ethyl hydrogen 5-hexenylphosphonate | 141917-77-3

• 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: ethyl hydrogen 5-hexenylphosphonate
• 英文别名: ethyl hydrogen hex-5-en-1-ylphosphonate；Ethoxy(hex-5-enyl)phosphinic acid
• CAS: 141917-77-3
• 化学式: C₈H₁₇O₃P
• 分子量: 192.195
• InChiKey: LAYVLNHZWMFJOT-UHFFFAOYSA-N

物化性质

• 沸点：
  283.5±33.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl hydrogen 5-hexenylphosphonate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以100%的产率得到ethyl (5-hexenylphosphono)chloridate
  参考文献：
  名称：

  [[(Guaninylalkyl)phosphinico]methyl]phosphonic Acids. Multisubstrate Analog Inhibitors of Human Erythrocyte Purine Nucleoside Phosphorylase

  摘要：

  A series of [[(guaninylalkyl)phosphinico]methyl]phosphonic acids, 2, was synthesized and tested as inhibitors of human erythrocyte purine nucleoside phosphorylase (PNPase). The target (phosphinicomethyl)phosphonic acids 2 were synthesized in six or seven steps from alkenylphosphonates 4. The latter were converted to the intermediate alkylmesylates 9 in a series of steps that included (1) conversion of the diethyl phosphonates 4 to the (phosphinoylmethyl)pho sphonates 7 and (2) conversion of the terminal double bond of [(alkenylphosphinoyl)methyl]-phosphonates 7 to the alkylmesylates 9. The pure 9-isomers 2 were obtained by alkylation of 2-amino-6-(2-methoxyethoxy)-9H-purine with alkylmesylates 9 followed by hydrolysis of the protecting groups with concentrated hydrochloric acid and ion exchange chromatography to give 2 as hydrated ammonium salts. The most potent inhibitor of human erythrocyte PNPase, [[[5-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)pentyl]phosphinico]methyl]phosphonic acid(2b), was a multisubstrate analogue inhibitor with a K-i' of 3.1 nM. Optimum PNPase inhibitory activity required the presence of zinc ions in the assay medium. These potent inhibitors of PNPase exhibited only weak activity against human leukemic T-cells in vitro.

  DOI：

  10.1021/jm00006a020
• 作为产物：
  描述：

  6-碘-1-己烯 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl hydrogen 5-hexenylphosphonate
  参考文献：
  名称：

  通过无环二烯复分解的链内聚膦酸酯

  摘要：

  通过三种不同单体的无环二烯复分解聚合反应制备了链内聚膦酸酯。已经开发出具有不对称结构的新型不饱和膦酸酯单体。单体可通过三步合成法轻松获得，可轻松按比例放大。这是关于烯烃复分解的聚（膦酸酯）的首次报道，其中稳定的碳-磷键位于聚合物主链中。与其他聚磷酸酯相比，这改变了降解产物的性质。分子量高达31000 g mol –1的聚合物可以实现并已详细描述了NMR光谱，尺寸排阻色谱，热重分析和差示扫描量热法。就结晶（SAXS，WAXS）及其流变行为而言，它们也已与结构类似物多磷酸盐进行了比较。而且，分析了溶液生长的晶体，使得本文报道的一些聚膦酸酯成为有趣的缺陷类聚（乙烯）样结构。

  DOI：

  10.1021/acs.macromol.6b00366

文献信息

• Selective hydrolysis of phosphorus(<scp>v</scp>) compounds to form organophosphorus monoacids
  作者：Jeffrey Ash、Hai Huang、Paula Cordero、Jun Yong Kang

  DOI：10.1039/d1ob00881a

  日期：——

  phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(V)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

  已经开发了一种用于合成难以捉摸的膦酸、次膦酸和磷酸单酸的无叠氮化物和过渡金属的方法。惰性五价 P( V )-化合物（膦酸盐、次膦酸盐和磷酸盐）被三氟甲磺酸酐 (Tf 2 O)/吡啶体系活化，形成高反应性磷酰吡啶鎓中间体，该中间体经过 H 2 O 的亲核取代以选择性脱保护一个烷氧基基团形成有机磷单酸。
• Heterocyclic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0478292A1

  公开（公告）日：1992-04-01

  Compounds of the formula (I): or a pharmaceutically acceptable salt or ester thereof, wherein X¹, is nitrogen or a group CH and X² is nitrogen or a group CR⁵ wherein R⁵ is hydrogen, hydroxy, halo or a group NHR⁶ wherein R⁶ is hydrogen or a C₁₋₄ alkyl or C₁₋₄ alkylcarbonyl group, R¹ is amino or hydrogen; R² is hydrogen, halo, SH, a group NHR⁷ wherein R⁷ is hydrogen or a C₁₋₄ alkyl or C₁₋₄ alkylcarbonyl group or R² is a group OR⁸ wherein R⁸ is hydrogen, C₁₋₄ alkyl or benzyl, R³ and R⁴ are the same or different and each is hydrogen or halo, X³ is a chain containing m CH₂ groups and n oxygen atoms, m being 1, 2, 3, 4, or 5 and n being 0, 1 or 2 the sum of m and n being 2, 3, 4, 5, or 6; are disclosed as inhibitors of the enzyme, purine nucleoside phosphorylase, pharmaceutical compositions containing the compounds, their use in medicine and processes for their preparation are also described.

  式(I)的化合物或其医药上可接受的盐或酯，其中X¹为氮或CH基团，X²为氮或CR⁵基团，其中R⁵为氢、羟基、卤素或NHR⁶基团，其中R⁶为氢或C₁₋₄烷基或C₁₋₄烷基羰基基团，R¹为氨基或氢；R²为氢、卤素、SH、NHR⁷基团，其中R⁷为氢或C₁₋₄烷基或C₁₋₄烷基羰基基团，或R²为OR⁸基团，其中R⁸为氢、C₁₋₄烷基或苄基，R³和R⁴相同或不同，均为氢或卤素，X³为含有m个CH₂基团和n个氧原子的链，其中m为1、2、3、4或5，n为0、1或2，m和n的总和为2、3、4、5或6；作为嘌呤核苷酸磷酸化酶的抑制剂进行了披露，还描述了含有该化合物的制药组合物、它们在医学上的用途以及其制备方法。