4-(((diethoxyphosphoryl)oxy)methyl)phenyl acetate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(((diethoxyphosphoryl)oxy)methyl)phenyl acetate
• 英文别名: 4-acetyloxybenzyl diethylphosphate；4-Acetyloxybenzyl Diethyl Phosphate；[4-(diethoxyphosphoryloxymethyl)phenyl] acetate
• 化学式: C₁₃H₁₉O₆P
• 分子量: 302.264
• InChiKey: CXYWKPRLDZUCEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 4-(((diethoxyphosphoryl)oxy)methyl)phenyl acetate 在 锰 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以39%的产率得到methyl 4-(2-oxo-2-phenylethyl)benzoate
  参考文献：
  名称：

  由卤化苄，磺酸盐和磷酸盐直接制备苄基锰试剂及其反应：在有机合成中的应用

  摘要：

  研究了通过Rieke方法制备的高活性锰（Mn）*用于直接制备苄基锰试剂的方法。高活性锰在苄基卤化物中的氧化加成反应很容易在温和的条件下完成。此外，通过将Mn *直接氧化加成到苄基磺酸盐和磷酸盐的碳-氧键上来制备苄基锰磺酸盐和磷酸盐。发现所得的苄基锰试剂与多种亲电试剂发生交叉偶联反应。这些反应大多数在温和条件下在不存在任何过渡金属催化剂的情况下进行。此外，还研究了使用高活性锰制备不含过渡金属催化剂的功能化苄基卤化物的均偶联产物。N-烷氧基羰基吡啶鎓盐。

  DOI：

  10.1016/s0022-328x(03)00500-x
• 作为产物：
  描述：

  4-乙酰氧基苄醇 、 氯磷酸二乙酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到4-(((diethoxyphosphoryl)oxy)methyl)phenyl acetate
  参考文献：
  名称：

  Synthesis and biological activity of acetyl-protected hydroxybenzyl diethyl phosphates (EHBP) as potential chemotherapeutic agents

  摘要：

  Several acetyl-protected hydroxybenzyl diethyl phosphates (EHBPs) that are capable of forming quinone methide intermediates were synthesized and their cell growth inhibitory properties were evaluated in four different human cancer cell lines. Compounds 1, 1a, and 1b, corresponding to (4-acetyloxybenzyl diethylphosphate), (3-methyl-4-acetyloxybenzyl diethylphosphate), and (3-chloro-4-acetyloxybenzyl diethylphosphate), were significantly more potent than compounds 2 and 3, (2-acetyloxybenzyl diethylphosphate) and (3-acetyloxybenzyl diethylphosphate), respectively. Using HT-29 human colon cancer cells, compounds 1 and 3 increased apoptosis, inhibited proliferation, and caused a G(2)/M block in the cell cycle. Our data suggest that these compounds merit further investigation as potential anti-cancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.075

文献信息

• Anti-Inflammatory Compounds and Uses Thereof
  申请人：Rigas Basil

  公开号：US20090099137A1

  公开（公告）日：2009-04-16

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also described.
• ANTI-INFLAMMATORY COMPOUNDS AND USES THEREOF
  申请人：RIGAS Basil

  公开号：US20120316139A1

  公开（公告）日：2012-12-13

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also disclosed.
• Anti-Inflammatory Compounds and Use Thereof
  申请人：Rigas Basil

  公开号：US20160243137A1

  公开（公告）日：2016-08-25

  Compounds of the general formula are disclosed with activity towards treating diseases related to inflammation, such as cancer, neurodegenerative and cardiovascular diseases. Pharmaceutical compositions and methods of use are also disclosed.
• US8236820B2
  申请人：——

  公开号：US8236820B2

  公开（公告）日：2012-08-07
• Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: applications in organic synthesis
  作者：YoungSung Suh、Jun-sik Lee、Seoung-Hoi Kim、Reuben D Rieke

  DOI：10.1016/s0022-328x(03)00500-x

  日期：2003.11

  The use of highly active manganese (Mn)*, prepared by the Rieke method, was investigated for the direct preparation of benzylic manganese reagents. The oxidative addition of the highly active manganese to benzylic halides was easily completed under mild conditions. Moreover, benzylic manganese sulfonates and phosphates were prepared by direct oxidative addition of Mn* to the carbon–oxygen bonds of

  研究了通过Rieke方法制备的高活性锰（Mn）*用于直接制备苄基锰试剂的方法。高活性锰在苄基卤化物中的氧化加成反应很容易在温和的条件下完成。此外，通过将Mn *直接氧化加成到苄基磺酸盐和磷酸盐的碳-氧键上来制备苄基锰磺酸盐和磷酸盐。发现所得的苄基锰试剂与多种亲电试剂发生交叉偶联反应。这些反应大多数在温和条件下在不存在任何过渡金属催化剂的情况下进行。此外，还研究了使用高活性锰制备不含过渡金属催化剂的功能化苄基卤化物的均偶联产物。N-烷氧基羰基吡啶鎓盐。