5,11,17,23,29,35-hexa-p-(3-methoxycarbonylmethyl-1-adamantyl)calix[6]arene | 647832-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23,29,35-hexa-p-(3-methoxycarbonylmethyl-1-adamantyl)calix[6]arene
• 英文别名: methyl 2-[3-[37,38,39,40,41,42-hexahydroxy-11,17,23,29,35-pentakis[3-(2-methoxy-2-oxoethyl)-1-adamantyl]-5-heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15,17,19(40),21(39),22,24,27(38),28,30,33(37),34-octadecaenyl]-1-adamantyl]acetate
• CAS: 647832-71-1
• 化学式: C₁₂₀H₁₄₄O₁₈
• 分子量: 1874.45
• InChiKey: WQOYODXDGNUDOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.19
• 重原子数：
  138.0
• 可旋转键数：
  18.0
• 环数：
  31.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  279.18
• 氢给体数：
  6.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35-hexa-p-(3-methoxycarbonylmethyl-1-adamantyl)calix[6]arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到5,11,17,23,29,35-hexa-p-[3-(2-hydroxyethyl)-1-adamantyl]calix[6]arene
  参考文献：
  名称：

  摘要：

  Procedures have been developed for the preparation of completely and partially adamantylated calix[n]arenes (n = 5, 6) by reaction of 3-R-substituted 1-hydroxyadamantanes (R = H, 4-MeC(6)H(4), 4-MeSO(2)C(6)H(4),4-HO-3-HOCOC(6)H(3), HOCOCH(2)) with p-H-calix[n]arenes (n = 5, 6) and 5,11,23,29-tetra-tert-butylcalix[6]arene in trifluoroacetic acid. Lower- and upper-rim modification of the prepared compounds has been studied. According to the (1)H NMR data, adamantylcalix[6]arenes possessing carboxymethyl groups in the adamantane moieties are characterized by reduced conformational mobility.

  DOI：

  10.1023/a:1025541731033
• 作为产物：
  描述：

  甲醇 、 5,11,17,23,29,35-hexa-p-(3-carboxymethyl-1-adamantyl)calix[6]arene 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以94%的产率得到5,11,17,23,29,35-hexa-p-(3-methoxycarbonylmethyl-1-adamantyl)calix[6]arene
  参考文献：
  名称：

  摘要：

  Procedures have been developed for the preparation of completely and partially adamantylated calix[n]arenes (n = 5, 6) by reaction of 3-R-substituted 1-hydroxyadamantanes (R = H, 4-MeC(6)H(4), 4-MeSO(2)C(6)H(4),4-HO-3-HOCOC(6)H(3), HOCOCH(2)) with p-H-calix[n]arenes (n = 5, 6) and 5,11,23,29-tetra-tert-butylcalix[6]arene in trifluoroacetic acid. Lower- and upper-rim modification of the prepared compounds has been studied. According to the (1)H NMR data, adamantylcalix[6]arenes possessing carboxymethyl groups in the adamantane moieties are characterized by reduced conformational mobility.

  DOI：

  10.1023/a:1025541731033

文献信息

• Conformational Restriction of the Calix[6]arene Macrocycle by the Ritter Reaction
  作者：Ivan M. Vatsouro、Elvira A. Shokova、Alla K. Shestakova、Vyacheslav A. Chertkov、Vladimir V. Kovalev

  DOI：10.1002/ejoc.200500604

  日期：2006.1

  approach to the restriction of the conformational mobility of calix[6]arenes. The method involves the addition of tertiary alcohols to calix[6]arenes with one, three and six cyanomethoxy groups attached to the lower rim under modified Ritter reaction conditions. Alkylation of monocyanomethoxy-p-tert-butylcalix[6]arene (1) and 37,39,41-trimethoxy-38,40,42-tricyanomethoxy-p-tert-butylcalix[6]arene (2) with

  在此，我们报告了一种限制杯 [6] 芳烃构象迁移率的新型有效方法的开发。该方法包括在改进的 Ritter 反应条件下将叔醇添加到杯 [6] 芳烃中，其中一个、三个和六个氰基甲氧基连接到下边缘。单氰基甲氧基-对叔丁基杯[6]芳烃 (1) 和 37,39,41-三甲氧基-38,40,42-三氰甲氧基-对叔丁基杯[6]芳烃 (2) 与 3-R-的烷基化三氟乙酸中的 1-金刚烷醇 (R = H, CH2COOH) 得到相应的具有锥形构象的单酰胺和三酰胺。己腈衍生物的部分烷基化显示出意想不到的区域选择性。将 1-金刚烷醇或叔丁醇加成到六氰基甲氧基-pX-杯[6]芳烃 3a-c（X = 叔丁基、1-金刚烷基、3-甲氧羰基甲基-1-金刚烷基）中得到 37，40-二腈-38,39,41,42-四酰胺为主要产品。这些四酰胺在溶液中的构象限制在很宽的温度范围内，并采用扁平的 1,2,3-交替构象，如 2D 和可变温度