2-<6-(benzyloxy)hexyl>propane-1,3-diol bis(4-methylbenzenesulfonate) | 1025840-23-6

• 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: 2-<6-(benzyloxy)hexyl>propane-1,3-diol bis(4-methylbenzenesulfonate)
• 英文别名: 2-[6-(benzyloxy)hexyl]propane-1,3-diol bis(4-methylbenzenesulfonate)；[2-[(4-Methylphenyl)sulfonyloxymethyl]-8-phenylmethoxyoctyl] 4-methylbenzenesulfonate
• CAS: 1025840-23-6
• 化学式: C₃₀H₃₈O₇S₂
• 分子量: 574.76
• InChiKey: CEQBHTVSJLBXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,10-二氮杂-12-冠4-醚 、 2-<6-(benzyloxy)hexyl>propane-1,3-diol bis(4-methylbenzenesulfonate) 在 sodium perchlorate 、 sodium carbonate 作用下， 生成 、
  参考文献：
  名称：

  Synthesis and Properties of New Lipophilic Macrotricyclic Cylindrical Cryptands

  摘要：

  Cylindrical cryptands 2a-c, in which two 1,7-dioxa-4,10-diazacyclododecane rings are connected by two equally substituted propylene bridges, have been obtained in appreciable yields by a ''one-pot'' synthesis. The assembling of the macrotricyclic structure is likely driven by the template effect of metal cations. These compounds, both as free receptors or as complexes, exist as cis and trans diastereoisomers, which do not interconvert and have been separated and characterized by X-ray analysis. The extraction constants (K-e) of cryptands 2 for alkali picrates under CHCl3/H2O and solid/liquid two-phase conditions have been measured by UV-vis spectrophotometry. The complexation behavior of cryptands 2 has been rationalized analyzing the preorganization of binding sites in the minimum energy conformations obtained by molecular mechanics calculations. Minimum energy conformations have been calculated also for the previously reported cryptands 1 and have been compared with those of 2. Results fit reasonably well with those of X-ray structures.

  DOI：

  10.1021/jo00125a025
• 作为产物：
  描述：

  6-(苄氧基)-1-己醇 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 87.0h， 生成 2-<6-(benzyloxy)hexyl>propane-1,3-diol bis(4-methylbenzenesulfonate)
  参考文献：
  名称：

  Synthesis and Properties of New Lipophilic Macrotricyclic Cylindrical Cryptands

  摘要：

  Cylindrical cryptands 2a-c, in which two 1,7-dioxa-4,10-diazacyclododecane rings are connected by two equally substituted propylene bridges, have been obtained in appreciable yields by a ''one-pot'' synthesis. The assembling of the macrotricyclic structure is likely driven by the template effect of metal cations. These compounds, both as free receptors or as complexes, exist as cis and trans diastereoisomers, which do not interconvert and have been separated and characterized by X-ray analysis. The extraction constants (K-e) of cryptands 2 for alkali picrates under CHCl3/H2O and solid/liquid two-phase conditions have been measured by UV-vis spectrophotometry. The complexation behavior of cryptands 2 has been rationalized analyzing the preorganization of binding sites in the minimum energy conformations obtained by molecular mechanics calculations. Minimum energy conformations have been calculated also for the previously reported cryptands 1 and have been compared with those of 2. Results fit reasonably well with those of X-ray structures.

  DOI：

  10.1021/jo00125a025

文献信息

• Synthesis and Properties of New Lipophilic Macrotricyclic Cylindrical Cryptands
  作者：Silvio Quici、Amedea Manfredi、Laura Raimondi、Angelo Sironi

  DOI：10.1021/jo00125a025

  日期：1995.10

  Cylindrical cryptands 2a-c, in which two 1,7-dioxa-4,10-diazacyclododecane rings are connected by two equally substituted propylene bridges, have been obtained in appreciable yields by a ''one-pot'' synthesis. The assembling of the macrotricyclic structure is likely driven by the template effect of metal cations. These compounds, both as free receptors or as complexes, exist as cis and trans diastereoisomers, which do not interconvert and have been separated and characterized by X-ray analysis. The extraction constants (K-e) of cryptands 2 for alkali picrates under CHCl3/H2O and solid/liquid two-phase conditions have been measured by UV-vis spectrophotometry. The complexation behavior of cryptands 2 has been rationalized analyzing the preorganization of binding sites in the minimum energy conformations obtained by molecular mechanics calculations. Minimum energy conformations have been calculated also for the previously reported cryptands 1 and have been compared with those of 2. Results fit reasonably well with those of X-ray structures.