Alternatived Products of [ 1955-39-1 ]
Product Details of [ 1955-39-1 ]
CAS No. : | 1955-39-1 |
MDL No. : | MFCD00460031 |
Formula : |
C10H8O2
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
160.17
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 1955-39-1 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 1955-39-1 ]
* 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 [ 1955-39-1 ]
- 1
-
[ 1955-39-1 ]
-
[ 5814-37-9 ]
-
3-phenyl-7-<i>p</i>-tolyl-pyrano[4,3-<i>c</i>]pyran-1,5-dione
[ No CAS ]
-
(<i>E</i>)-5-phenyl-5'-<i>p</i>-tolyl-[3,3']bifurylidene-2,2'-dione
[ No CAS ]
- 2
-
[ 1955-39-1 ]
-
[ 124-40-3 ]
-
[ 26976-88-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
With diethyl ether |
|
- 3
-
[ 2051-95-8 ]
-
[ 1955-39-1 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With acetyl chloride; at 20℃; for 1h; |
To 3-benzoylpropionic acid (15 g, 0.084 mol), acetyl chloride (150 mL, 2.1 mol) was added and the mixture was stirred at room temperature for 1 h. The acetyl chloride excess was removed in vacuo. Recrystallization of the residue from diethyl ether afforded 5-phenylfuran-2(3H)-one, light yellow powder, m.p. 86-88 C (cf. Ref. 23: 88-89 C), yield 11.7 g (87%). 1H NMR (CDCl3), delta: 3.42 (d, 2 H, CH2, J = 2.3 Hz); 5.79 (m, 1 H, CH); 7.38-7.47 (m, 3 H, m-Ph, p-Ph); 7.58-7.63 (m, 2 H, o-Ph). |
43% |
With acetic anhydride; at 90℃; for 5h; |
[0095] The compound 10 was synthesized in accordance with the following scheme. [C00004] [00004] [0096] Namely, 1.80 g (10.1 mmol) of 3-benzoylpropionic acid (11) was heated at 90 C. for 5 hours in 10 ml of acetic anhydride. After removing the solvent, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 705 mg (43%) of a lactone body 12. |
Reference:
[1]Russian Chemical Bulletin,2015,vol. 64,p. 859 - 863
Izv. Akad. Nauk, Ser. Khim.,2015,p. 859 - 863,5
[2]Heterocycles,2006,vol. 68,p. 1121 - 1138
[3]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 1545 - 1548
[4]Russian Journal of Applied Chemistry,1996,vol. 69,p. 428 - 433
[5]Tetrahedron,1990,vol. 46,p. 3489 - 3502
[6]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1253 - 1254
[7]Chemical Communications,2015,vol. 51,p. 15835 - 15838
[8]Patent: US2004/236147,2004,A1 .Location in patent: Page 9-10
[9]Journal of Organometallic Chemistry,1987,vol. 327,p. 77 - 84
[10]Justus Liebigs Annalen der Chemie,1898,vol. 299,p. 18
[11]Justus Liebigs Annalen der Chemie,1898,vol. 299,p. 55
[12]Tetrahedron,1981,vol. 37,p. 2111 - 2114
[13]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 763 - 764
[14]Heterocyclic Communications,2006,vol. 12,p. 247 - 252
[15]Phosphorus, Sulfur and Silicon and the Related Elements,2006,vol. 181,p. 2037 - 2049
- 4
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[ 61550-02-5 ]
-
[ 1538-62-1 ]
-
[ 1955-39-1 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
In 1,2-dimethoxyethane; acetonitrile at 20℃; for 8h; |
|
- 5
-
[ 1955-39-1 ]
-
[ 101-16-6 ]
-
[ 1056199-51-9 ]
- 6
-
[ 1955-39-1 ]
-
[ 14204-27-4 ]
-
5-phenyl-3,3-bis(phenylthio)furan-2(3H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With triethylamine In dichloromethane at 20℃; for 18h; |
4.2. General procedure for the synthesis of α,α-bisthiofunctionalized butenolides 3
General procedure: To a test tube equipped with a magnetic stirring bar were sequentially added butenolides 1 (0.20 mmol), N-(arylsulfanyl)succinimides 2 (0.41 mmol), and Et3N (0.02 mmol) in DCM (2.0 mL).Then the mixture was stired for indicated time at room temperature. After completion of the reaction, as monitored by TLC, the solvent was removed under reduced pressure, and the residue was subjected to flash chromatography on silica gel (petroleum ether/ethyl acetate 30/1) to give the corresponding product 3. |
Reference:
[1]Zhao, Jian-Qiang; Luo, Shu-Wen; Zhang, Xiao-Mei; Xu, Xiao-Ying; Zhou, Ming-Qiang; Yuan, Wei-Cheng
[Tetrahedron, 2017, vol. 73, # 36, p. 5444 - 5450]
- 7
-
[ 541-59-3 ]
-
[ 1955-39-1 ]
-
C14H11NO4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
98% |
With pepsin In water at 50℃; for 48h; Green chemistry; Enzymatic reaction; diastereoselective reaction; |
4. General procedure for the pepsin-catalyzed vinylogous Michael addition
General procedure: A round bottom flask was charged with γ-substituted butenolide (0.2 mmol), maleimide (0.4 mmol), pepsin (19.5 kU) and deionized water (1.0 mL). The resulting mixture was stirred at 50 °C and was monitored by TLC. Upon completion of the reaction, the enzyme was filtered out, and ethyl acetate was added to wash the filter cake and tomake the product dissolved in the filtrate. The organic layer was separated with a separatory funnel, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography with petroleum ether/ethyl acetate (2:1-1:1) as eluent to afford the product. |
- 8
-
[ 128-53-0 ]
-
[ 1955-39-1 ]
-
C16H15NO4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
95% |
With pepsin; In water; at 50℃; for 48h;Green chemistry; Enzymatic reaction; |
General procedure: A round bottom flask was charged with gamma-substituted butenolide (0.2 mmol), maleimide (0.4 mmol), pepsin (19.5 kU) and deionized water (1.0 mL). The resulting mixture was stirred at 50 C and was monitored by TLC. Upon completion of the reaction, the enzyme was filtered out, and ethyl acetate was added to wash the filter cake and tomake the product dissolved in the filtrate. The organic layer was separated with a separatory funnel, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography with petroleum ether/ethyl acetate (2:1-1:1) as eluent to afford the product. |
- 9
-
[ 1955-39-1 ]
-
[ 4144-22-3 ]
-
C18H19NO4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
64% |
With pepsin; In water; at 50℃; for 48h;Green chemistry; Enzymatic reaction; |
General procedure: A round bottom flask was charged with gamma-substituted butenolide (0.2 mmol), maleimide (0.4 mmol), pepsin (19.5 kU) and deionized water (1.0 mL). The resulting mixture was stirred at 50 C and was monitored by TLC. Upon completion of the reaction, the enzyme was filtered out, and ethyl acetate was added to wash the filter cake and tomake the product dissolved in the filtrate. The organic layer was separated with a separatory funnel, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography with petroleum ether/ethyl acetate (2:1-1:1) as eluent to afford the product. |