ethoxycarbonylphosphonic acid | 55920-71-3

• 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: ethoxycarbonylphosphonic acid
• 英文别名: (Ethoxycarbonyl)phosphonic acid
• CAS: 55920-71-3
• 化学式: C₃H₇O₅P
• mdl: MFCD11853132
• 分子量: 154.059
• InChiKey: WBIAZONFXLIADH-UHFFFAOYSA-N

物化性质

• 沸点：
  310.1±25.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethoxycarbonylphosphonic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到ethyl (dichlorophosphoryl)formate
  参考文献：
  名称：

  一种丙泊酚磷酰胺衍生物、其制备方法及其在医药上的用途

  摘要：

  一种丙泊酚磷酰胺衍生物、其制备方法及其在医药上的用途。本发明涉及一种通式(I)所示化合物及其立体异构体或药学上可接受的盐，以及医药中的应用，通式(I)化合物的结构如下所示，其基团定义与说明书定义一致。

  公开号：

  CN112390821A
• 作为产物：
  描述：

  bis(trimethylsilyl)(ethoxycarbonyl)phosphonate 在 水 作用下， 以 丙酮 为溶剂， 生成 ethoxycarbonylphosphonic acid
  参考文献：
  名称：

  溴代三甲基硅烷在膦酸酯脱烷基反应中的功能选择性

  摘要：

  溴代三甲基硅烷对混合的羧酸酯-膦酸酯烷基酯的P-O甲硅烷基脱烷基化反应具有高度选择性，可用于制备三甲基硅烷基酰胺基，炔基和碘代烷基膦酸酯，收率很高，因此使相应的膦酸易于通过中性H水解获得2 O.

  DOI：

  10.1039/c39790000739

文献信息

• Synthesis and antiviral activity of phosphonoacetic and phosphonoformic acid esters of 5-bromo-2'-deoxyuridine and related pyrimidine nucleosides and acyclonucleosides
  作者：Robert W. Lambert、Joseph A. Martin、Gareth J. Thomas、Ian B. Duncan、Michael J. Hall、Edgar P. Heimer

  DOI：10.1021/jm00122a014

  日期：1989.2

  Phosphonoacetic acid (PAA, 1) was coupled with various acyclonucleosides, 2'-deoxyuridines, cytidines, and arabinosyluracils, with 2,4,6-triisopropylbenzenesulfonyl chloride (TPS) or dicyclohexylcarbodiimide (DCCI) as condensing agents, to give a range of phosphonate esters. The carboxylic ester linkage of PAA to the 5'-position of 5-bromo-2'-deoxyuridine (BUdR, 3) was achieved via the mixed anhydride

  磷乙酸（PAA，1）与各种无环核苷，2'-脱氧尿苷，胞嘧啶核苷和阿拉伯糖基尿嘧啶偶合，并带有2,4,6-三异丙基苯磺酰氯（TPS）或二环己基碳二亚胺（DCCI）作为缩合剂，得到一系列膦酸酯酯。通过由（二乙基膦酰基）乙酸和三氟乙酸酐形成的混合酸酐，将PAA的羧酸酯键连接到5-溴-2'-脱氧尿苷（BUdR，3）的5'位置。通过使用DCCI方法将膦甲酸（PFA，2）与BUdR偶联，得到膦酸酯。在这些化合物中，只有2'-脱氧尿苷系列的膦酸酯对1型和2型单纯疱疹病毒显示出显着活性。BUdR-PAA衍生物和BUdR-PFA衍生物具有很高的活性，尤其是后者。它比亲本核苷BUdR对2型病毒更具活性。活性化合物可通过细胞外或细胞内水解作用作用于相应的抗病毒剂，但也可能涉及抗病毒活性的内在成分。
• 5′-Carbamoylphosphonyl-[6-3H]-AZT as a Tool for Studying Metabolic Transformations of the Nonradioactive Counterpart, an Inhibitor of HIV Replication
  作者：Dmitry V. Yanvarev、Elena A. Shirokova、Maria V. Astapova、Vyacheslav I. Shram、Marina K. Kukhanova、Yury S. Skoblov

  DOI：10.1080/15257770701505899

  日期：2007.11.26

  An effective synthesis of 5′-carbamoylphosphonyl-[6-3H]-AZT was developed from [6-3H]-AZT.For the synthesized compound, chemical and enzymatic stability were determined and its penetrationa cross HL-60 cell membranes was studied.

  以[6-3H]-AZT为原料开发了5′-氨基甲酰基膦酰基-[6-3H]-AZT的有效合成方法。对合成的化合物进行了化学稳定性和酶学稳定性测定，并研究了其对HL-60细胞膜的渗透性。
• Prodrugs of pharmaceuticals with improved bioavailability
  申请人：The Regents of the University of California

  公开号：US07517858B1

  公开（公告）日：2009-04-14

  Lipid prodrugs of pharmaceutical agents and their analogs that have increased anticancer, anti-viral, anti-inflammatory, anti-proliferative activity over the parent drug, and methods for making lipid prodrugs. Compositions comprising lipid prodrugs for treating disease and methods for treating disease which involve using the compositions.

  脂质类药物前体及其类似物，具有比原药物更强的抗癌、抗病毒、抗炎、抗增殖活性，并制备脂质类药物前体的方法。包含脂质类药物前体的组合物用于治疗疾病，以及使用该组合物治疗疾病的方法。
• 5′-Phosphonates of Ribonucleosides and 2′-Deoxyribonucleosides: Synthesis and Antiviral Activity
  作者：Maxim Jasko、Alexander Shipitsin、Elena Shirokova、Alexander Krayevsky、Bruce Polsky、Penny Baron、Clarinda MacLow、Michael Ostrander、Brian O'Hara

  DOI：10.1080/07328319308018558

  日期：1993.9

  5'-Phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-O-acylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonylphosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by action of ammonia in methanol or aqueous ammonia. 5'-Hydrogenphosphonothioates of thymidine and 3'-deoxythymidine were obtained by reaction of phosphinic acid in the presence of pivaloyl chloride with 3'-O-acetylthymidine or 3'-deoxythymidine, respectively, followed by addition of powedered sulfur. 5'-O-methylenephosphonates of thymidine and 2'-deoxyadenosine were prepared by intramolecular reaction of corresponding 3'-O-iodomethylphosphonates under basic conditions. All compounds were tested for inhibition of several viruses, including HSV-2 and CMV, but showed no activity. A few compounds insignificantly inhibited HIV-1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized anti-HIV action of 3'-azido-3'-deoxythymidine (AZT) and it indirectly showed that even some nucleoside 5'-phosphonates could be partly hydrolyzed in cell culture to corresponding nucleosides.
• PRODRUGS OF PHARMACEUTICALS WITH IMPROVED BIOAVAILABILITY
  申请人：HOSTETLER, Karl Y.

  公开号：EP0837630B1

  公开（公告）日：2007-12-26