2,7,12-Trimethoxy-3,8,13-tris{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclonenene | 347894-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,7,12-Trimethoxy-3,8,13-tris{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclonenene
• 英文别名: 2-[[3-Methoxy-4-[2-[[6,13,20-trimethoxy-12,19-bis[2-[2-methoxy-4-(oxan-2-yloxymethyl)phenoxy]ethoxy]-5-tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaenyl]oxy]ethoxy]phenyl]methoxy]oxane
• CAS: 347894-45-5
• 化学式: C₆₉H₈₄O₁₈
• 分子量: 1201.42
• InChiKey: MHCQLBGDVFZSOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  87
• 可旋转键数：
  30
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2,7,12-Trimethoxy-3,8,13-tris{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclonenene 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以51%的产率得到cryptophane-A
  参考文献：
  名称：

  Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst

  摘要：

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.

  DOI：

  10.1021/jo050495g
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 4-甲基苯磺酸吡啶 、 potassium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 18.0h， 生成 2,7,12-Trimethoxy-3,8,13-tris{2-[2-methoxy-4-(tetrahydropyran-2-yloxymethyl)phenoxy]ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclonenene
  参考文献：
  名称：

  Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe@Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments

  摘要：

  We present the synthesis of a series of deuterated cryptophanes 2-6 by a slightly modified procedure used for cryptophane-A. We show that for [Xe@cryptophane] complexes the use of variable-temperature one-dimensional 129Xe magnetization transfer (1D-EX-SY) allows the measurement of exchange rates. From these data the decomplexation activation energy Ea has been estimated to be 37.5+/-2 kJ mol(-1). The decomplexation activation enthalpy, deltaH(++) = 35.5+/-2 kJ mol(-1), and entropy, deltaS(++) = -60+/-5 J mol(-1) K(-1), have also been calculated. The calculated negative activation entropy suggests that the activated complex associated with decomplexation is conformationally more strained than the complex in its ground state.

  DOI：

  10.1002/1521-3765(20010401)7:7<1561::aid-chem1561>3.0.co;2-9

文献信息

• Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst
  作者：Thierry Brotin、Vincent Roy、Jean-Pierre Dutasta

  DOI：10.1021/jo050495g

  日期：2005.8.1

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.
• Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe@Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments
  作者：Thierry Brotin、Thomas Devic、Anne Lesage、Lyndon Emsley、André Collet

  DOI：10.1002/1521-3765(20010401)7:7<1561::aid-chem1561>3.0.co;2-9

  日期：2001.4.1

  We present the synthesis of a series of deuterated cryptophanes 2-6 by a slightly modified procedure used for cryptophane-A. We show that for [Xe@cryptophane] complexes the use of variable-temperature one-dimensional 129Xe magnetization transfer (1D-EX-SY) allows the measurement of exchange rates. From these data the decomplexation activation energy Ea has been estimated to be 37.5+/-2 kJ mol(-1). The decomplexation activation enthalpy, deltaH(++) = 35.5+/-2 kJ mol(-1), and entropy, deltaS(++) = -60+/-5 J mol(-1) K(-1), have also been calculated. The calculated negative activation entropy suggests that the activated complex associated with decomplexation is conformationally more strained than the complex in its ground state.