Tris[3,5-bis[(dimethylamino)methyl]phenyl]-sulfidophosphanium | 587874-36-0

• 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: Tris[3,5-bis[(dimethylamino)methyl]phenyl]-sulfidophosphanium
• 英文别名: tris[3,5-bis[(dimethylamino)methyl]phenyl]-sulfidophosphanium
• CAS: 587874-36-0
• 化学式: C₃₆H₅₇N₆PS
• 分子量: 636.929
• InChiKey: SPNMZKJZNYHPAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-二苄氧基苄溴 、 Tris[3,5-bis[(dimethylamino)methyl]phenyl]-sulfidophosphanium 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到
  参考文献：
  名称：

  Design and synthesis of tris[bis(benzylammonium)aryl]phosphines with bulky meta-substituents

  摘要：

  A novel 3,5,3',5,3",5"-hexakis(dimethylamino)methyl substituted triphenylphosphine analogue has been prepared. The six amine functionalities of the corresponding phosphine oxide and sulfide were alkylated quantitatively with methyl iodide and benzyl bromide, as well as with G I and G2 Frechet dendrons to afford the respective hexa-ammonium triarylphosphine oxides and sulfides. The phosphine sulfide derivatives were deprotected with P(n-Bu)3 to afford a series of hexa-ammonium triarylphosphines that range from small molecules to first and second generation dendrimers (MW up to 5451.44). Upon formation of the hexa-ammonium salt a clear shift in P-31 NMR is observed, indicative for opening of the C-P-C angle of the triaryl phosphine. Calculations on the hexacationic phosphines show an increased barrier of rotation around the P-C(aryl) bond with increasing size of the N-substituents. The calculated structure of the G2-dendron alkylated hexa-ammonium triarylphosphine shows that this dendritic phosphine has a disc-like rather than a cone-like structure, with an estimated cone angle of approximately 180degrees (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00467-8
• 作为产物：
  描述：

  1-bromo-3,5-bis[(dimethylamino)methyl]benzene 在 叔丁基锂 、 sulfur 作用下， 以 二硫化碳 、 乙醚 、 正戊烷 为溶剂， 反应 17.0h， 生成 Tris[3,5-bis[(dimethylamino)methyl]phenyl]-sulfidophosphanium
  参考文献：
  名称：

  Design and synthesis of tris[bis(benzylammonium)aryl]phosphines with bulky meta-substituents

  摘要：

  A novel 3,5,3',5,3",5"-hexakis(dimethylamino)methyl substituted triphenylphosphine analogue has been prepared. The six amine functionalities of the corresponding phosphine oxide and sulfide were alkylated quantitatively with methyl iodide and benzyl bromide, as well as with G I and G2 Frechet dendrons to afford the respective hexa-ammonium triarylphosphine oxides and sulfides. The phosphine sulfide derivatives were deprotected with P(n-Bu)3 to afford a series of hexa-ammonium triarylphosphines that range from small molecules to first and second generation dendrimers (MW up to 5451.44). Upon formation of the hexa-ammonium salt a clear shift in P-31 NMR is observed, indicative for opening of the C-P-C angle of the triaryl phosphine. Calculations on the hexacationic phosphines show an increased barrier of rotation around the P-C(aryl) bond with increasing size of the N-substituents. The calculated structure of the G2-dendron alkylated hexa-ammonium triarylphosphine shows that this dendritic phosphine has a disc-like rather than a cone-like structure, with an estimated cone angle of approximately 180degrees (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00467-8

文献信息

• Design and synthesis of tris[bis(benzylammonium)aryl]phosphines with bulky meta-substituents
  作者：Robert Kreiter、Robertus J.M Klein Gebbink、Gerard van Koten

  DOI：10.1016/s0040-4020(03)00467-8

  日期：2003.5

  A novel 3,5,3',5,3",5"-hexakis(dimethylamino)methyl substituted triphenylphosphine analogue has been prepared. The six amine functionalities of the corresponding phosphine oxide and sulfide were alkylated quantitatively with methyl iodide and benzyl bromide, as well as with G I and G2 Frechet dendrons to afford the respective hexa-ammonium triarylphosphine oxides and sulfides. The phosphine sulfide derivatives were deprotected with P(n-Bu)3 to afford a series of hexa-ammonium triarylphosphines that range from small molecules to first and second generation dendrimers (MW up to 5451.44). Upon formation of the hexa-ammonium salt a clear shift in P-31 NMR is observed, indicative for opening of the C-P-C angle of the triaryl phosphine. Calculations on the hexacationic phosphines show an increased barrier of rotation around the P-C(aryl) bond with increasing size of the N-substituents. The calculated structure of the G2-dendron alkylated hexa-ammonium triarylphosphine shows that this dendritic phosphine has a disc-like rather than a cone-like structure, with an estimated cone angle of approximately 180degrees (C) 2003 Elsevier Science Ltd. All rights reserved.