4,6,10,12,16,18,22,24-octacarboxymethoxy-2,8,14,20-tetramethylpentacyclo<19.3.1.1^3,7,1^9,13,1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-docecaene | 156617-63-9

• 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: 4,6,10,12,16,18,22,24-octacarboxymethoxy-2,8,14,20-tetramethylpentacyclo<19.3.1.1^3,7,1^9,13,1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-docecaene
• 英文别名: C-methyl-calix[4]resorcinarene octacarboxylate；4,6,10,12,16,18,22,24-octacarboxymethoxy-2,8,14,20-tetramethylpentacyclo[19.3.1.1^3,7,1^9,13,1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-docecaene；2-[[6,10,12,16,18,22,24-Heptakis(carboxymethoxy)-2,8,14,20-tetramethyl-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]oxy]acetic acid
• CAS: 156617-63-9；130508-38-2
• 化学式: C₄₈H₄₈O₂₄
• 分子量: 1008.89
• InChiKey: FAFXHWFJNHITSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  372
• 氢给体数：
  8
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  甲醇 、 4,6,10,12,16,18,22,24-octacarboxymethoxy-2,8,14,20-tetramethylpentacyclo<19.3.1.1^3,7,1^9,13,1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-docecaene 在 硫酸 作用下， 生成 Methyl 2-[[6,10,12,16,18,22,24-heptakis(2-methoxy-2-oxoethoxy)-2,8,14,20-tetramethyl-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]oxy]acetate
  参考文献：
  名称：

  Singh, Serjinder; Singh, Harmit; Sharma, Lalit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 428 - 431

  摘要：

  DOI：
• 作为产物：
  描述：

  Tert-butyl 2-[[2,8,14,20-tetramethyl-6,10,12,16,18,22,24-heptakis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-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]oxy]acetate 在 bis-[4-(diphenylsulfonio)phenyl] sulfide 作用下， 以 氯仿 为溶剂， 生成 4,6,10,12,16,18,22,24-octacarboxymethoxy-2,8,14,20-tetramethylpentacyclo<19.3.1.1^3,7,1^9,13,1^15,19>octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-docecaene
  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

• Synthesis of Novel Chemically Amplified Materials Based on Calix[4]arene Derivatives with Acetal Moieties
  作者：Hiroto Kudo、Kouji Mitani、Syuhei Koyama、Tadatomi Nishikubo

  DOI：10.1246/bcsj.77.2109

  日期：2004.11

  The synthesis and photoinduced deprotection reaction of calix[4]resorcinarene derivatives with pendant acetal moieties were examined. C-methyl[(methoxymethylcarbonyl)oxy]calix[4]resorcinarene (CRA-Acetal) and C-4-hydroxyphenyl[(methoxymethylcarbonyl)oxy]calix[4]resorcinarene (CRAph-Acetal) were prepared from C-methylcalix[4]resorcinarene (CRA) and C-4-hydroxyphenylcalix[4]resorcinarene (CRAph). The synthesized CRA-Acetal and CRAph-Acetal had good solubilities, good film-forming properties, and high thermal stabilities. The photoinduced deprotection reaction of CRA-Acetal and CRAph-Acetal was examined in the presence of bis[4-(diphenylsulfonio)phenyl]sulfide (DPSP) as a photo-acid generator in the film state upon UV irradiation. It was found that the deprotection reaction of acetal groups of CRA-Acetal and CRAph-Acetal proceeded smoothly without further heating to produce the corresponding calixarene derivatives, CRA-COOH and CRAph-COOH with carboxylic acid groups.

  研究了带有乙缩醛侧基的杯[4]萘并芘衍生物的合成和光诱导脱保护反应。通过C-甲基杯[4]萘并芘（CRA）和C-4-羟基苯基杯[4]萘并芘（CRAph）制备了C-甲基[(甲氧基甲基羰基)氧基]杯[4]萘并芘（CRA-乙缩醛）和C-4-羟基苯基[(甲氧基甲基羰基)氧基]杯[4]萘并芘（CRAph-乙缩醛）。合成的CRA-乙缩醛和CRAph-乙缩醛具有良好的溶解性、成膜性和热稳定性。在双[4-(二苯基硫鎓)苯基]硫醚（DPSP）作为光酸产生剂存在的情况下，研究了CRA-乙缩醛和CRAph-乙缩醛的光诱导脱保护反应。研究发现，CRA-乙缩醛和CRAph-乙缩醛的乙缩醛基团的脱保护反应顺利进行，无需进一步加热即可生成相应的带有羧酸基团的杯芳烃衍生物CRA-COOH和CRAph-COOH。
• Four coordination polymers constructed by a novel octacarboxylate functionalized calix[4]arene ligand: syntheses, structures, and photoluminescence property
  作者：Hang Zhang、Wei Jiang、Jin Yang、Ying-Ying Liu、Shuyan Song、Jian-Fang Ma

