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CAS RN: 1883396-49-3 | Product Number: P2380
(S)-[4-(Pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine-2,6-diyl]bis[bis[4-(tert-butyl)phenyl]methanol]
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![(S)-[4-(Pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine-2,6-diyl]bis[bis[4-(tert-butyl)phenyl]methanol]](/_ui/responsive/theme-tci/images/missing_product_zoom.jpg "(S)-[4-(Pyridin-4-yl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine-2,6-diyl]bis[bis[4-(tert-butyl)phenyl]methanol]")
Purity: >85.0%(HPLC)
Synonyms:
Product Documents:
| Size | Unit Price | Saitama (Kawaguchi) | Hyogo (Amagasaki) | Stock in other WH |
Shipping Information
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|---|---|---|---|---|---|
| 50MG |
¥54,800
|
3 | It can be shipped from Saitama warehouse on the same day* | Contact Us |
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* The displayed price is the unit price and does not include consumption tax. The unit prices displayed are the latest and are subject to change without notice.
* To send your quote request for bulk quantities, please click on the "Request Bulk Quote" button. Please note that we cannot offer bulk quantities for some products.
*TCI frequently reviews storage conditions to optimize them. Please note that the latest information on the storage temperature for the products is described on our website.
| Product Number | P2380 |
| Purity / Analysis Method | >85.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__6__9H__7__2N__2O__2 = 961.35 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| CAS RN | 1883396-49-3 |
| PubChem Substance ID | 354333549 |
Specifications
| Appearance | Light orange to Yellow to Green powder to crystal |
| Purity(HPLC) | min. 85.0 area% |
| Elemental analysis(Nitrogen) | 2.50 to 3.30 % |
| Specific rotation [a]20/D | -270 to -310 deg(C=0.2, CHCl3) |
| NMR | confirm to structure |
Properties (reference)
| Specific Rotation | -290° (C=0.2,CHCl3) |
GHS
Related Laws:
Transport Information:
Application
A Highly Active 4-Dimethylaminopyridine (DMAP) Derivative Chiral Nucleophilic Catalyst
These asymmetric organocatalysts [P2380] and [P2617] are novel chiral DMAP derivatives, developed by Mandai and Suga et al.1) They show extremely high catalytic activity (0.1-0.5 mol % catalyst) and enantioselectivity in chiral acylating reactions, such as Steglich rearrangements1), the kinetic resolution of secondary carbinols2) and D,L-1,2-diols3), and the desymmetrization of meso-1,2-diols.4)
References
- 1)H. Mandai, K. Fujii, H. Yasuhara, K. Abe, K. Mitsudo, T. Korenaga, S. Suga, Nat. Commun. 2016, 7, 11297.
- 2)K. Fujii, K. Mitsudo, H. Mandai, S. Suga, Bull. Chem. Soc. Jpn. 2016, 89, 1081.
- 3)K. Fujii, K. Mitsudo, H. Mandai,, S. Suga, Adv. Synth. Catal. 2017, 359, 2778.
- 4)H. Mandai, H. Yasuhara, K. Fujii, Y. Shimomura, K. Mitsudo, S. Suga, J. Org. Chem. 2017, 82, 6846.
Application
Enantioselective Steglich Rearrangement with a Highly Active Chiral Nucleophilic Catalyst
Typical Procedure(Steglich rearrangement,1) R=CH3):
To a solution of phenyl 2-((phenoxycarbonyl)oxy)-3-methyl-1H-indole-1-carboxylate (37.4 mg, 0.1 mmol) in THF (0.25 mL) is added a solution of the DMAP chiral analog [P2380] (0.48 mg, 0.5 µmol) in THF at -20 °C. The reaction mixture was stirred for 5 h at -20 °C and then 1 M aqueous HCl is added. The resulting mixture is extracted with EtOAc, dried over MgSO4 and concentrated in vacuo. The purification of the crude product by flash column chromatography on a short pad of silica gel (eluent: hexane/Et2O = 1/1) gives (S)-diphenyl 3-methyl-2-oxoindoline-1,3-dicarboxylate (36.9 mg, 99% yield).
To a solution of phenyl 2-((phenoxycarbonyl)oxy)-3-methyl-1H-indole-1-carboxylate (37.4 mg, 0.1 mmol) in THF (0.25 mL) is added a solution of the DMAP chiral analog [P2380] (0.48 mg, 0.5 µmol) in THF at -20 °C. The reaction mixture was stirred for 5 h at -20 °C and then 1 M aqueous HCl is added. The resulting mixture is extracted with EtOAc, dried over MgSO4 and concentrated in vacuo. The purification of the crude product by flash column chromatography on a short pad of silica gel (eluent: hexane/Et2O = 1/1) gives (S)-diphenyl 3-methyl-2-oxoindoline-1,3-dicarboxylate (36.9 mg, 99% yield).
References
- 1)H. Mandai, K. Fujii, H. Yasuhara, K. Abe, K. Mitsudo, T. Korenaga, S. Suga, Nat. Commun. 2016, 7, 11297.
- 2)K. Fujii, K. Mitsudo, H. Mandai, S. Suga, Bull. Chem. Soc. Jpn. 2016, 89, 1081.
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