diisopropyl (4-methoxyphenyl)phosphonate | 106052-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diisopropyl (4-methoxyphenyl)phosphonate
• 英文别名: diisopropyl (p-methoxyphenyl)phosphonate；Dipropan-2-yl (4-methoxyphenyl)phosphonate；1-di(propan-2-yloxy)phosphoryl-4-methoxybenzene
• CAS: 106052-22-6
• 化学式: C₁₃H₂₁O₄P
• 分子量: 272.281
• InChiKey: NWOWOKMXNCRIGW-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  342.1±25.0 °C(Predicted)
• 密度：
  1.0911 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  diisopropyl (4-methoxyphenyl)phosphonate 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids

  摘要：

  A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the chirality at the C-3 and P atoms, the compound with a (R,R)-configuration both at the C-3 position and the phosphorus atom was found to be potently active, while the other diastereomeric isomers were almost inactive. A number of (R,R)-compounds synthesized here exhibited broad spectrum activities with nanomolar K-i values against MMP-1, -3, -9, and TACE and also showed nanomolar IC50 values against HB-EGF shedding in a cell-based inhibition assay. The modeling study using X-ray structure of MMP-3 suggested the possible binding mode of the phosphonamide-based inhibitors.

  DOI：

  10.1021/jm0103211
• 作为产物：
  描述：

  di-isopropyl p-methoxyphenylphosphonite 在 水 、 7,7,8,8-四氰基对苯二醌二甲烷 作用下， 以 乙腈 为溶剂， 以100%的产率得到diisopropyl (4-methoxyphenyl)phosphonate
  参考文献：
  名称：

  Hall, C. D.; Beer, P. D.; Powell, R. L., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 105, # 1-4, p. 145 - 156

  摘要：

  DOI：

文献信息

• Cu/ <scp>Picolinamides‐Catalyzed</scp> Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite ^†
  作者：Chao Fang、Bangguo Wei、Dawei Ma

  DOI：10.1002/cjoc.202100354

  日期：2021.11

  Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3—5 mol% CuI and ligands were required to ensure coupling with a number of (hetero)aryl bromides and iodides to complete at 120 oC in 10—20 h.

  一些 4-羟基-吡啶甲酸衍生的酰胺被揭示为更有效的配体，用于（杂）芳基卤化物与仲氧化膦和亚磷酸酯的铜催化偶联。仅需要 3-5 mol% CuI 和配体即可确保与许多（杂）芳基溴化物和碘化物的偶联在 120 o C 下在 10-20 小时内完成。
• A mild electroassisted synthesis of (hetero)arylphosphonates
  作者：Stéphane Sengmany、Anthony Ollivier、Erwan Le Gall、Eric Léonel

  DOI：10.1039/c8ob00500a

  日期：——

  electrochemically-assisted synthesis of (hetero)arylphosphonates from (hetero)aryl halides and dimethyl phosphite is described. Very mild and simple conditions are employed as the cross-coupling is carried out in galvanostatic mode, in an undivided cell at room temperature, using NiBr2bpy as the easily available pre-catalyst and acetonitrile as the solvent. In addition, both aryl bromides and iodides can be used

  描述了由（杂）芳基卤化物和亚磷酸二甲酯的电化学辅助合成（杂）芳基膦酸酯。使用非常温和和简单的条件，因为在室温下，在未分格的电池中，以恒电流模式进行交叉偶联，使用NiBr 2 bpy作为容易获得的预催化剂，并使用乙腈作为溶剂。另外，也可以使用芳基溴化物和碘化物，以通常良好的产率提供相应的（杂）芳基膦酸酯。提出了一种涉及Niate络合物原位生成的机理。
• First reusable ligand-free palladium catalyzed C–P bond formation of aryl halides with trialkylphosphites in neat water
  作者：Nasser Iranpoor、Habib Firouzabadi、Khashayar Rajabi Moghadam、Somayeh Motavalli

  DOI：10.1039/c4ra07680j

  日期：——

  of aryl iodides, bromides and chlorides with trialkylphosphites is described for the first time in neat water. The aryl phosphonates are obtained in good to excellent yields. The reaction can be also performed with Ni(II) with longer reaction time. The role of tetrabutylammonium bromide in this reaction as reducing agent for generation of Pd(0) at room temperature is also demonstrated. Pd(0)/TBAB was

  首次在纯净水中描述了可重用的无配体钯催化的芳基碘，溴化物和氯化物与亚磷酸三烷基酯的膦酸酯化反应。以良好至优异的产率获得芳基膦酸酯。该反应也可以用Ni（II）以更长的反应时间进行。还证明了四丁基溴化铵在该反应中作为在室温下生成Pd（0）的还原剂的作用。Pd（0）/ TBAB可以轻松地重复使用三遍，而不会降低效率。
• Nickel-Catalyzed Phosphorylation of Phenol Derivatives via C–O/P–H Cross-Coupling
  作者：Jia Yang、Jing Xiao、Tieqiao Chen、Li-Biao Han

  DOI：10.1021/acs.joc.6b00289

  日期：2016.5.6

  An efficient nickel-catalyzed phosphorylation of phenol derivatives with P(O)–H compounds via C–O/P–H cross-coupling is described. Under the reaction conditions, various phenyl pivalates coupled readily with hydrogen phosphoryl compounds to afford the corresponding coupling products aryl phosphonates and aryl phosphine oxides in good to high yields.

  描述了通过C-O / P-H交叉偶联将苯酚衍生物与P（O）-H化合物进行有效的镍催化磷酸化反应。在反应条件下，各种新戊酸苯基酯容易与氢磷酰基化合物偶合，从而以高至高收率得到相应的偶合产物芳基膦酸酯和芳基膦氧化物。
• General Oxidative Aryl C–P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds
  作者：Jianyu Dong、Long Liu、Xuyu Ji、Qian Shang、Lixin Liu、Lebin Su、Bing Chen、Ruifeng Kan、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/acs.orglett.9b00922

  日期：2019.5.3

  Oxidative C–C/P–H cross-coupling is achieved via Pd-catalyzed decarbonylative cross-coupling of aroylhydrazides with P(O)H compounds. The unique cooperative reaction system, especially the Brønsted acid and bidentate phosphine ligand, allows the selective activation of the inert C–C bond and the suppression of the undesired oxidation and coordination of >P(O)–H compounds, leading to a general oxidative

  氧化的C / C / P-H交叉偶联是通过Pd催化的酰肼与P（O）H化合物的脱羰交叉偶联而实现的。独特的协同反应系统，特别是布朗斯台德酸和双齿膦配体，可以选择性活化惰性碳键，并抑制> P（O）–H化合物的不希望的氧化和配位，从而导致一般的氧化反应从容易获得的底物中合成芳基磷化合物。