2-(diphenylphosphono)thiophene | 63818-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(diphenylphosphono)thiophene
• 英文别名: thiophen-2-yl-phosphonic acid diphenyl ester；2-Diphenoxyphosphorylthiophene
• CAS: 63818-46-2
• 化学式: C₁₆H₁₃O₃PS
• 分子量: 316.317
• InChiKey: KLFVRHLCPFOSSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C(Solv: ethyl ether (60-29-7); ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  431.6±27.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘噻吩 、 亚磷酸三苯酯 在 nickel dichloride 、 亚磷酸三乙酯 作用下， 反应 4.0h， 以89%的产率得到2-(diphenylphosphono)thiophene
  参考文献：
  名称：

  A concise method for synthesis of diaryl aryl- or alkylphosphonates

  摘要：

  A convenient method has been developed to synthesize diaryl arylphosphonates from triaryl phosphites, triethyl phosphite, and aromatic halides. The new method relies on the triethyl phosphite assisted nickel catalyzed Arbuzov reaction and can be applied to synthesize certain diaryl alkylphosphonates without catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.028

文献信息

• A new synthesis of π-electron conjugated phosphonates and phosphonic bis(diethylamides) and their SHG activities
  作者：Takuji Ogawa、Naoya Usuki、Noboru Ono

  DOI：10.1039/a709082j

  日期：——

  A series of vinylic and arylic phosphonates and phosphonic bis(diethylamides) were prepared by copper promoted substitution of the corresponding bromides. These π-electron conjugated phosphonates and phosphonic bis(diethylamides) were investigated to elucidate their optical and second harmonic generation (SHG) properties; it was found that diphenyl 2-(4-dimethylaminophenyl)ethenylphosphonate exhibited strong SHG activity, the efficiency being 13 times greater than that of urea.

  通过铜催化的相应溴化物的取代反应，制备了一系列乙烯基和芳基膦酸盐及双（二乙基酰胺）膦酸。研究了这些共轭的磷酸盐和双（二乙基酰胺）膦酸的光学性质和二次谐波产生（SHG）特性；发现二苯基2-（4-二甲氨基苯基）乙烯基膦酸盐具有强烈的SHG活性，效率比尿素高13倍。
• Catalyst and process for the polymerization of alpha-olefins and a process for preparing an alpha-olefin polymerization catalyst component
  申请人：Standard Oil Company

  公开号：EP0013744A1

  公开（公告）日：1980-08-06

  High activity alpha-olefin polymerization catalysts comprising an organometallic promoter and a component prepared from at least one compound of a Group IVB, VB, or VIB metal, at least one support material which is a divalent metal salt of a phosphorus acid ester having at least one phosphorus acid ester group bonded to metal through oxygen or sulfur, and at least one alkylaluminium halide.

  高活性α-烯烃聚合催化剂，包括有机金属促进剂和由至少一种 IVB、VB 或 VIB 族金属化合物制备的组分，至少一种支撑材料，该支撑材料是磷酸酯的二价金属盐，其中至少有一个磷酸酯基团通过氧或硫与金属键合，以及至少一种烷基卤化铝。
• Palladium-Catalyzed Decarbonylative Michaelis–Arbuzov Reaction of Carboxylic Acids and Triaryl Phosphites
  作者：Zhixuan Xu、Mengjie Cen、Zihan Chen、Linbin Yao、Chunya Li、Bencan Tang、Long Liu、Tianzeng Huang、Tieqiao Chen、Li-Biao Han

  DOI：10.1021/acs.orglett.4c02495

  日期：2024.8.23

  Michaelis–Arbuzov reaction of carboxylic acids and triaryl phosphites for preparing aryl phosphonates under anhydride-free conditions has been reported. In this context, triaryl phosphites serve as both reagents for activating the carboxylic acids and substrates for the reaction. There have been no reports to date of efficient and direct methods for the in situ activation of carboxylic acids using triaryl phosphites

  据报道，在无酸酐条件下，通过钯催化的羧酸和亚磷酸三芳基酯的脱羰米氏-阿布佐夫反应制备膦酸芳基酯。在本文中，亚磷酸三芳基酯既充当用于活化羧酸的试剂又充当反应的底物。迄今为止，还没有关于使用亚磷酸三芳基酯原位活化羧酸的有效且直接的方法的报道。与已知方法相比，该反应避免了有机卤化物的使用，并且对于由亚磷酸三芳基酯和羧酸合成各种膦酸芳基酯具有优异的官能团耐受性。该反应具有可扩展性，适用于合成具有生物活性片段的芳基膦酸酯。
• US4233182A
  申请人：——

  公开号：US4233182A

  公开（公告）日：1980-11-11
• US4233253A
  申请人：——

  公开号：US4233253A

  公开（公告）日：1980-11-11