diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate | 425681-14-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate
• 英文别名: (E)-diethyl 4,8-dimethylnona-3,7-dienylphosphonate；diethyl 4,8-dimethyl-3,7-nonadienyl-1-phosphonate；homogeranyl diethyl phosphate；diethyl (E)-4,8-dimethylnona-3,7-dienylphosphonate；Diethyl P-[(3E)-4,8-dimethyl-3,7-nonadien-1-yl]phosphonate；(6E)-9-diethoxyphosphoryl-2,6-dimethylnona-2,6-diene
• CAS: 425681-14-7
• 化学式: C₁₅H₂₉O₃P
• 分子量: 288.367
• InChiKey: PVWKKGGOPYHALN-NTCAYCPXSA-N

物化性质

• 沸点：
  374.1±31.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate 在 咪唑 、 sodium hydride 、 magnesium 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (+)-(5S,10S)-13-acetoxypodocarpa-8,11,13-triene
  参考文献：
  名称：

  同型（聚异戊二烯基）芳烃的对映选择性仿生环化。(+)-Podpcarpa-8,11,13-三烯二萜和(-)-沉积源四环多戊二烯的新入口

  摘要：

  DOI：

  10.1021/ja003541x
• 作为产物：
  描述：

  香叶醇 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 diethyl ((E)-4,8-dimethyl-3,7-nonadienyl)phosphonate
  参考文献：
  名称：

  Synthesis of Prenyl Pyrophosphonates as New Potent Phosphoantigens Inducing Selective Activation of Human Vγ9Vδ2 T Lymphocytes

  摘要：

  gamma9delta2T cells represent the most abundant population of human blood gammadeltaT lymphocytes. They produce and promote strong cytotoxic activity against many pathogens that are implicated in several human infectious diseases. Their activation requires their exposure to small phosphorus-containing antigens in the family of prenyl pyrophosphates and their related biosynthetic precursors such as isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are naturally occurring metabolites in mycobacteria and several other microbial pathogens. The broad specificity in the recognition of these molecules by the T-lymphocyte population expressing a Vgamma9Vdelta2 cell receptor might facilitate their manipulation by designing small potent synthetic agonist ligands. In this paper, we describe the synthesis and the biological evaluation of new pyrophosphonate compounds as new isosteric analogues of natural prenyl pyrophosphates. Several prenyl and alkenyl pyrophosphonate with different chain lengths and degrees of insaturation (24-28, 48-50, and 64-66) were tested as well as the alkoxymethylpyrophosphonic analogue of IPP (compound 76) as its closest isostere. Several of them appeared to be better activators of Vgamma9Vdelta2 T cell proliferation than IPP. These results open the perspective of a potential use of isoprenoides pyrophosphonates as specific immunoregulatory molecules.

  DOI：

  10.1021/jm049861z

文献信息

• Phosphonates useful as modulators of t $g(g)9$g(d)2 lymphocyte activity
  申请人：Montero Jean-Louis

  公开号：US20060241087A1

  公开（公告）日：2006-10-26

  The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

  这项发明涉及新型膦酸酯衍生物，其制备方法，以及将其用作调节T γ9δ2淋巴细胞活性的配体和包含它们的药物组合物。
• Discovery of potent inhibitor for farnesyl pyrophosphate synthase in the mevalonate pathway
  作者：Jinbo Gao、Xiusheng Chu、Yongge Qiu、Long Wu、Yuqin Qiao、Jiasheng Wu、Ding Li

  DOI：10.1039/c0cc00992j

  日期：——

  The mevalonate pathway is an important drug target for the treatment of cancer and cardiovascular disease. We synthesized and studied a new type of nitrogen-containing bisphosphonate analogs and developed a sensitive end point assay method for enzyme FPPS, which was used for inhibitor screening. One potent FPPS inhibitor was discovered, and the structure-activity relationship of bisphosphonates for

  甲羟戊酸途径是治疗癌症和心血管疾病的重要药物靶标。我们合成并研究了一种新型的含氮双膦酸盐类似物，并开发了用于酶FPPS的灵敏的终点测定方法，该方法用于抑制剂筛选。发现了一种有效的FPPS抑制剂，并研究了双膦酸酯对酶失活的构效关系。
• Copper-mediated displacements of allylic THP ethers on a bisphosphonate template
  作者：Larry W. Shull、David F. Wiemer

  DOI：10.1016/j.jorganchem.2004.10.013

  日期：2005.5

  The copper-mediated displacement of allylic THP ethers by Grignard reagents has been examined in a system that contains a geminal bisphosphonate ester. With Grignard reagents derived from several aromatic halides or benzyl bromide the displacement proceeds in attractive yields, but more mixed results were obtained from reactions with alkyl halides. In addition to its role as a nucleophile, the Grignard

  已在包含双膦酸酯双键的系统中检查了格氏试剂在铜介导的烯丙基THP醚置换中的作用。使用衍生自几种芳族卤化物或苄基溴的格氏试剂，置换的产率很高，但与烷基卤的反应得到的混合结果更多。除了其作为亲核试剂的作用外，格氏试剂还似乎使双膦酸酯去质子化以生成阴离子中间体。这种阴离子的形成似乎限制了膦酸酯基团的竞争性亲核进攻，并提供了一种中间体，该中间体可以通过与亲电试剂（如甲基碘）反应而被捕获，以进入更取代的系统。
• Design and synthesis of non-hydrolyzable homoisoprenoid α-monofluorophosphonate inhibitors of PPAPDC family integral membrane lipid phosphatases
  作者：Thangaiah Subramanian、Hongmei Ren、Karunai Leela Subramanian、Manjula Sunkara、Fredrick O. Onono、Andrew J. Morris、H. Peter Spielmann

  DOI：10.1016/j.bmcl.2014.08.013

  日期：2014.9

  An efficient, diversity oriented synthesis of homoisoprenoid alpha-monofluorophosphonates utilizing electrophilic fluorination is presented along with their activity as inhibitors of PPAPDC2 family integral membrane lipid phosphatases. These novel phosphatase-resistant analogues of isoprenoid monophosphates are a platform for further structure-activity relationship studies and provide access to other isoprenoid family members where the phosphate ester oxygen is replaced by a alpha-monofluoromethylene moiety. (C) 2014 Elsevier Ltd. All rights reserved.
• US8017596B2
  申请人：——

  公开号：US8017596B2

  公开（公告）日：2011-09-13