Synthesis and chiroptical properties of cylindrical macrocycles comprising two calix[3]aramide moieties

被引：14

作者：

Saito, Yuuki ^{[1
]}

Satake, Misa ^{[1
]}

Mon, Ryuichi ^{[1
]}

Okayasu, Misaki ^{[1
]}

Masu, Hyuma ^{[2
]}

Tominaga, Masahide ^{[3
]}

Katagiri, Kosuke ^{[4
]}

Yamaguchi, Kentaro ^{[3
]}

Kikkawa, Shoko ^{[1
]}

Hikawa, Hidemasa ^{[1
]}

Azumaya, Isao ^{[1
]}

机构：

[1] Toho Univ, Fac Pharmaceut Sci, 2-2-1 Miyama, Funahashi, Chiba 2748510, Japan

[2] Chiba Univ, Ctr Analyt Instrumentat, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan

[3] Tokushima Bunri Univ, Fac Pharmaceut Sci, Kagawa Campus,1314-1 Shido, Sanuki, Kagawa 7692193, Japan

[4] Konan Univ, Dept Chem, Fac Sci & Engn, Higashinada Ku, 8-9-1 Okamoto, Kobe, Hyogo 6588501, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 02期

关键词：

CYCLIC TRIAMIDES; DRUG DISCOVERY; CHIRALITY; CRYPTOPHANES; PRINCIPLES; DENDRIMERS; CRYSTAL; CAVITY; CAGE;

D O I：

10.1039/c9ob02022e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Calix[3]aramide-based cylindrical macrocycles were synthesized by the one-step amide coupling reaction of a monomer containing two meta-alkylaminobenzoic acid units linked by para-phenylene bridges. The major products included a meso-form and an enantiomeric pair, with stereochemistry derived from the direction of the amide bonds and their fixed conformation. Mirror-image ECD, VCD, and CPL spectra were observed in the enantiomeric pair and the absolute structure was determined by comparing measured and calculated ECD and VCD spectra.

引用

页码：230 / 236

页数：7

共 62 条

[1] An Enantiomerically Pure Alleno-Acetylenic Macrocycle: Synthesis and Rationalization of Its Outstanding Chiroptical Response [J].