甲基6-(二甲氧基磷酰)-5-氧代己酸酯 | 104227-38-5

• 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
• 中文名称: 甲基6-(二甲氧基磷酰)-5-氧代己酸酯
• 英文名称: methyl 6-(dimethoxyphosphoryl)-5-oxohexanoate
• 英文别名: 2-Oxo-5-carbomethoxypentan-dimethylphosphonat；Methyl 6-dimethoxyphosphoryl-5-oxo-hexanoate；methyl 6-dimethoxyphosphoryl-5-oxohexanoate
• CAS: 104227-38-5
• 化学式: C₉H₁₇O₆P
• 分子量: 252.204
• InChiKey: PMOYKTGCMQTQNB-UHFFFAOYSA-N

物化性质

• 沸点：
  346.7±22.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2920909090

反应信息

• 作为反应物：
  描述：

  甲基6-(二甲氧基磷酰)-5-氧代己酸酯 在 sodium hexamethyldisilazane 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 6.25h， 生成 (E)-7-(naphthalen-1-yl)-5-oxohept-6-enoic acid
  参考文献：
  名称：

  5-Oxo-ETE Receptor Antagonists

  摘要：

  5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.

  DOI：

  10.1021/jm400480j
• 作为产物：
  描述：

  戊二酸单甲酯 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 甲基6-(二甲氧基磷酰)-5-氧代己酸酯
  参考文献：
  名称：

  Chemoselective Synthesis of β-Ketophosphonates Using Lithiated α-(Trimethylsilyl)methylphosphonate

  摘要：

  A highly chemoselective synthesis of beta-ketophosphonates from pentafluorophenyl esters and lithiated methyl alpha-(trimethylsilyl)methylphosphonate has been developed. This mild lithiated phosphonate reagent allows the synthesis of functionalized beta-ketophosphonates in the presence of unactivated esters with high yields. This method has been compared with the standard lithiated methylphosphonate reagent.

  DOI：

  10.1021/acs.joc.5b00039

文献信息

• Total synthesis of a novel isoprostane IPF2α-I and its identification in biological fluids
  作者：Mustafa Adiyaman、John A. Lawson、Seong-Woo Hwang、Subhash P. Khanapure、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/0040-4039(96)00973-2

  日期：1996.7

  The first total synthesis of IPF2α-I 25 is described using D-glucose as starting material. This novel isoprostane has been used to establish its presence in human urine.

  以D-葡萄糖为起始原料描述了IPF2α- I 25的第一全合成。该新型异前列腺素已用于确定其在人尿液中的存在。
• Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA
  作者：Camille Oger、Valérie Bultel-Poncé、Alexandre Guy、Thierry Durand、Jean-Marie Galano

  DOI：10.1002/ejoc.201200070

  日期：2012.5

  been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid-bound polyunsaturated fatty acids (PUFA), adrenic acid and eicosapentaenoic acid, respectively. Of special interest are the F2-dihomo-isoprostanes because they could represent potential biomarkers for myelin damage as its main PUFA constituent is adrenic acid. Our strategy, based on a pivotal enantiomerically

  已经合成了富含对映异构体的 F2-二高异前列腺素和 F3 异前列腺素。此类化合物分别源自活性氧对磷脂结合的多不饱和脂肪酸 (PUFA)、肾上腺酸和二十碳五烯酸的作用。特别令人感兴趣的是 F2-二高异前列腺素，因为它们可以代表髓鞘损伤的潜在生物标志物，因为其主要 PUFA 成分是肾上腺酸。我们的策略基于关键的对映异构体富集中间体，首次允许访问 F2-dihomo-IsoP 和 5-F3t-IsoP 的两个 C5 差向异构体。
• Total Synthesis of the Isoketal 5-D₂-IsoK Natural Product Based on Organocatalysis
  作者：Mathieu Candy、Thierry Durand、Jean-Marie Galano、Camille Oger

  DOI：10.1002/ejoc.201601301

  日期：2016.12

  The enantioselective total synthesis of the highly reactive isoketal 5-D2-IsoK was accomplished. The synthesis involved construction of the isoketal core by an organocatalyzed Michael addition between ideally functionalized aldehyde and nitroolefin partners with good enantioselectivity. The lateral chains were branched through Horner–Wadsworth-Emmons and Wittig olefinations to provide flexibility,

  完成了高反应性异缩酮 5-D2-IsoK 的对映选择性全合成。该合成涉及通过有机催化迈克尔加成在理想官能化的醛和硝基烯烃伙伴之间构建异缩酮核，具有良好的对映选择性。侧链通过 Horner-Wadsworth-Emmons 和 Wittig 烯化支化以提供灵活性，而最终的脱保护和氧化步骤在温和条件下进行，以避免已知的外消旋化和/或非常敏感的异缩酮降解。
• Polyene synthesis. Ready construction of retinol-carotene fragments, (.+-.)-6(E)-LTB3 leukotrienes, and corticrocin
  作者：Ernest Wenkert、Ming Guo、Rodolfo Lavilla、Barry Porter、Kishore Ramachandran、Jyh Horng Sheu

  DOI：10.1021/jo00312a031

  日期：1990.12
• A new approach to the synthesis of polyunsaturated deuterated isoprostanes: Total synthesis of d4-5-epi-8,12-iso-iPF3α-VI and d4-8,12-iso-iPF3α-VI
  作者：Chih-Tsung Chang、Pranav Patel、Vivek Gore、Wen-Liang Song、John A. Lawson、William S. Powell、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1016/j.bmcl.2009.09.099

  日期：2009.12

  The total and stereospecific synthesis of d(4)-5-epi-8,12-iso-iPF(3 alpha)-VI 55 and d(4)-8,12-iso-iPF(3 alpha)-VI 64, EPA-derived all-syn-isoprostanes (iPs), has been accomplished. Because of issues related to volatility and yield with some of the primary deuterated synthons an improved synthesis is presented. These two deuterated analogs were used to discover and quantify the presence of the corresponding endogenous isoprostanes in human urine. These assays may serve as a valuable index of oxidative stress in population with omega-3 fatty acid enriched diets containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and may also be useful as an index of the severity of inflammatory diseases such as atherosclerosis and Alzheimer's disease. (C) 2009 Elsevier Ltd. All rights reserved.