(1R,6S,7S,8R,9R,10R,15S,16S,17R,18R)-7,9,16,18-tetramethoxy-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosane | 886552-59-6

• 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: (1R,6S,7S,8R,9R,10R,15S,16S,17R,18R)-7,9,16,18-tetramethoxy-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosane
• CAS: 886552-59-6
• 化学式: C₃₄H₅₀N₂O₈
• 分子量: 614.78
• InChiKey: DLGCBGUOAYJYQB-ICLOLNSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  97.9
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1R,6S,7S,8R,9R,10R,15S,16S,17R,18R)-7,9,16,18-tetramethoxy-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosane 、 2-chloro-N-(4,6-dihydropyren-1-yl)acetamide 在 四丁基碘化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以29%的产率得到N-pyren-1-yl-2-[(1R,6S,7S,8R,9R,10R,15S,16S,17R,18R)-7,9,16,18-tetramethoxy-12-[2-oxo-2-(pyren-1-ylamino)ethyl]-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosan-3-yl]acetamide
  参考文献：
  名称：

  Synthesis of Bispyrenyl Sugar-Aza-Crown Ethers as New Fluorescent Molecular Sensors for Cu(II)

  摘要：

  Two N-pyrenylacetamide-substituted sugar-aza-crown ethers have been synthesized as new fluorescent chemosensors. The designed ligands 1 and 2 exhibit fluorescence characteristics of a pyrene monomer and a dynamic excimer emission when compared to N-pyrenylacetamide as a model compound. Both ligands displayed a Cu2+-sensitive fluorescence quenching with a 1:1 stoichiometry and high stability constants (log K = 6.7 for 1 and 7.8 for 2). The quenching effect was rationalized on the basis of photoinduced electron transfer from the excited pyrene to the complexed Cu2+ cation, while the changes in excimer-to-monomer ratio were explained by a conformational analysis through DFT calculations. The predicted structure suggests that the Cu2+ cation is coordinated with the two carbonyl groups and the sugar-aza-crown ethers which rigidified the complex structure and placed the two pyrene moieties far apart.

  DOI：

  10.1021/jo070315y
• 作为产物：
  描述：

  (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxy-β-D-glucopyranosyl)-acetaldehyde 在 polymer-bound diphenylphosphine 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 64.0h， 生成 (1R,6S,7S,8R,9R,10R,15S,16S,17R,18R)-7,9,16,18-tetramethoxy-8,17-bis(phenylmethoxy)-19,20-dioxa-3,12-diazatricyclo[13.3.1.16,10]icosane
  参考文献：
  名称：

  De Novo Synthesis of Sugar-Aza-Crown Ethers via a Domino Staudinger Aza-Wittig Reaction

  摘要：

  A short and highly efficient route to sugar-aza-crown (SAC) ethers has been developed. The key step of the transformation is a one-pot cyclodimerization of C-glycosyl azido aldehydes via a domino Staudinger aza-Wittig reaction. This process allows the preparation of various orthogonally protected SAC ethers, from both alpha- and beta-C-glycosyl azido aldehydes.

  DOI：

  10.1021/jo052489q