1-methyl-3-(methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyrano-6-yl)imidazolium iodide | 1254939-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-3-(methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyrano-6-yl)imidazolium iodide
• CAS: 1254939-69-9
• 化学式: C₃₂H₃₁N₂O₈*I
• 分子量: 698.511
• InChiKey: ARPDDBDNYAQVBV-FLGOSNSHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106.17
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  silver(l) oxide 、 1-methyl-3-(methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyrano-6-yl)imidazolium iodide 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

  摘要：

  The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

  DOI：

  10.1002/ejoc.202400177
• 作为产物：
  描述：

  methyl 6-iodo-6-deoxy-α-D-glucopyranoside 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 27.0h， 生成 1-methyl-3-(methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-D-glucopyrano-6-yl)imidazolium iodide
  参考文献：
  名称：

  Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

  摘要：

  The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

  DOI：

  10.1002/ejoc.202400177

文献信息

• Glucopyranoside-Incorporated N-Heterocyclic Carbene Complexes of Silver(I) and Palladium(II): Efficient Water-Soluble Suzuki−Miyaura Coupling Palladium(II) Catalysts
  作者：Chien-Chan Yang、Pei-Syuan Lin、Fu-Chen Liu、Ivan J. B. Lin、Gene-Hsian Lee、Shie-Ming Peng

  DOI：10.1021/om100751r

  日期：2010.11.22

  silver(I) bis(carbene) complexes have been prepared through the reactions of silver oxide with related imidazolium salts. The palladium(II) bis(carbene) complexes were synthesized from their corresponding silver(I) complexes via the technique of transmetalation. In solution, both trans-anti and trans-syn rotamers are observed for these square-planar Pd(II) complexes. In the solid state, the complex [1-methyl-3-(methyl

  通过氧化银与相关的咪唑鎓盐的反应，已经制备了含有葡糖吡喃糖苷的银（I）双（卡宾）配合物。钯（II）双（卡宾）配合物是通过相应的银（I）配合物通过金属转移技术合成的。在溶液中，这两种反式-反式和反式-顺式旋转异构体都观察到这些正方形平面的Pd（II）配合物。在固态下，配合物[1-甲基-3-（甲基2,3,4-三-O-苯甲酰基-6-脱氧-α- d-吡喃吡喃-6-基）咪唑-2-亚甲基] 2 PdBr 2采用反式构象，而配合物[1-乙基-3-（甲基2,3,4-三-O-苯甲酰基-6-脱氧-α- d-吡喃葡萄糖-6-基）咪唑-2-亚烷基] 2 PdBr 2和[1-正丁基-3-（甲基2,3,4-三-O-苯甲酰基-6-脱氧-α- d-吡喃葡萄糖- 6-基）咪唑-2-亚基] 2 PdBr 2具有反式-顺式构象。最后两个反式-syn-化合物中两个吡喃葡萄糖苷基团之间的空间拥挤可能通过咪唑环的倾斜和柔性CH 2的