ortho-xylenyl phosphoryl chloride | 49785-01-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: ortho-xylenyl phosphoryl chloride
• 英文别名: o-xylenylphosphorylchloride；3-Chloro-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepine 3-oxide；3-chloro-1,5-dihydro-2,4,3λ5-benzodioxaphosphepine 3-oxide
• CAS: 49785-01-5
• 化学式: C₈H₈ClO₃P
• 分子量: 218.576
• InChiKey: JVVKBEGGHBHTDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  ortho-xylenyl phosphoryl chloride 在 triphenylphosphine-carbon tetrachloride 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  A simple synthesis of dimeric 2,2-disubstituted 1,3, 2-benzoxazaphosholes from phosphoryl pIV-compounds.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98072-9
• 作为产物：
  描述：

  邻苯二甲醇 在 三氯氧磷 作用下， 生成 ortho-xylenyl phosphoryl chloride
  参考文献：
  名称：

  Eu（fod）3诱导七元环磷酸酯的3 J HP变异和构象变化

  摘要：

  借助于Eu（）（3）（3- ）1,3-二氢-2,4,3-苯并二氧杂膦酸3-氧化物（1）建立了两种椅子形式（2a）和（2b）之间的构象平衡。fod）3，这引起了3 J HP的大变化，这归因于轴向磷酰基构象体的增加。

  DOI：

  10.1039/c39730000494

文献信息

• Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides – towards kinase-like reactivity
  作者：James I. Murray、Rudiger Woscholski、Alan C. Spivey

  DOI：10.1039/c4cc05388e

  日期：——

  The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.

  描述了由2-芳基-4-（二甲基氨基）吡啶-N-氧化物催化的磷酰氯对含羟基的氨基酸衍生物和多元醇的化学选择性磷酸化。
• Chemical Synthesis of <scp>d</scp>-<i>glycero</i>-<scp>d</scp>-<i>manno</i>-Heptose 1,7-Bisphosphate and Evaluation of Its Ability to Modulate NF-κB Activation
  作者：Shinsuke Inuki、Toshihiko Aiba、Shota Kawakami、Taishin Akiyama、Jun-ichiro Inoue、Yukari Fujimoto

  DOI：10.1021/acs.orglett.7b01158

  日期：2017.6.16

  and glycolipids. HBP β-anomer was recently reported to be a pathogen-associated molecular pattern (PAMP) that regulates TIFA-dependent immunity. Herein, we report the chemical synthesis of HBP α- and β-anomers, which highlights a C-7 carbon homologation via the Corey–Chaykovsky reaction, and the introduction of a phosphate group at the anomeric position using the Mitsunobu reaction. Furthermore, NF-κB

  d -甘油基- d -甘露-Heptose 1,7-二磷酸（HBP）是庚糖残基的前体在革兰氏阴性细菌膜表面糖蛋白和糖脂中。最近报道，HBPβ-异头物是一种病原体相关分子模式（PAMP），可调节TIFA依赖性免疫。在这里，我们报道了HBPα-和β-端基异构体的化学合成，该反应突出了通过Corey-Chaykovsky反应的C-7碳同系物，以及使用Mitsunobu反应在端基异构体位置引入了磷酸基团。此外，NF-κB报告基因检测表明，HBPβ-异头物激活了NF-κB信号传导途径。
• Organocatalytic Phosphorylation of Alcohols Using Pyridine-N-oxide
  作者：Alan Spivey、James Murray、Rudiger Woscholski

  DOI：10.1055/s-0034-1379993

  日期：——

  Phosphorylation of alcohols by phosphoryl chlorides catalysed by pyridine-N-oxide is reported. The utility of this method is demonstrated through phosphorylation of primary, secondary and a tertiary alcohol as well as phenols under mild reaction conditions and with low catalyst loading (5 mol%).
• Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
  作者：Alexander M. Sherwood、Adam L. Halberstadt、Adam K. Klein、John D. McCorvy、Kristi W. Kaylo、Robert B. Kargbo、Poncho Meisenheimer

  DOI：10.1021/acs.jnatprod.9b01061

  日期：2020.2.28

  A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.
• ANALOGUES SYNTHETIQUES DES PHOSPHATIDYL-MYO-INOSITOL MANNOSIDES POURVUS D'UNE ACTIVITE INHIBITRICE DE LA REPONSE INFLAMMATOIRE.
  申请人：Centre National de la Recherche Scientifique (C.N.R.S)

  公开号：EP2280986A2

  公开（公告）日：2011-02-09