12-[2-(4-Hydroxymetyl-2-methoxyphenoxy)ethoxy]-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol | 347894-49-9

• 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: 12-[2-(4-Hydroxymetyl-2-methoxyphenoxy)ethoxy]-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol
• 英文别名: 19-[2-[4-(Hydroxymethyl)-2-methoxyphenoxy]ethoxy]-6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12-diol；19-[2-[4-(hydroxymethyl)-2-methoxyphenoxy]ethoxy]-6,13,20-trimethoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12-diol
• CAS: 347894-49-9
• 化学式: C₃₄H₃₆O₉
• 分子量: 588.654
• InChiKey: NFZSFFRQUAQXRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  12-[2-(4-Hydroxymetyl-2-methoxyphenoxy)ethoxy]-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol 在 甲酸 、 caesium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成
  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
• 作为产物：
  描述：

  cyclotriguaiacyclene 、 [4-(2-碘乙氧基)-3-甲氧基苯基]甲醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以30%的产率得到12-[2-(4-Hydroxymetyl-2-methoxyphenoxy)ethoxy]-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol
  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

• Xe@cryptophane Complexes with C2 Symmetry: Synthesis and Investigations by 129Xe NMR of the Consequences of the Size of the Host Cavity for Xenon Encapsulation
  作者：Thierry Brotin、Jean-Pierre Dutasta

  DOI：10.1002/ejoc.200390153

  日期：2003.3

  at 278 K) than that observed with cryptophane-A (K = 3900 M−1). The free and bound guests were observed at room temperature under slow-exchange conditions on the 129Xe NMR timescale. A linear relationship was observed between the binding constants and the internal volume of the hosts. Under the same conditions, the Xe@cryptophane-224 [Xe3] complex underwent a fast-exchange process on the NMR timescale

  新的cryptophanes-223 (1)、-233 (2) 和-224 (3) 具有C2 对称性，带有连接两个环三戊四烯单元的不同接头，是按照多步程序合成的。通过 129Xe NMR 光谱研究了氙@cryptophane 配合物的形成。Cryptophanes-223 (1) 和 -233 (2) 在 1,1,2,2-[D2] 四氯乙烷溶液中有效地复合氙气，结合常数稍低（K 在 278 K 时分别为 2810 M-1 和 810 M-1） ) 比用cryptophane-A (K = 3900 M-1) 观察到的。在 129Xe NMR 时间尺度上的缓慢交换条件下，在室温下观察游离和结合客体。在结合常数和宿主的内部体积之间观察到线性关系。在同等条件下，Xe@cryptophane-224 [Xe3] 复合物在 NMR 时间尺度上经历了快速交换过程。解络合活化能 Ea 以及相关参数 ΔH‡
• 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.