diethyl (2-oxodecyl)phosphonate | 131721-21-6

• 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 (2-oxodecyl)phosphonate
• 英文别名: 1-diethoxyphosphoryldecan-2-one
• CAS: 131721-21-6
• 化学式: C₁₄H₂₉O₄P
• 分子量: 292.356
• InChiKey: FIAPXLGOCRSZGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (2-oxodecyl)phosphonate 、 (2S)-6-乙氧基-1,6-二氧代-2-己烷基苯甲酸酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到[(E,5S)-1-ethoxy-1,8-dioxohexadec-6-en-5-yl] benzoate
  参考文献：
  名称：

  β-cetophosphonates: Precurseurs d'analogues du LTB4.

  摘要：

  DOI：

  10.1016/s0040-4039(00)97561-0
• 作为产物：
  描述：

  Dec-1-inylphosphonsaeure-diethylester 在 2-二环己基膦-2′,4′,6′-三异丙基联苯金(I) 双(三氟甲烷磺酰)亚胺 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以94%的产率得到diethyl (2-oxodecyl)phosphonate
  参考文献：
  名称：

  金(I)-催化的炔基膦酸盐水合：有效获取β-酮膦酸盐

  摘要：

  已成功开发了一种通用、高效且高度区域选择性的方案，该方案使用金 (I) 络合物催化系统将炔基膦酸酯转化为相应的 β-酮膦酸酯。该方法可生产多种β-酮膦酸酯，具有反应条件温和、官能团耐受性高、收率高等优点。

  DOI：

  10.1002/ejoc.201400066

文献信息

• Synthesis of structural analogs of leukotriene B4 and their receptor binding activity
  作者：William D. Kingsbury、Israil Pendrak、Jack D. Leber、Jeffery C. Boehm、Brenda Mallet、Henry M. Sarau、James J. Foley、Dulcie B. Schmidt、Robert A. Daines

  DOI：10.1021/jm00074a012

  日期：1993.10

  DMSO differentiated U-937 cells. The first analog prepared, quinoline 3, displayed moderate potency in the LTB4 receptor binding assay (Ki = 0.9 microM). Modification of 3 by appending an aromatic ring between carbons 2 and 4 of the acid side chain produced a dramatic increase in receptor binding (15, Ki = 0.01 microM); a further improvement in receptor binding was achieved in the pyridine series (e.g

  白三烯B4（LTB4）的结构类似物是使用LTB4的优选构象设计的（1）。在LTB4碳7和11之间加一个芳香环骨架可导致喹啉类似物3和15。对碳7和9之间的LTB4结构的类似修饰可导致吡啶类似物41和46。在受体结合中评估了该研究的化合物[3H] LTB4和完整的人DMSO分化的U-937细胞进行检测。制备的第一个类似物喹啉3在LTB4受体结合试验中显示中等效力（Ki = 0.9 microM）。通过在酸侧链的碳2和碳4之间附加一个芳环对3进行修饰，可以使受体结合显着增加（15，Ki = 0.01 microM）。在吡啶系列中实现了受体结合的进一步改善（例如41； Ki ＝0.001μM）。使用依赖于LTB4诱导的细胞内钙动员的功能测定来确定测试化合物的LTB4受体激动剂/拮抗剂活性。在本报告中制备的类似物中，只有47个表现出LTB4受体拮抗剂活性。
• Gold(I)-Catalyzed Hydration of Alkynylphosphonates: Efficient Access to β-Ketophosphonates
  作者：Longyong Xie、Rui Yuan、Ruijia Wang、Zhihong Peng、Jiannan Xiang、Weimin He

  DOI：10.1002/ejoc.201400066

  日期：2014.5

  A general, efficient, and highly regioselective protocol with the use of a gold(I) complex catalytic system for the transformation of alkynylphosphonates into the corresponding β-ketophosphonates has been successfully developed. This method produces a variety of β-ketophosphonates with the advantages of mild reaction conditions, high functional-group tolerance, and excellent yields.

  已成功开发了一种通用、高效且高度区域选择性的方案，该方案使用金 (I) 络合物催化系统将炔基膦酸酯转化为相应的 β-酮膦酸酯。该方法可生产多种β-酮膦酸酯，具有反应条件温和、官能团耐受性高、收率高等优点。
• Synthesis and Structure−Activity Relationships of New 1,3-Disubstituted Cyclohexanes as Structurally Rigid Leukotriene B₄ Receptor Antagonists
  作者：Jean-Marc Poudrel、Pierre Hullot、Jean-Pierre Vidal、Jean-Pierre Girard、Jean-Claude Rossi、Agnès Muller、Claude Bonne、Vladimir Bezuglov、Igor Serkov、Pierre Renard、Bruno Pfeiffer

  DOI：10.1021/jm9910573

  日期：1999.12.1

  A series of 1-hydroxy-3-[3-hydroxy-7-phenyl-1-hepten-1-yl] cyclohexane acetic acid derivatives was designed based on postulated active conformation of leukotriene B-4 (LTB4) and evaluated as human cell surface LTB4 receptor (BLTR) antagonists. Binding was determined through [H-3]LTB4 displacement from human neutrophils and receptor antagonistic assays by in vitro measurements of inhibition of leukocyte chemotaxis induced by LTB4. On the basis of these assays, a structure-affinity relationship was investigated. Optimization of the acid chain length and omega-substitution of a phenyl group on the lipophilic tail were shown to be critical for binding activity. These modifications led to the discovery of compounds with submicromolar potency and selective BLTR antagonism. The most potent compound 3b alpha (IC50 = 250 nM) was found to significantly inhibit oedema formation in a topical model of phorbolester-induced inflammation. Substantial improvement of in vitro potency was achieved by modification of the carboxylic acid function leading to the identification of the N,N-dimethylamide series. Compound 5b alpha, free of agonist activity, displayed higher potency in receptor binding with an IC50 of 40 nM. These results support the hypothesis that the spatial relationship between the carboxylic acid and allylic hydroxyl functions is crucial for high binding affinity with BLTR.
• DURAND, THIERRY;SAVIGNAC, PH.;GIRARD, JEAN-PIERRE;ESCALE, ROGER;ROSSI, JE+, TETRAHEDRON LETT., 31,(1990) N9, C. 4131-4134
  作者：DURAND, THIERRY、SAVIGNAC, PH.、GIRARD, JEAN-PIERRE、ESCALE, ROGER、ROSSI, JE+

  DOI：——

  日期：——
• Synthesis of β-ketophosphonates via AgNO3-catalyzed hydration of alkynylphosphonates: a rate-enhancement effect of methanol
  作者：Jiannan Xiang、Niannian Yi、Ruijia Wang、Linghui Lu、Huaxu Zou、Yuan Pan、Weimin He

  DOI：10.1016/j.tet.2014.12.001

  日期：2015.1

  beta-Ketophosphonates were prepared via AgNO3-catalyzed hydration of alkynylphosphonates with a dramatic rate-enhancement effect of methanol. This benign aqueous-methanol method catalyzed by a low-(c)ost catalyst has simple, atom-economical procedure, and was used effectively with a wide range of substrates. (C) 2014 Elsevier Ltd. All rights reserved.