1-(10'-(3-hydroxypropyl)-3',3',5',5'-tetramethoxyspiro[piperidine-4,2'-4,8,12,16-tetraoxa-1,3,9,11(1,4)-tetrabenzenacyclohexadecaphan]-1-yl)ethan-1-one | 577994-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(10'-(3-hydroxypropyl)-3',3',5',5'-tetramethoxyspiro[piperidine-4,2'-4,8,12,16-tetraoxa-1,3,9,11(1,4)-tetrabenzenacyclohexadecaphan]-1-yl)ethan-1-one
• CAS: 577994-64-0
• 化学式: C₄₅H₅₅NO₁₀
• 分子量: 769.932
• InChiKey: NVDGTVHGZJXADF-UHFFFAOYSA-N

物化性质

• 熔点：
  83-85 °C
• 沸点：
  886.8±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  56.0
• 可旋转键数：
  7.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  114.38
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(10'-(3-hydroxypropyl)-3',3',5',5'-tetramethoxyspiro[piperidine-4,2'-4,8,12,16-tetraoxa-1,3,9,11(1,4)-tetrabenzenacyclohexadecaphan]-1-yl)ethan-1-one 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以87%的产率得到
  参考文献：
  名称：

  Host−[2]Rotaxanes as Cellular Transport Agents

  摘要：

  Host-[2)rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K-A's) in the range of 1 x 10(4) to 5 x 104 M-1, whereas the K-A range for the fluorophores is 1 x 10(4) to 9 x 10(5) m(-1). Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 x 10(3) to 5 x 10(3) m(-1) range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft-[2)rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.

  DOI：

  10.1021/ja034918c
• 作为产物：
  描述：

  3,3-bis[4-(benzyloxy)phenyl]propan-1-ol 在 10% palladium on active carbon 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 80.0~100.0 ℃ 、344.74 kPa 条件下， 反应 72.0h， 生成 1-(10'-(3-hydroxypropyl)-3',3',5',5'-tetramethoxyspiro[piperidine-4,2'-4,8,12,16-tetraoxa-1,3,9,11(1,4)-tetrabenzenacyclohexadecaphan]-1-yl)ethan-1-one
  参考文献：
  名称：

  Host−[2]Rotaxanes as Cellular Transport Agents

  摘要：

  Host-[2)rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K-A's) in the range of 1 x 10(4) to 5 x 104 M-1, whereas the K-A range for the fluorophores is 1 x 10(4) to 9 x 10(5) m(-1). Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 x 10(3) to 5 x 10(3) m(-1) range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane-[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft-[2)rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.

  DOI：

  10.1021/ja034918c