[10,12,22,24-Tetrahydroxy-2,8,14,20-tetramethyl-6,16,18-tris[(2,4,6-trimethylphenyl)sulfonyloxy]-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl] 2,4,6-trimethylbenzenesulfonate | 172508-76-8

• 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: [10,12,22,24-Tetrahydroxy-2,8,14,20-tetramethyl-6,16,18-tris[(2,4,6-trimethylphenyl)sulfonyloxy]-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl] 2,4,6-trimethylbenzenesulfonate
• CAS: 172508-76-8
• 化学式: C₆₈H₇₂O₁₆S₄
• 分子量: 1273.57
• InChiKey: JJPBKQGTOQEOJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  88
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  288
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4'-chlorosulfonylbenzo-15-crown-5 、 [10,12,22,24-Tetrahydroxy-2,8,14,20-tetramethyl-6,16,18-tris[(2,4,6-trimethylphenyl)sulfonyloxy]-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl] 2,4,6-trimethylbenzenesulfonate 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, Conformation, and Binding Properties of Resorcarene Tetrasulfonates. Asymmetric Reorganization of Pendant Sulfonyl Groups via Intramolecular SO- - -H−O Hydrogen Bonds

  摘要：

  The regioselective reaction of resorcarene octaols 1 with 4 equiv of arylsulfonyl chlorides and Et3N in MeCN gives in 30-60% yield the C-2v symmetrical tetrasulfonates 3. The mild electrophilic substitution (aminomethylation, bromination) of resorcarene tetrasulfonates 3 and tetraphosphates 2 takes place only in the 2-positions of unsubstituted resorcinol rings yielding distally disubstituted resorcarenes 4. The acylation of hydroxy groups in compounds 2 and 3 gives C-2v symmetrical octaesters 5 including large resorcarene tetracrown-ethers. In the minimized boat conformation of tetrasulfonates 3 the two unsubstituted resorcinol rings are vertical and the sulfonyl fragments are arranged in a C-2 symmetrical manner via intramolecular S=O- - -H-O hydrogen bonds. This structure is proved by NMR and IR spectroscopy. In the case of tetrasulfonate 3c the two enantiomeric conformations interconvert in CDCl3 with Delta G* = 11.6 kcal/mol. This is in agreement with the Delta E* value predicted by molecular mechanics in vacuo.

  DOI：

  10.1021/jo981751a
• 作为产物：
  描述：

  4,6,16,18-tetrahydroxy-10,12,22,24-tetrakis(p-tolylsulfonyloxy)-2,8-14,20-(tetramethyl)calix<4>arene 在 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 12.0h， 生成 [10,12,22,24-Tetrahydroxy-2,8,14,20-tetramethyl-6,16,18-tris[(2,4,6-trimethylphenyl)sulfonyloxy]-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl] 2,4,6-trimethylbenzenesulfonate
  参考文献：
  名称：

  Synthesis, Conformation, and Binding Properties of Resorcarene Tetrasulfonates. Asymmetric Reorganization of Pendant Sulfonyl Groups via Intramolecular SO- - -H−O Hydrogen Bonds

  摘要：

  The regioselective reaction of resorcarene octaols 1 with 4 equiv of arylsulfonyl chlorides and Et3N in MeCN gives in 30-60% yield the C-2v symmetrical tetrasulfonates 3. The mild electrophilic substitution (aminomethylation, bromination) of resorcarene tetrasulfonates 3 and tetraphosphates 2 takes place only in the 2-positions of unsubstituted resorcinol rings yielding distally disubstituted resorcarenes 4. The acylation of hydroxy groups in compounds 2 and 3 gives C-2v symmetrical octaesters 5 including large resorcarene tetracrown-ethers. In the minimized boat conformation of tetrasulfonates 3 the two unsubstituted resorcinol rings are vertical and the sulfonyl fragments are arranged in a C-2 symmetrical manner via intramolecular S=O- - -H-O hydrogen bonds. This structure is proved by NMR and IR spectroscopy. In the case of tetrasulfonate 3c the two enantiomeric conformations interconvert in CDCl3 with Delta G* = 11.6 kcal/mol. This is in agreement with the Delta E* value predicted by molecular mechanics in vacuo.

  DOI：

  10.1021/jo981751a

文献信息

• Selective Acylation of Calixresorcinolarene
  作者：Oleg V. Lukin、Vladimir V. Pirozhenko、Alexander N. Shivanyuk

  DOI：10.1016/0040-4039(95)01573-z

  日期：1995.10

  Selective acylation of calixresorcinalarene 1 has been performed. The reaction with mild acylating agents such as arylsulfanylchlorides leads to the tetrasubstituted compounds. Stereochemistry of the compounds obtained has been investigated in detail by means of H-1- and C-13-NMR.
• Rigid Tetranitroresorcinarenes
  作者：Alexander Shivanyuk、Adel Rafai Far、Julius Rebek

  DOI：10.1021/ol025725h

  日期：2002.5.1

  o-Alkylation of C-2v-symmetrical resorcinarene tetraesters 2 with 2 equiv of 1,3-difluoro-4,6-dinitrobenzene readily affords conformationally rigid octanitro resorcinarene 3, which is a potential scaffold for the design of supramolecular structures.
• Synthesis, Conformation, and Binding Properties of Resorcarene Tetrasulfonates. Asymmetric Reorganization of Pendant Sulfonyl Groups via Intramolecular SO- - -H−O Hydrogen Bonds
  作者：Oleg Lukin、Alexander Shivanyuk、Vladimir V. Pirozhenko、Ivan F. Tsymbal、Vitaly I. Kalchenko

  DOI：10.1021/jo981751a

  日期：1998.12.1

  The regioselective reaction of resorcarene octaols 1 with 4 equiv of arylsulfonyl chlorides and Et3N in MeCN gives in 30-60% yield the C-2v symmetrical tetrasulfonates 3. The mild electrophilic substitution (aminomethylation, bromination) of resorcarene tetrasulfonates 3 and tetraphosphates 2 takes place only in the 2-positions of unsubstituted resorcinol rings yielding distally disubstituted resorcarenes 4. The acylation of hydroxy groups in compounds 2 and 3 gives C-2v symmetrical octaesters 5 including large resorcarene tetracrown-ethers. In the minimized boat conformation of tetrasulfonates 3 the two unsubstituted resorcinol rings are vertical and the sulfonyl fragments are arranged in a C-2 symmetrical manner via intramolecular S=O- - -H-O hydrogen bonds. This structure is proved by NMR and IR spectroscopy. In the case of tetrasulfonate 3c the two enantiomeric conformations interconvert in CDCl3 with Delta G* = 11.6 kcal/mol. This is in agreement with the Delta E* value predicted by molecular mechanics in vacuo.