  DOI：10.1039/c4ce01581a

  日期：——

  Four novel coordination polymers, [(CH3)2NH2][Zn3(HL)(H2O)2]·4H2O (1), [Co4(L)(DMF)2(H2O)8]·6H2O (2), [Ni4(L)(DMF)2(H2O)8]·6H2O (3) and [(CH3)2NH2][Mn3(HL)(DMF)(H2O)6]·6H2O (4) (H8L = 2,8,14,20-tetra-methyl-4,6,10,12,16,18,22,24-octa-carboxymethoxy-calix[4]arene and DMF = N,N-dimethylformamide) have been synthesized. Their structures have been confirmed and further characterized by relative physical methods. Compound 1 reveals a 2D double layer. Compounds 2 and 3 are isomorphous, and demonstrate identical 3D (3,6)-connecting nets with (42·6)(44·62·88·10) topologies. Compound 4 features a 3D binodal 5-connected (46·64)(46·64) framework. The UV-vis spectra of compounds 1–4 have been explored. The solid-state luminescence of compound 1 and its fluorescence property in various suspensions has also been investigated at room temperature. Moreover, the luminescence sensing properties of 1 for nitroaromatic compounds have been studied in detail.

  四种新型配位聚合物：[(CH3)2NH2][Zn3(HL)(H2O)2]-4H2O (1)、[Co4(L)(DMF)2(H2O)8]-6H2O (2)、[Ni4(L)(DMF)2(H2O)8]-6H2O (3)和[(CH3)2NH2][Mn3(HL)(DMF)(H2O)6]-6H2O (4) （H8L = 2、8,14,20-四甲基-4,6,10,12,16,18,22,24-八羧甲氧基-萼[4]炔，DMF = N,N-二甲基甲酰胺）的合成。它们的结构已得到确认，并通过相关物理方法得到进一步表征。化合物 1 显示了二维双层结构。化合物 2 和 3 是同构物，具有相同的三维 (3,6) 连接网，拓扑结构为 (42-6)(44-62-88-10)。化合物 4 采用了三维二极 5 连接 (46-64)(46-64) 框架。对化合物 1-4 的紫外可见光谱进行了研究。还研究了化合物 1 在室温下的固态发光及其在各种悬浮液中的荧光特性。此外，还详细研究了 1 对硝基芳香族化合物的发光传感特性。
• The Synthesis and Photo-Induced Deprotection Reaction of Calix[4]resorcinarene Derivatives Containing<i>t</i>-Butyl Ester Moieties
  作者：Hiroto Kudo、Kouji Mitani、Tadatomi Nishikubo、Masaya Mitsuishi、Tokuji Miyashita

  DOI：10.1246/bcsj.77.819

  日期：2004.4

  The syntheses and photoinduced deprotection reactions of calix[4]resorcinarene derivatives with pendant t-butyl ester moieties were examined. Calix[4]resorcinarenes, 1a–1h, were prepared by the condensation reaction of resorcinol with certain aldehydes in the presence of hydrochloric acid as a catalyst in ethanol at 80 °C for 30 min in good yields. The substitution reaction of 1a–1h with t-butyl bromoacetate using cesium carbonate as a base and tetrabutylammmonium bromide (TBAB) as a phase transfer catalyst was performed to afford the corresponding calix[4]resorcinarene derivatives, 2a–2h with pendant t-butyl ester groups. It was found that 2a, 2e, 2f, 2g, and 2h had film forming properties. The photo-induced deprotection reaction of calixarene derivatives 2a, 2e, 2f, 2g, and 2h was examined in the presence of bis-[4-(diphenylsulfonio)phenyl] sulfide (DPSP) as a photoacid generator in the film state upon UV irradiation for 5 min followed by heating at 170 °C. It was found that the deprotection reaction of the t-butyl ester groups of 2a, 2e, 2f, 2g, and 2h proceeded smoothly to produce the corresponding calixarene derivatives, 3a, 3e, 3f, 3g, and 3h with carboxylic acid groups, quantitatively.

  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。
• Singh, Serjinder; Singh, Harmit; Sharma, Lalit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 428 - 431
  作者：Singh, Serjinder、Singh, Harmit、Sharma, Lalit

  DOI：——

  日期：——