25,26,27-triethoxy-28-hydroxy-p-tert-butylcalix<4>arene | 135193-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,26,27-triethoxy-28-hydroxy-p-tert-butylcalix<4>arene
• 英文别名: 5,11,17,23-tetratert-butyl-26,27,28-triethoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaen-25-ol
• CAS: 135193-21-4
• 化学式: C₅₀H₆₈O₄
• 分子量: 733.088
• InChiKey: DKYXFCBVNCRICT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  54
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  25,26,27-triethoxy-28-hydroxy-p-tert-butylcalix<4>arene 在 palladium on activated charcoal 硝酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 14.25h， 生成 11,17,23-tri-t-butyl-25,26,27-triethoxy-28-hydroxy-5-<1-(2,4,6-triphenylpyridinio)>calix<4>arene perchlorate
  参考文献：
  名称：

  杯[4]芳烃的新型发色吡啶鎓衍生物，I

  摘要：

  5-（1-吡啶基）-11,17,23-三叔丁基-28-羟基-25,26,27-三烷氧基杯[4]芳烃和5,17-双（1-吡啶基）-11,23已经合成了-二叔丁基-26,28-二羟基-25,27-二（乙氧基羰基）甲氧基杯[4]芳烃高氯酸盐。这些化合物充当生色团，在Li +络合时在有机溶剂中表现出光学响应。Na +和K +盐。

  DOI：

  10.1016/0040-4020(95)00914-0
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 碘乙烷 在 barium dihydroxide 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到25,26,27-triethoxy-28-hydroxy-p-tert-butylcalix<4>arene
  参考文献：
  名称：

  Conformations and structures of tetra-O-alkyl-p-tert-butylcalix[4]arenes. How is the conformation of calix[4]arenes immobilized?

  摘要：

  p-tert-Butylcalix[4]arene (1H4) was tetra-O-alkylated with alkyl halogens (RX: R = Me, Et, n-Pr, and n-Bu) in the presence of NaH as base, and the products (1R4) were analyzed by HPLC and H-1 NMR spectroscopy. It was found that (i) ring inversion is suppressed by R greater Et, (ii) the final conformer distribution in 1Pr4 and 1Bu4 is governed by the kinetic control, the main products being ''cone'' and ''partial cone'' (approximately in a 1:1 ratio), (iii) 1 Me4 mostly exists as a thermodynamically stable partial-cone conformer, and (iv) 1Et4 shows an intermediary behavior between 1Me4 and 1Pr4: it mostly exists as a partial-cone conformer but slowly isomerizes to a ''1,2-alternate'' conformer at high temperature. The X-ray crystallographic analysis of partial-cone-1Et4 was investigated. To clarify where and how the conformation of 1R4 is immobilized, we alkylated 1H4 in a stepwise manner. It was shown that when NaH is used as base, the conformation of 1Et4 is determined at the fourth ethylation step (1HEt3 --> 1Et4), whereas the conformation of 1Pr4 is determined at the third propylation step (1H2Pr2 --> 1HPr3). The conformer distribution was significantly affected by alkali and alkaline earth metal cations used as base; in particular, it is worthy of mentioning that (i) when Cs2CO3 is used as base, 1,2-alternate-1Pr4 is formed in addition to partial-cone-1Pr4 and (ii) when Ba(OH)2 is used as base, cone-1Pr4 is yielded in 100% selectivity. On the basis of these studies, we discuss how the conformation of calix[4]arenes is immobilized.

  DOI：

  10.1021/jo00016a027