6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol | 1254581-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
• 英文别名: 6,12-diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
• CAS: 1254581-02-6
• 化学式: C₇₂H₆₂O₈P₂S₂
• 分子量: 1181.36
• InChiKey: RWNDASBVSXTNME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.2
• 重原子数：
  84
• 可旋转键数：
  14
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以56%的产率得到6,12-Dioxido-6,12-diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
  参考文献：
  名称：

  Restricted Guest Tumbling in Phosphorylated Self-Assembled Capsules

  摘要：

  ABii diphosphonatocavitands self-assemble in chloroform solution to form dimeric molecular capsules. The molecular capsules can incarcerate an N-methylpyridinium or N-methylpicolinium guest. We have demonstrated that the supramolecular assembly acts as a molecular rotor as a result of the restricted motion of the guest inside the molecular cavity. In the solid state, X-ray diffraction analysis of the free host showed that two cavitands interact through strong hydrogen bonds to give the supramolecular self-assembled capsule. The solid-state structure of the N-methylpicolinium complex is comparable to that of the free host and indicates that the guest is not a prerequisite for the formation of the capsule. DOSY NMR studies provided a definitive argument for the formation of the free and complexed supramolecular capsule in CDCl3 solution. In solution, the tumbling of the N-methylpyridinium and N-methylpicolinium guests about the equatorial axes of the host can be frozen and differs by the respective energy barriers, with the larger picolinium substrate having a larger value (Delta G(double dagger) = 69.7 kJ mol(-1)) than the shorter pyridinium guest (Delta G(double dagger) = 44.8 kJ mol(-1)). This behavior corresponds to the restricted rotation of a rotator in a supramolecular rotor.

  DOI：

  10.1021/ja104388t
• 作为产物：
  描述：

  tetraphenylethylresorcin[4]arene 、 苯基二氯化磷 在 吡啶 、 sulfur 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以5%的产率得到6,12-Diphenyl-20,24,27,33-tetrakis(2-phenylethyl)-6,12-disulfido-5,7,11,13-tetraoxa-6,12-diphosphoniaheptacyclo[15.9.7.128,32.04,25.08,23.010,21.014,19]tetratriaconta-1(26),2,4(25),8,10(21),14(19),15,17,22,28(34),29,31-dodecaene-2,16,29,31-tetrol
  参考文献：
  名称：

  Restricted Guest Tumbling in Phosphorylated Self-Assembled Capsules

  摘要：

  ABii diphosphonatocavitands self-assemble in chloroform solution to form dimeric molecular capsules. The molecular capsules can incarcerate an N-methylpyridinium or N-methylpicolinium guest. We have demonstrated that the supramolecular assembly acts as a molecular rotor as a result of the restricted motion of the guest inside the molecular cavity. In the solid state, X-ray diffraction analysis of the free host showed that two cavitands interact through strong hydrogen bonds to give the supramolecular self-assembled capsule. The solid-state structure of the N-methylpicolinium complex is comparable to that of the free host and indicates that the guest is not a prerequisite for the formation of the capsule. DOSY NMR studies provided a definitive argument for the formation of the free and complexed supramolecular capsule in CDCl3 solution. In solution, the tumbling of the N-methylpyridinium and N-methylpicolinium guests about the equatorial axes of the host can be frozen and differs by the respective energy barriers, with the larger picolinium substrate having a larger value (Delta G(double dagger) = 69.7 kJ mol(-1)) than the shorter pyridinium guest (Delta G(double dagger) = 44.8 kJ mol(-1)). This behavior corresponds to the restricted rotation of a rotator in a supramolecular rotor.

  DOI：

  10.1021/ja104388t

文献信息

• Restricted Guest Tumbling in Phosphorylated Self-Assembled Capsules
  作者：Steven Harthong、Béatrice Dubessy、Jérôme Vachon、Christophe Aronica、Jean-Christophe Mulatier、Jean-Pierre Dutasta

  DOI：10.1021/ja104388t

  日期：2010.11.10

  ABii diphosphonatocavitands self-assemble in chloroform solution to form dimeric molecular capsules. The molecular capsules can incarcerate an N-methylpyridinium or N-methylpicolinium guest. We have demonstrated that the supramolecular assembly acts as a molecular rotor as a result of the restricted motion of the guest inside the molecular cavity. In the solid state, X-ray diffraction analysis of the free host showed that two cavitands interact through strong hydrogen bonds to give the supramolecular self-assembled capsule. The solid-state structure of the N-methylpicolinium complex is comparable to that of the free host and indicates that the guest is not a prerequisite for the formation of the capsule. DOSY NMR studies provided a definitive argument for the formation of the free and complexed supramolecular capsule in CDCl3 solution. In solution, the tumbling of the N-methylpyridinium and N-methylpicolinium guests about the equatorial axes of the host can be frozen and differs by the respective energy barriers, with the larger picolinium substrate having a larger value (Delta G(double dagger) = 69.7 kJ mol(-1)) than the shorter pyridinium guest (Delta G(double dagger) = 44.8 kJ mol(-1)). This behavior corresponds to the restricted rotation of a rotator in a supramolecular rotor.