化学式: C₆H₁₃O₄P
• 分子量: 180.141
• InChiKey: AKAUCGJQKLOHHK-UHFFFAOYSA-N

物化性质

• 沸点：
  329.2±25.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclohexyl dihydrogen phosphate 、 尿苷-5'-三磷酸 在 三正丁胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 Uridine-5''-cyclohexane-tetraphosphate
  参考文献：
  名称：

  Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists

  摘要：

  The phosphate, uracil, and ribose moieties of uracil nucleotides were varied structurally for evaluation of agonist activity at the human P2Y(2), P2Y(4), and P2Y(6) receptors. The 2-thio modi. cation, found previously to enhance P2Y2 receptor potency, could be combined with other favorable modi. cations to produce novel molecules that exhibit high potencies and receptor selectivities. Phosphonomethylene bridges introduced for stability in analogues of UDP, UTP, and uracil dinucleotides markedly reduced potency. Truncation of dinucleotide agonists of the P2Y(2) receptor, in the form of Up(4)-sugars, indicated that a terminal uracil ring is not essential for moderate potency at this receptor and that specific SAR patterns are observed at this distal end of the molecule. Key compounds reported in this study include 9, alpha, beta-methylene-UDP, a P2Y(6) receptor agonist; 30, Up(4)-phenyl ester and 34, Up(4)-[1] glucose, selective P2Y(2) receptor agonists; dihalomethylene phosphonate analogues 16 and 41, selective P2Y(2) receptor agonists; 43, the 2-thio analogue of INS37217 (P-1-(uridine-5')-P-4-(2'-deoxycytidine-5') tetraphosphate), a potent and selective P2Y(2) receptor agonist. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.05.013
• 作为产物：
  描述：

  环己醇 在 焦磷酸 作用下， 反应 1.0h， 生成 cyclohexyl dihydrogen phosphate
  参考文献：
  名称：

  焦磷酸磷酸化

  摘要：

  用焦磷酸通过非常简单的方法制备伯、仲脂肪醇和苯酚的磷酸二氢盐。通过对反应条件稍加修改，可以得到叔丁基和苄基磷酸二氢酯。出于磷酸化的目的，焦磷酸比正磷酸更具反应性。

  DOI：

  10.1246/bcsj.54.1891

文献信息

• Regioselective Phosphorylation of Carbohydrates and Various Alcohols by Bacterial Acid Phosphatases; Probing the Substrate Specificity of the Enzyme fromShigella flexneri
  作者：Teunie van Herk、Aloysius F. Hartog、Alida M. van der Burg、Ron Wever

  DOI：10.1002/adsc.200505072

  日期：2005.6

  broad range of carbohydrates and alcohols. Many cyclic carbohydrates are phosphorylated in a regioselective manner. Non-cyclic carbohydrates are phosphorylated as well. Phosphorylation of linear alcohols, cyclic and aromatic alcohols is also possible. In all cases the acid phosphatase from Shigella prefers a primary alcohol function above a secondary one. We conclude that these enzymes are an attractive

  细菌非特异性酸性磷酸酶通常催化多种底物的去磷酸化。如前所述，来自弗氏志贺氏菌和肠炎沙门氏菌的酶也能够使用廉价的焦磷酸盐作为磷酸盐供体，催化将肌苷磷酸化为肌苷单磷酸和将D-葡萄糖磷酸化为D-葡萄糖6-磷酸（D-G6P）。经过优化后，在后一反应中可实现高收率（95％），我们在此表明​​可以以制备方式使用这些酶。这促使我们使用31P NMR和HPLC还可以使多种碳水化合物和醇类进行磷酸化。许多环状碳水化合物以区域选择性方式被磷酸化。非环状碳水化合物也被磷酸化。直链醇，环状和芳族醇的磷酸化也是可能的。在所有情况下，志贺氏菌的酸性磷酸酶都比伯醇更喜欢伯醇功能。我们得出结论，在广泛范围的化合物磷酸化中，这些酶是现有化学和酶促方法的一种有吸引力的替代物。
• Mild and Chemoselective Phosphorylation of Alcohols Using a Ψ-Reagent
  作者：Michał Ociepa、Kyle W. Knouse、David He、Julien C. Vantourout、Dillon T. Flood、Natalia M. Padial、Jason S. Chen、Brittany B. Sanchez、Emily J. Sturgell、Bin Zheng、Shenjie Qiu、Michael A. Schmidt、Martin D. Eastgate、Phil S. Baran

  DOI：10.1021/acs.orglett.1c02736

  日期：2021.12.17

  An operationally simple, scalable, and chemoselective method for the direct phosphorylation of alcohols using a P(V)-approach based on the Ψ-reagent platform is disclosed. The method features a broad substrate scope of utility in both simple and complex settings and provides access to valuable phosphorylated alcohols that would be otherwise difficult to obtain.

