Design of Macrocyclic Multidentates Discriminating Molecular Chirality and Their Recognition Abilities
| Project/Area Number |
13650903
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Osaka University |
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Principal Investigator |
NAKATSUJI Yohji Osaka University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (00127268)
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| Co-Investigator(Kenkyū-buntansha) |
KIDA Toshiyuki Osaka University, Graduate School of Engineering, Assistant Professor, 大学院・工学研究科, 助手 (20234297)
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| Project Period (FY) |
2001 – 2002
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| Project Status |
Completed (Fiscal Year 2002)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2002: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2001: ¥2,700,000 (Direct Cost: ¥2,700,000)
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| Keywords | Molecular Recognition / Chiral Crown Ether / Complexation / クラウンエーテル / キラル認識 / リパーゼ触媒反応 / C_2-対称 |
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| Research Abstract |
In this study, we developed a convenient synthetic procedure for C_2-symmetirc chiral crown ether having reactive hydroxyl groups and examined the chiral discrimination ability of the several C_2-symmetirc crown ether derivatives derived from the key intermediate toward primary ammonium salts. The results are summarized as follows.
1. As a preparative study for the development of chiral recognition host molecules based on the crown ether scaffold, the participation of the sidearm in the complexation with guest cations was examined by using several type of double armed lariat ethers. As a result, the introduction of the electron-donating sidearm to the crown ring was found to be highly effective in increasing the complexation ability toward alkali metal and alkaline earth metal cations.
2. A new convenient synthetic procedure for (S, S)-2, 12-bis(hydroxymethyl)-2, 12-dimethyl-18-crown-6 possessing plural reactive functional groups was developed.
3. Several types of sidearms such as naphthyloxymethyl, phenyloxymethyl, benzyloxymethyl, allyloxymethyl, and acectyloxymethyl were introduced to the 18 crown-6 ring by modification of the hydroxyl groups of (R, R)-2, 12 bis(hydroxymemyl)-2, 12-dimethyl-18-crown-6. The chiral recognition ability of the resulting crown ether derivatives toward (R) and (S) of the perchlorate salts of α-(1-naphtyl) ethylamine, α-phenylethylamine, and phenylglycinol was estimated by 1H-NMR titration method and the positive participation of the sidearm in the chiral recognition was observed.
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Report
(3 results)
Research Products
(6 results)
