11,23-Di-tert-butyl-5,17-dichloro-25,26,27,28-tetrahydroxycalix<4>arene | 127679-84-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 11,23-Di-tert-butyl-5,17-dichloro-25,26,27,28-tetrahydroxycalix<4>arene
• 英文别名: 5,17-Di-tert-butyl-11,23-dichloro-25,26,27,28-tetrahydroxycalix<4>arene；5,17-Di-tert-butyl-11,23-dichloro-25,26,27,28-tetrahydroxycalix[4]arene；5,17-Ditert-butyl-11,23-dichloropentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
• CAS: 127679-84-9；133908-48-2
• 化学式: C₃₆H₃₈Cl₂O₄
• 分子量: 605.601
• InChiKey: CVHVFRRQJPETBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  42
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-叔-丁基-2,6-二(羟基甲基)苯酚 在 硫酸 四氯化钛 作用下， 以 1,4-二氧六环 为溶剂， 反应 96.5h， 生成 11,23-Di-tert-butyl-5,17-dichloro-25,26,27,28-tetrahydroxycalix<4>arene
  参考文献：
  名称：

  A stepwise synthesis of functionalized calix [4]arenes and a calix[6]arene with alternate electron-withdrawing substituents

  摘要：

  DOI：

  10.1016/s0040-4020(01)85448-x

文献信息

• Preparation, stereochemistry, and reactions of the bis(spirodienone) derivatives of p-tert-butylcalix[4]arene
  作者：Ariel M. Litwak、Flavio Grynszpan、Oleg Aleksiuk、Shmuel Cohen、Silvio E. Biali

  DOI：10.1021/jo00054a023

  日期：1993.1

  The stereochemistry of the spirodienone derivatives of p-tert-butylcalix[4]arene (1) is analyzed. Treatment of 1 with base and 2 equiv of phenyltrimethylammonium tribromide resulted in the formation of a mixture of three main products (4A, 4A', and 4B) each containing two spirodienone moieties. The molecules slowly mutually interconvert in solution, and in toluene at 80-degrees-C the equilibrium mixture is composed of 10% 4A', 65% 4A, and 25% 4B. From the NMR data, it is concluded that both 4A and 4A' are systems in which the two cyclohexadienone groups are at distal positions (1,3) whereas 4B has C(s) symmetry and the cyclohexadienone rings are at proximal (1,2) positions. Unambiguous structural characterization of the systems was achieved by X-ray crystallography which indicates that 4A' is the chiral form (C2 symmetry) while 4A is the meso (C(i)) form. Attempted reduction of 4A resulted in the regeneration of 1. Reaction of 4A with HCl results in chloro-de-tert-butylation of two rings and rearomatization. Reaction of 4A, 4A', and 4B with excess benzyne yielded the corresponding Diels-Alder adducts 10A, 10A', and 10B which do not interconvert in solution. Based on the NMR data it is concluded that for each compound the additions to the two spirodienones occurred with identical diastereofacial discrimination. The Diels-Alder adducts are the first systems in which the phenolic oxygens of a calixarene were converted into nonconjugated ketone groups.
• Litwak Ariel M., Grynszpan Flavio, Aleksiuk Oleg, Cohen Shmuel, Biali Sil+, J. Org. Chem., 58 (1993) N 2, S 393-402
  作者：Litwak Ariel M., Grynszpan Flavio, Aleksiuk Oleg, Cohen Shmuel, Biali Sil+

  DOI：——

  日期：——
• A stepwise synthesis of functionalized calix [4]arenes and a calix[6]arene with alternate electron-withdrawing substituents
  作者：Javier de Mendoza、Pedro M. Nieto、Pilar Prados、Concha Sánchez

  DOI：10.1016/s0040-4020(01)85448-x

  日期：1990.1