| Project/Area Number |
10470467
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (B).
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | KYOTO UNIVERSITY |
|---|
Principal Investigator |
FUJI Kaoru Inst. for Chem. Res., Kyoto Univ. Professor, 化学研究所, 教授 (20027056)
|
|---|
| Co-Investigator(Kenkyū-buntansha) |
TANAKA Kiyoshi Univ. of Shizuoka, Professor, 薬学部, 教授 (50093266)
|
|---|
| Project Period (FY) |
1998 – 2000
|
| Project Status |
Completed (Fiscal Year 2000)
|
| Budget Amount *help |
¥12,200,000 (Direct Cost: ¥12,200,000)
Fiscal Year 2000: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1998: ¥6,000,000 (Direct Cost: ¥6,000,000)
|
|---|
| Keywords | Atropisomer / Molecular recognition / Spirobenzopyran / Binaphthol / Photochromic Compound / フォトクロミック化合物 / 1,1′-binaphthalene-2,2′-diol / フェノールフタレイン / クラウンエーテル / 発色 / アミノ酸 / 不斉分子認識 / ビナフチルエーテル |
|---|
| Research Abstract |
The compounds with atropisomerism, such as 1,1'-binaphthyl derivatives, provide an effective asymmetric environment. Symmetric carbons have no flexibility at their chiral center. On the other hand, chiral environment of 1,1'-binaphthyl derivatives is flexible enough to relieve or adjust the steric interaction by changing the dihedral angle between two aromatic planes without changing the sense of chirality. Therefore, 1,1'-binaphthalene-2,2'-diol (BINOL) has been extensively utilized as a chiral controller for asymmetric syntheses and chiral recognition. A purpose of this research is to design the new atropisomeric compounds with the naphthalene rings and to utilize these compounds for the asymmetric molecular recognition.
This project includes two researches, namely synthesis of spirobenzopyran derivatives having optically active BINOL as a structural unit and creation a new type of atropisomerism. Spirobenzopyrans are known photochromic compounds that isomerize to their corresponding merocyanine forms under UV light, and vice versa under visible light or heat. One of the compounds we synthesized could discriminate the optical isomer of amino acids by the time of developing the color by the merocyanine form.
The atropisomers such as BINOL are due to a restricted rotation of a single bond. Our goal of this research was to synthesize new atropisomers through two single bonds. We have synthesized a number of 1,1'-binaphthyl ethers substituted at 8-and 8'-positions and shown that they could exist as a stable optical isomer when the substituents were bulky. These compounds are regarded as the simplest molecular bevel gear possessing only two cogs on each wheel, the gear slippage of which results in racemization.
|
