磷酸二乙基(1-萘基甲基)酯 | 64050-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 磷酸二乙基(1-萘基甲基)酯
• 英文名称: diethyl (naphthalen-1-ylmethyl) phosphate
• 英文别名: Diethyl 1-naphthylmethyl phosphate；diethyl naphthalen-1-ylmethyl phosphate
• CAS: 64050-53-9
• 化学式: C₁₅H₁₉O₄P
• 分子量: 294.287
• InChiKey: DSUPAEWIYDJKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  磷酸二乙基(1-萘基甲基)酯 在 palladium diacetate 、 间氯过氧苯甲酸 、 4-(二甲氨基)三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (4-allylnaphthalen-1-yl)methanol
  参考文献：
  名称：

  Pd催化磷酸苄酯的脱芳基化

  摘要：

  已经开发出苄基磷酸的脱芳香族C–C键形成。在钯/ PAr 3催化剂的存在下，磷酸苄酯与硼酸烯丙酯反应，以脱芳族方式生成烯丙基化产物。产生的脱芳烃分子已通过Simmons-Smith环丙烷化和氧化作用成功衍生。

  DOI：

  10.1021/acs.orglett.8b01807
• 作为产物：
  描述：

  diethyl hydroxy(naphthalen-1-yl)methylphosphonate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以69%的产率得到磷酸二乙基(1-萘基甲基)酯
  参考文献：
  名称：

  Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids

  摘要：

  Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The K(i) values of these compounds are as low as 4 mu M, the lowest reported to date for a PAP inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.125

文献信息

• Suzuki−Miyaura Cross-Coupling of Benzylic Phosphates with Arylboronic Acids
  作者：Mark McLaughlin

  DOI：10.1021/ol0517271

  日期：2005.10.1

  [reaction: see text] Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids was investigated. Optimum conditions employed the simple catalytic system of palladium(II) acetate (1 mol %) and triphenylphosphine (4 mol %) with either potassium phosphate or potassium carbonate as the base and toluene as the solvent at 90 degrees C. Using the developed conditions, a series of structurally

  [反应：见正文]研究了苄基磷酸酯与芳基硼酸的Suzuki-Miyaura交叉偶联。最佳条件是在90摄氏度下，以磷酸钾或碳酸钾为基础，甲苯为溶剂的乙酸钯（II）（1 mol％）和三苯膦（4 mol％）的简单催化体系。制备了一系列结构上不同的二芳基甲烷。
• Benzylic Phosphates in Friedel–Crafts Reactions with Activated and Unactivated Arenes: Access to Polyarylated Alkanes
  作者：Gangaram Pallikonda、Manab Chakravarty

  DOI：10.1021/acs.joc.5b02441

  日期：2016.3.4

  Easily reachable electron-poor/rich primary and secondary benzylic phosphates are suitably used as substrates for Friedel–Crafts benzylation reactions with only 1.2 equiv activated/deactivated arenes (no additional solvent) to access structurally and electronically diverse polyarylated alkanes with excellent yields and selectivities at room temperature. Specifically, diversely substituted di/triarylmethanes

  易于获得的电子贫乏/富集的伯和仲苄基磷酸酯适合用作Friedel-Crafts苄基化反应的底物，仅需1.2当量的活化/失活芳烃（无需额外的溶剂）即可获得结构和电子多样的多芳基化烷烃，收率和选择性很好。室内温度。特别是，使用此方法可在2-30分钟内生成不同取代的二/三芳基甲烷。只需调节磷酸盐，即可通过此途径轻松实现大量贫电子的聚芳基烷烃。
• Photochemistry of phosphate esters: an efficient method for the generation of electrophiles
  作者：Richard S. Givens、Bogdan Matuszewski

  DOI：10.1021/ja00334a075

  日期：1984.10

  The photochemical cleavage of benzyl diethyl phosphates has been examined in tert-butyl alcohol, which produces the corresponding benzyl tert-butyl ether as the major solvolysis product upon direct irradiation. The multiplicity of the reactive excited state has been established as the singlet state

  已经在叔丁醇中检测了磷酸苄基二乙酯的光化学裂解，在直接照射下产生相应的苄基叔丁基醚作为主要的溶剂分解产物。反应激发态的多重性已被确定为单线态
• Formation of New Phosphates from Aldehydes by a DBU-Catalysed Phospha-Brook Rearrangement in a Polar Solvent
  作者：Laurent El Kaïm、Laetitia Gaultier、Laurence Grimaud、Aurélie Dos Santos

  DOI：10.1055/s-2005-872670

  日期：——

  different possible reaction pathways depending on the solvent used. Apolar solvents give the normal Pudovik adduct, whereas the use of DBU in a polar solvent allows the formation of a phosphate ester via phospha-Brook rearrangement of the intermediate hydroxyphosphonate.

  通过用碱处理将二烷基亚磷酸酯加成到芳族醛（Pudovik 反应）会导致两种不同的可能反应途径，具体取决于所使用的溶剂。非极性溶剂产生正常的 Pudovik 加合物，而在极性溶剂中使用 DBU 允许通过中间体羟基膦酸酯的磷酸-布鲁克重排形成磷酸酯。
• Synthesis of Diarylmethanes through Palladium-Catalyzed Coupling of Benzylic Phosphates with Arylsilanes
  作者：Guo Tang、Pengbo Zhang、Jian Xu、Yuzhen Gao、Xueqin Li、Yufen Zhao

  DOI：10.1055/s-0034-1379366

  日期：——

  An efficient approach to the benzylation of arenes has been developed. The reactions described provide straightforward access to diarylmethanes through Pd-catalyzed coupling of benzylic phosphates with arylsilanes in good to excellent yields. The reaction tolerates a wide range of functionalities such as halide, alkoxyl, and nitro groups.