  公开了一种操作简单、可扩展且化学选择性的方法，用于使用基于Ψ-试剂平台的P(V)-方法直接磷酸化醇。该方法的特点是在简单和复杂的环境中具有广泛的底物应用范围，并提供了获得有价值的磷酸化醇的途径，而这些是其他方法难以获得的。
• Human P2Y₁₄ Receptor Agonists: Truncation of the Hexose Moiety of Uridine-5′-Diphosphoglucose and Its Replacement with Alkyl and Aryl Groups
  作者：Arijit Das、Hyojin Ko、Lauren E. Burianek、Matthew O. Barrett、T. Kendall Harden、Kenneth A. Jacobson

  DOI：10.1021/jm901432g

  日期：2010.1.14

  Uridine-5′-diphosphoglucose (UDPG) activates the P2Y14 receptor, a neuroimmune system GPCR. P2Y14 receptor tolerates glucose substitution with small alkyl or aryl groups or its truncation to uridine 5′-diphosphate (UDP), a full agonist at the human P2Y14 receptor expressed in HEK-293 cells. 2-Thiouracil derivatives displayed selectivity for activation of the human P2Y14 vs the P2Y6 receptor, such as

  尿苷-5'-二磷酸葡萄糖 (UDPG) 激活 P2Y 14受体，这是一种神经免疫系统 GPCR。P2Y 14受体耐受用小烷基或芳基取代的葡萄糖或其截断为尿苷 5'-二磷酸 (UDP)，这是在 HEK-293 细胞中表达的人类 P2Y 14受体的完全激动剂。2-硫尿嘧啶衍生物显示出激活人 P2Y 14与 P2Y 6受体的选择性，例如 2-硫代-UDP 4（EC 50 = 1.92 nM，P2Y 14，选择性比 P2Y 6 高224 倍）及其β-丙氧基酯18 . 欧共体50UDP 的 β-甲基酯及其 2-硫代类似物的值分别为 2730 和 56 nM。β-叔的丁基酯4是11倍UDPG更有效，但β-芳氧基或更大，β支链烷基酯，例如环己基，不太有效。UDP 与刚性北或南甲氧基碳（双环 [3.1.0] 己烷） 组的核糖替代消除了 P2Y 14受体激动剂活性。α,β-亚甲基和二氟亚甲基对 P2Y 14
• Preparation of Phosphate and Pyrophosphate Esters by the Metal-catalyzed Reaction of 8-Quinolyl Phosphates
  作者：KINZO NAGASAWA、HISAE YOSHIDOME

  DOI：10.1248/cpb.21.2438

  日期：——

  In the presence of Cu (II) ion, alkyl 8-quinolyl hydrogen phosphates (alkyl=ethyl, cyclohexyl, and benzyl) converted into the corresponding P1, P2-disubstituted pyrophosphates with formation of 8-hydroxyquinoline-Cu (II) chelate in anhydrous pyridine. When this reaction was carried out in pyridine containing alcohols (R'=ethyl, amyl, cyclohexyl, and benzyl), corresponding dialkyl hydrogen phosphates (R-R'=ethyl-cyclohexyl, amyl-cyclohexyl, cyclohexyl-benzyl, and ethyl-benzyl) were formed as a sole product. The factors (water content, solvent, metal ion) which affect this metal-catalyzed reaction were examined, and a possible mechanism for the reaction was presented.

  在 Cu (II) 离子存在下，烷基 8-喹啉基氢磷酸酯（烷基=乙基、环己基和苄基）在无水吡啶中转化为相应的 P1、P2-二取代焦磷酸盐，并形成 8-羟基喹啉-Cu (II) 螯合物。当该反应在含有醇（R'=乙基、戊基、环己基和苄基）的吡啶中进行时，相应的二烷基氢磷酸盐（R-R'=乙基-环己基、戊基-环己基、环己基-苄基和乙基-苄基）作为唯一产物生成。研究了影响这种金属催化反应的因素（含水量、溶剂、金属离子），并提出了反应的可能机理。
• [EN] PROCESS FOR ISOLATING A (THIO)PHOSPHORIC ACID DERIVATIVE<br/>[FR] PROCÉDÉ POUR ISOLER UN DÉRIVÉ D'ACIDE (THIO)PHOSPHORIQUE
  申请人：BASF SE

  公开号：WO2017093925A1

  公开（公告）日：2017-06-08

  The present invention relates to a process for isolating at last one (thio)phosphoric acid derivative (1a), which has a boiling point of at least 70 °C, from a product mixture (1) comprising as component (1a) the at least one (thio)phosphoric acid derivative, as component (1b) at least one salt selected from (b1) ammonium salts and (b2) alkali metal chlorides, as component (1c) at least one polar solvent, which is selected from the group consisting of ester solvents and ether solvents, and optionally as component (1d) at least one HCl scavenger; wherein the process is based on the concept of first dissolving the (thio)phosphoric acid derivative (1a) to be able to remove the at least one salt, and then causing solids formation of the (thio)phosphoric acid derivative (1a).

  本发明涉及一种从包含至少一种（硫）磷酸衍生物（1a）的产品混合物（1）中分离至少一种（硫）磷酸衍生物（1a）的过程，其沸点至少为70°C，所述产品混合物（1）包括组分（1a）所述至少一种（硫）磷酸衍生物，组分（1b）至少一种选自（b1）铵盐和（b2）碱金属氯化物的盐，组分（1c）至少一种极性溶剂，所选自酯溶剂和醚溶剂的群体，以及可选地组分（1d）至少一种HCl清除剂；其中该过程基于首先溶解（1a）以能够去除至少一种盐，然后造成（1a）的固体形成的概念。