4-(diphenylphosphino)benzyltrimethylammonium bromide | 1229444-43-2

• 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: 4-(diphenylphosphino)benzyltrimethylammonium bromide
• 英文别名: 4-(Diphenylphosphino)benzyl trimethyl ammonium bromide；(4-diphenylphosphanylphenyl)methyl-trimethylazanium;bromide
• CAS: 1229444-43-2
• 化学式: Br*C₂₂H₂₅NP
• 分子量: 414.325
• InChiKey: SCOPNFOKKTUMIX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  正溴丁烷 、 4-(diphenylphosphino)benzyltrimethylammonium bromide 以 1,2-二氯乙烷 为溶剂， 反应 50.0h， 以95%的产率得到
  参考文献：
  名称：

  Wittig reaction with ion-supported Ph3P

  摘要：

  Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding alpha,beta-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4'-chlorophenyl)-2-propenoate and 1 -(4'-chlorophenyl)-2-(4 ''-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.111
• 作为产物：
  描述：

  4-溴-N,N-二甲基苄胺 在 双氧水 、 magnesium 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 5.0h， 生成 4-(diphenylphosphino)benzyltrimethylammonium bromide
  参考文献：
  名称：

  离子负载的Ph 3 P可轻松地由羧酸和胺制备酰胺

  摘要：

  离子负载的Ph 3 P，4-（二苯基膦基）苄基三甲基溴化铵（IS-Ph 3 P）可用于在溴三氯甲烷存在下将多种羧酸与胺轻松酰胺化，从而提供相应的酰胺产量。在本反应中，通过用二乙醚或氯仿简单萃取反应混合物，然后从萃取物中除去溶剂，以高收率和高纯度获得所需酰胺。另外，在本还原缩合反应中作为IS-Ph 3 P的副产物的离子担载的Ph 3 PO（IS-Ph 3 PO）被高收率回收，可以还原为IS-Ph 3。P用于在相同的酰胺化羧酸中重复使用。

  DOI：

  10.1016/j.tet.2013.03.021
• 作为试剂：
  描述：

  胡椒酸 、 苄胺 在 三氯溴甲烷 、 4-(diphenylphosphino)benzyltrimethylammonium bromide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以93%的产率得到N-benzylbenzo[d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  离子负载的Ph 3 P可轻松地由羧酸和胺制备酰胺

  摘要：

  离子负载的Ph 3 P，4-（二苯基膦基）苄基三甲基溴化铵（IS-Ph 3 P）可用于在溴三氯甲烷存在下将多种羧酸与胺轻松酰胺化，从而提供相应的酰胺产量。在本反应中，通过用二乙醚或氯仿简单萃取反应混合物，然后从萃取物中除去溶剂，以高收率和高纯度获得所需酰胺。另外，在本还原缩合反应中作为IS-Ph 3 P的副产物的离子担载的Ph 3 PO（IS-Ph 3 PO）被高收率回收，可以还原为IS-Ph 3。P用于在相同的酰胺化羧酸中重复使用。

  DOI：

  10.1016/j.tet.2013.03.021

文献信息

• Novel preparation of ion-supported triphenylphosphines and their synthetic utility
  作者：Yumi Imura、Naoya Shimojuh、Yuhta Kawano、Hideo Togo

  DOI：10.1016/j.tet.2010.03.039

  日期：2010.5

  Novel ion-supported Ph3P compounds, 4-(diphenylphosphino)- benzyltrimethylammonium bromide (A) and N-methyl-N-[4-(diphenylphosphino) -benzyl]pyrrolidinium bromide (B), were prepared. Because of their stability in air, ion-supported Ph3P A and B could be used for the halogenation of alcohols, the esterification of carboxylic acid with the Mitsunobu reaction, the Mizoroki–Heck reaction, and the Sonogashira

  制备了新型的离子负载型Ph 3 P化合物4-（二苯基膦基）-苄基三甲基溴化铵（A）和N-甲基-N- [4-（二苯基膦基）-苄基]吡咯烷溴化物（B）。由于其在空气中的稳定性，离子负载的Ph 3 P A和B可用于醇的卤化，Mitsunobu反应，Mizuroki-Heck反应和Sonogashira反应的羧酸酯化反应。使用这些离子负载的Ph 3 P A和B的优点是由于其在醚中的溶解度差而通过醚萃取分离产物的简单方法，以及通过高收率（> 90％）过滤而易于回收副产物离子负载的Ph 3 PO的方法，该方法可以再生并将其重复用于相同的反应，如醇的卤化反应和用Mitsunobu反应进行的羧酸酯化反应。另一方面，使用碘代甲苯，可以将含有Pd（OAc）2或PdCl 2以及离子负载的Ph 3 P A或B作为催化剂的离子液体反应介质用于相同的Mizoroki-Heck反应和Sonogashira反应，以保持较高的收率。分别与丙烯酸甲酯和苯乙炔。
• Facile preparation of amides from carboxylic acids and amines with ion-supported Ph3P
  作者：Yuhsuke Kawagoe、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2013.03.021

  日期：2013.5

  rimethylammonium bromide (IS-Ph3P), could be used for the facile amidation of a wide range of carboxylic acids with amines in the presence of bromotrichloromethane to provide the corresponding amides in good yields. In the present reaction, the desired amides were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether or chloroform and subsequent removal

  离子负载的Ph 3 P，4-（二苯基膦基）苄基三甲基溴化铵（IS-Ph 3 P）可用于在溴三氯甲烷存在下将多种羧酸与胺轻松酰胺化，从而提供相应的酰胺产量。在本反应中，通过用二乙醚或氯仿简单萃取反应混合物，然后从萃取物中除去溶剂，以高收率和高纯度获得所需酰胺。另外，在本还原缩合反应中作为IS-Ph 3 P的副产物的离子担载的Ph 3 PO（IS-Ph 3 PO）被高收率回收，可以还原为IS-Ph 3。P用于在相同的酰胺化羧酸中重复使用。
• Wittig reaction with ion-supported Ph3P
  作者：Naoya Shimojuh、Yumi Imura、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2010.11.111

  日期：2011.2

  Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding alpha,beta-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4'-chlorophenyl)-2-propenoate and 1 -(4'-chlorophenyl)-2-(4 ''-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate. (C) 2010 Elsevier Ltd. All rights reserved.