2,8,14,20-Tetrakis(2-hydroxyphenyl)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-dodecaene-4,6,10,12,16,18,22,24-octol | 135269-77-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,8,14,20-Tetrakis(2-hydroxyphenyl)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-dodecaene-4,6,10,12,16,18,22,24-octol
• CAS: 135269-77-1
• 化学式: C₅₂H₄₀O₁₂
• 分子量: 856.882
• InChiKey: LGNRVQUBPUILDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  64
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  243
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  溴乙酸叔丁酯 、 2,8,14,20-Tetrakis(2-hydroxyphenyl)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-dodecaene-4,6,10,12,16,18,22,24-octol 在 四丁基溴化铵 、 caesium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 5.0h， 以39%的产率得到Tert-butyl 2-[2-[4,6,10,12,16,18,22,24-octakis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-8,14,20-tris[2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]-2-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]phenoxy]acetate
  参考文献：
  名称：

  The Synthesis and Photo-Induced Deprotection Reaction of Calix[4]resorcinarene Derivatives Containingt-Butyl Ester Moieties

  摘要：

  本研究考察了具有悬垂 t-丁基酯分子的钙并[4]间苯二酚衍生物的合成和光诱导脱保护反应。在盐酸作为催化剂的存在下，间苯二酚与某些醛在乙醇中于 80 °C 下缩合反应 30 分钟，制备了 1a-1h 钙并[4]间苯二酚衍生物，收率良好。以碳酸铯为碱，四丁基溴化铵（TBAB）为相转移催化剂，将 1a-1h 与溴乙酸叔丁酯进行取代反应，得到了相应的钙[4]间苯二酚衍生物 2a-2h，并带有悬垂的叔丁酯基团。研究发现，2a、2e、2f、2g 和 2h 具有成膜特性。在双[4-(二苯基磺酰基)苯基]硫醚（DPSP）作为光酸发生器的存在下，紫外线照射 5 分钟，然后在 170 ℃ 下加热，考察了萼片烯衍生物 2a、2e、2f、2g 和 2h 在薄膜状态下的光诱导脱保护反应。研究发现，2a、2e、2f、2g 和 2h 的 t-丁酯基团的脱保护反应进展顺利，可定量生成相应的钙烯烃衍生物 3a、3e、3f、3g 和 3h，并带有羧酸基团。

  DOI：

  10.1246/bcsj.77.819
• 作为产物：
  描述：

  邻甲基苄醇 、 间苯二酚 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以70%的产率得到2,8,14,20-Tetrakis(2-hydroxyphenyl)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-dodecaene-4,6,10,12,16,18,22,24-octol
  参考文献：
  名称：

  The Synthesis and Photo-Induced Deprotection Reaction of Calix[4]resorcinarene Derivatives Containingt-Butyl Ester Moieties

  摘要：

  本研究考察了具有悬垂 t-丁基酯分子的钙并[4]间苯二酚衍生物的合成和光诱导脱保护反应。在盐酸作为催化剂的存在下，间苯二酚与某些醛在乙醇中于 80 °C 下缩合反应 30 分钟，制备了 1a-1h 钙并[4]间苯二酚衍生物，收率良好。以碳酸铯为碱，四丁基溴化铵（TBAB）为相转移催化剂，将 1a-1h 与溴乙酸叔丁酯进行取代反应，得到了相应的钙[4]间苯二酚衍生物 2a-2h，并带有悬垂的叔丁酯基团。研究发现，2a、2e、2f、2g 和 2h 具有成膜特性。在双[4-(二苯基磺酰基)苯基]硫醚（DPSP）作为光酸发生器的存在下，紫外线照射 5 分钟，然后在 170 ℃ 下加热，考察了萼片烯衍生物 2a、2e、2f、2g 和 2h 在薄膜状态下的光诱导脱保护反应。研究发现，2a、2e、2f、2g 和 2h 的 t-丁酯基团的脱保护反应进展顺利，可定量生成相应的钙烯烃衍生物 3a、3e、3f、3g 和 3h，并带有羧酸基团。

  DOI：

  10.1246/bcsj.77.819

文献信息

• Host-guest chemistry. 27. Mechanisms of macrocycle genesis. The condensation of resorcinol with aldehydes
  作者：Frank Weinelt、Hans Joerg Schneider

  DOI：10.1021/jo00019a011

  日期：1991.9

  The title reactions proceed in high yields without high dilution techniques as long as substituents allow hydrogen bonds between the phenolic units and do not lead to steric hindrance. Isomerization rates for three epimeric cyclophanes, including a hitherto undiscovered one, are obtained by least-squares fit with integrated rate equations. The buildup sequences of oligomers, polymers, and macrocycles are analyzed by numerical stepwise integration with 50 rate constants, based on the fit of time-concentration curves of seven identified structures that were followed by proton NMR. Macrocyclization is favored by the following: (a) fast degradation of oligomers, (b) fast ring closure of tetramers, as well as (c) fast chain growth to these in comparison to ring opening. Homogeneous reaction conditions, here with methanol as solvent, are essential not only for the quantitative analyses, but also for the solubility of polymers in view of their degradation and for the observation of new stereoisomers. Molecular mechanics calculations with the CHARMm field and model considerations identify the factors responsible for the unique preference for cyclization over polymerization. Both hydrogen bonds between the phenolic units and 1.5 interactions between phenolic groups and the methyl substituent-stemming from the acetaldehyde-strongly favor folded conformers with small distances around d = 3.3-4.6 angstrom between the terminal reacting centers in comparison to stretched conformations with d = 12.2-18.3 angstrom.
• Mobinikhaledi; Kalhor; Ghorbani, Asian Journal of Chemistry, 2010, vol. 22, # 2, p. 1103 - 1106
  作者：Mobinikhaledi、Kalhor、Ghorbani、Fathinejad

  DOI：——

  日期：——
• NOLL, BERND;WEINELT, FRANK;WEINELT, HERBERT;HAUPTMANN, SIEGFRIED;MANN, GE+
  作者：NOLL, BERND、WEINELT, FRANK、WEINELT, HERBERT、HAUPTMANN, SIEGFRIED、MANN, GE+

  DOI：——

  日期：——
• PROCESS FOR PRODUCING CARBON MATERIAL
  申请人：Suzuki Junji

  公开号：US20100298522A1

  公开（公告）日：2010-11-25

  A process for producing a carbon material comprising the following steps (A) and (B): Step (A): a step of reacting a compound represented by the formula (1): wherein R represents a hydrogen atom etc., R′ represents a hydrogen atom etc., and n represents 3, 5 or 7, with an aldehyde compound to obtain a polymer, Step (B): a step of heating the polymer obtained in Step (A) at 600 to 3000° C. under an inert gas atmosphere.
• [EN] PROCESS FOR PRODUCING CARBON MATERIAL<br/>[FR] PROCÉDÉ DE FABRICATION D'UNE MATIÈRE CARBONÉE
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2009101947A2

  公开（公告）日：2009-08-20

  A process for producing a carbon material comprising the following steps (A) and (B): Step (A): a step of reacting a compound represented by the formula (1): wherein R represents a hydrogen atom etc., R' represents a hydrogen atom etc., and n represents 3, 5 or 7, with an aldehyde compound to obtain a polymer, Step (B): a step of heating the polymer obtained in Step (A) at 600 to 3000oC under an inert gas atmosphere.