Alternatived Products of [ 103-59-3 ]
Product Details of [ 103-59-3 ]
| CAS No. : | 103-59-3 |
MDL No. : | MFCD00048316 |
| Formula : |
C13H16O2
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | KLKQSZIWHVEARN-RMKNXTFCSA-N |
| M.W : | 204.26 |
Pubchem ID : | 5355851 |
| Synonyms : |
|
Application In Synthesis of [ 103-59-3 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 103-59-3 ]
- 1
-
[ 103-59-3 ]
-
[ 60533-01-9 ]
| Yield | Reaction Conditions | Operation in experiment |
| 17% |
Stage #1: cinnamyl isobutyrate With triethylamine at -60℃; for 0.0833333h; Inert atmosphere;
Stage #2: With trimethylsilyl trifluoromethanesulfonate at -60 - 20℃; for 24h; Inert atmosphere; |
Typical procedure for Ireland-Claisen rearrangement with Et3N as a base
General procedure: Ester 1 (2.34 mmol) was added into solution of Et3N (1.6 mL, 11.51 mmol) in dry CH2Cl2 (2.2 mL) under a nitrogen atmosphere. The reaction mixture was cooled to -60 °C. Then, trialkyl silyl triflate (3.7 mmol) was added dropwise. Next, an organocatalyst (10 mol %) was added in one portion. The reaction temperature was allowed to reach ambient temperature and the reaction mixture was stirred at this temperature for 24 h. After the reaction, the solvent was evaporated under reduced pressure. Diethyl ether (5 mL) and 1.3 M NaOH (7 mL) were added to the distillation residue. The aqueous layer was washed with CH2Cl2 (3x8 mL) and after that it was acidified with concentrated HCl. The products were extracted with CH2Cl2 (3x8 mL). The organic phase was washed with water (3x12 mL), dried with anhydrous MgSO4 and the solvent was evaporated under reduced pressure. |
|
With sodium hydride In toluene |
|
|
With hydrogenchloride; nitrobenzene; lithium diisopropyl amide Yield given. Multistep reaction; |
|
Reference：
[1]Krištofíková, Dominika; Filo, Juraj; Mečiarová, Mária; Šebesta, Radovan
[Beilstein Journal of Organic Chemistry, 2019, vol. 15, p. 2948 - 2957]
[2]Malzieu
[Bulletin de la Societe Chimique de France, 1976, vol. II, # 5-6, p. 879 - 882]
[3]Arnold, Richard T.; Kulenovic, Srdanka T.
[Journal of Organic Chemistry, 1980, vol. 45, # 5, p. 891 - 894]
- 2
-
[ 103-59-3 ]
-
[ 60532-99-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydride In toluene |
|
- 3
-
[ 104-54-1 ]
-
[ 79-30-1 ]
-
[ 103-59-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With pyridine In benzene |
|
- 4
-
[ 60533-00-8 ]
-
C26H30O4
[ No CAS ]
-
[ 103-59-3 ]
| Yield | Reaction Conditions | Operation in experiment |
| 1: 26%
2: 7% |
With indium(III) chloride; indium In acetonitrile Inert atmosphere; Sonication; |
|
Reference：
[1]Location in patent: scheme or table
Ishihara, Jun; Watanabe, Yuki; Koyama, Noriko; Nishino, Yukihiro; Takahashi, Keisuke; Hatakeyama, Susumi
[Tetrahedron, 2011, vol. 67, # 20, p. 3659 - 3667]
- 5
-
[ 104-54-1 ]
-
C26H30O4
[ No CAS ]
-
[ 103-59-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: pyridine; dmap / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
2: indium(III) chloride; indium / acetonitrile / Inert atmosphere; Sonication |
|
Reference：
[1]Ishihara, Jun; Watanabe, Yuki; Koyama, Noriko; Nishino, Yukihiro; Takahashi, Keisuke; Hatakeyama, Susumi
[Tetrahedron, 2011, vol. 67, # 20, p. 3659 - 3667]
- 6
-
[ 103-59-3 ]
-
[ 100-46-9 ]
-
C20H25NO2
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 12% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride; caesium carbonate In tetrahydrofuran at 90℃; for 24h; Inert atmosphere; Sealed tube; |
|
Reference：
[1]Kim, Seung Wook; Wurm, Thomas; Brito, Gilmar A.; Jung, Woo-Ok; Zbieg, Jason R.; Stivala, Craig E.; Krische, Michael J.
[Journal of the American Chemical Society, 2018, vol. 140, # 29, p. 9087 - 9090]
- 7
-
[ 104-54-1 ]
-
[ 97-62-1 ]
-
[ 103-59-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With recombinant acyltransferase from Mycobacterium smegmatis In aq. phosphate buffer at 25℃; for 24h; Green chemistry; Enzymatic reaction; |
|
Reference：
[1]Perdomo, Igor Chiarelli; Gianolio, Stefania; Pinto, Andrea; Romano, Diego; Contente, Martina Letizia; Paradisi, Francesca; Molinari, Francesco
[Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 23, p. 6517 - 6522]
- 8
-
[ 103-59-3 ]
-
3-phenyloxiran-2-yl methyl isobutyrate
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 88% |
With 3,5,5-trimethyl hexanal; aluminium oxide nanoparticles; oxygen In acetonitrile at 60℃; for 24h; Schlenk technique; |
B. General procedure for the preparation of epoxides 2
General procedure: To a 25 mL dried Schlenk tube was added the mixture of nano-Al2O3 (10.2 mg), alkene1 (1.0 mmol), 3, 5, 5-trimethylhexanal (3.0 mmol) in dry MeCN (5 mL) successively.The resulting mixture was stirred at 60 °C for 24 h under 1 atm of O2. After the reactionwas completed, the reaction mixture was cooled to room temperature, diluted withEtOAc (25 mL) and filtered. After removing the solvent under vacuum, the crudeproduct was separated by column chromatography on silica gel using PE-EtOAc aseluent to give the desired product 2. |
Reference：
[1]Zhou, Xuan; Wang, Qiong; Xiong, Wenfang; Wang, Lu; Ye, Rongkai; Xiang, Ge; Qi, Chaorong; Hu, Jianqiang
[Synlett, 2020, vol. 31, # 18, p. 1789 - 1794]
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