diethyl ω-azidopentylphosphonate | 174537-99-6

• 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: diethyl ω-azidopentylphosphonate
• 英文别名: diethyl (5-azidopentyl)phosphonate；1-azido-5-diethoxyphosphorylpentane
• CAS: 174537-99-6
• 化学式: C₉H₂₀N₃O₃P
• 分子量: 249.25
• InChiKey: LNNYRWXBDBBPFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl ω-azidopentylphosphonate 在 氢氧化钾 、 sodium hydroxide 、 三甲基溴硅烷 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.08h， 生成 [5-(5-Amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-pentyl]-phosphonic acid
  参考文献：
  名称：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]嘧啶（8-氮杂鸟嘌呤）膦酸酯无环衍生物是嘌呤核苷磷酸化酶的抑制剂。

  摘要：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]-嘧啶（8-氮杂鸟嘌呤）的膦酸酯无环衍生物是嘌呤核苷磷酸化酶（PNPase）的抑制剂，其Ki'值范围为0.05至1.6 microM。这些化合物是有效的PNPase抑制剂无环鸟苷二磷酸的酶稳定同类物（53）。

  DOI：

  10.1021/jm950736k
• 作为产物：
  描述：

  5-hydroxypentylphosphonic acid diethyl ester 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 diethyl ω-azidopentylphosphonate
  参考文献：
  名称：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]嘧啶（8-氮杂鸟嘌呤）膦酸酯无环衍生物是嘌呤核苷磷酸化酶的抑制剂。

  摘要：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]-嘧啶（8-氮杂鸟嘌呤）的膦酸酯无环衍生物是嘌呤核苷磷酸化酶（PNPase）的抑制剂，其Ki'值范围为0.05至1.6 microM。这些化合物是有效的PNPase抑制剂无环鸟苷二磷酸的酶稳定同类物（53）。

  DOI：

  10.1021/jm950736k

文献信息

• Novel phosphonate analogs of sulforaphane: Synthesis, in vitro and in vivo anticancer activity
  作者：Mateusz Psurski、Łukasz Janczewski、Marta Świtalska、Anna Gajda、Tomasz M. Goszczyński、Józef Oleksyszyn、Joanna Wietrzyk、Tadeusz Gajda

  DOI：10.1016/j.ejmech.2017.03.028

  日期：2017.5

  of over forty, novel, structurally diverse phosphonate analogs of sulforaphane (P-ITCs) were designed, synthesized and fully characterized. All compounds were evaluated for antiproliferative activity in vitro on Lovo and LoVo/DX colon cancer cell lines. All compounds exhibited high antiproliferative activity, comparable or higher to the activity of naturally occurring benzyl isothiocyanate and sulforaphane

  设计，合成和充分表征了四十多种新颖，结构多样的萝卜硫烷膦酸酯类似物（P-ITC）的文库。评价了所有化合物在体外对Lovo和LoVo / DX结肠癌细胞系的抗增殖活性。所有化合物均显示出高抗增殖活性，与天然存在的异硫氰酸苄酯和萝卜硫烷相当或更高。对所选化合物的作用机理的评估显示了它们作为G2 / M细胞周期停滞和凋亡诱导剂的潜力。使用一组选自结肠，肺，乳腺和子宫以及正常鼠成纤维细胞的选定细胞系，对选定化合物进行了进一步的抗增殖研究。与异硫氰酸苄酯相比，对萝卜硫烷的膦酸酯类似物的体内研究显示出较低的活性。我们的研究表明，新合成的P-ITC可以用作合成具有更高抗癌活性的新型异硫氰酸酯的起点。
• A novel click-chemistry approach to flame retardant polyurethanes
  作者：Ana M. Borreguero、Pallavi Sharma、Christian Spiteri、María M. Velencoso、Manuel S. Carmona、John E. Moses、Juan F. Rodríguez

  DOI：10.1016/j.reactfunctpolym.2013.06.003

  日期：2013.9

  The low thermo-oxidative properties of PU foams somewhat limits their practical application, particularly as heat sensitive materials. The introduction of a covalently linked flame retardant organophosphonate ester into the PU foam was achieved using the CuAAC 'click' reaction of an alkyne-polyol and azidoalkylmonophosphonate. These functionalised materials were prepared in four steps: first, a number of azidoalkyl monophosphonate compounds were formed via nucleophilic substitution of bromoalkylphosphonates with NaN3; next, polyols bearing terminal alkyne groups were prepared by anionic ring opening copolymerization between propylene oxide and glycidyl propargyl ether; followed by 'clicking' the azidoalkylphosphonate to the polyol and finally, synthesis of the PU foam with 2.4 wt% of "click-polyol". The functionalised PU foam demonstrated a well-formed polyhedral cell structure and an increase in the fire resistance, according to the SEM and thermogravimetric analysis, respectively. Even after thermal treatment at 400 degrees C, the new PU foam material displayed enhanced flame resistant properties by forming a char layer on the surface of the polymer, whilst maintaining its polyhedral structure. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of triazolyl-alkylphosphonate starting from ω-azidoalkylphosphonates or ω-alkynylphosphonates
  作者：Lise Delain-Bioton、Didier Villemin、Jean-François Lohier、Jana Sopkova、Paul-Alain Jaffrès

  DOI：10.1016/j.tet.2007.07.024

  日期：2007.9

  1,2,3-Triazolyl-alkylphosphonates are synthesised according to a Huisgen 1,3-dipolar cycloaddition catalysed by copper salts. The cycloaddition of either an alkynylphosphonate with an azidoalkane or an azido-phosphonate with an alkyne is achieved in high yield and regiospecifically. As an illustration of the functionalisation of aromatic ligands by using the catalytic version of the Huisgen reaction, the coupling of 3-ethynyl-1,10-phenanthroline with azidoalkylphosphonate is reported. (c) 2007 Elsevier Ltd. All rights reserved.