Alternatived Products of [ 35340-49-9 ]
Product Details of [ 35340-49-9 ]
CAS No. : | 35340-49-9 |
MDL No. : | MFCD00005056 |
Formula : |
C24H18O7
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | YKSJJXGQHSESKB-UHFFFAOYSA-N |
M.W : |
418.40
|
Pubchem ID : | 629056 |
Synonyms : |
|
Application In Synthesis of [ 35340-49-9 ]
* 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 [ 35340-49-9 ]
- 1
-
[ 518-44-5 ]
-
[ 108-24-7 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
In pyridine Ambient temperature; |
|
|
With pyridine Ambient temperature; Yield given; |
|
Reference:
[1]Sharma, Padam N.; Brossi, Arnold
[Helvetica Chimica Acta, 1984, vol. <1> 67, # 35, p. 301 - 304]
[2]Tadic, Dragana; Brossi, Arnold
[Heterocycles, 1990, vol. 31, # 11, p. 1975 - 1982]
- 2
-
[ 54-04-6 ]
-
[ 35340-49-9 ]
-
diacetyldihydrofluorescein amide of mescaline
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
28% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; |
|
- 3
-
[ 3476-50-4 ]
-
[ 35340-49-9 ]
-
[ 89759-27-3 ]
Yield | Reaction Conditions | Operation in experiment |
65% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; with other alkohols and amines, also with codein, quinin, mescalin; |
|
65% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; |
|
Reference:
[1]Sharma, Padam N.; Brossi, Arnold
[Helvetica Chimica Acta, 1984, vol. <1> 67, # 35, p. 301 - 304]
[2]Sharma, Padam N.; Brossi, Arnold
[Helvetica Chimica Acta, 1984, vol. <1> 67, # 35, p. 301 - 304]
- 4
-
[ 35340-49-9 ]
-
[ 74515-40-5 ]
-
[ 89759-28-4 ]
Yield | Reaction Conditions | Operation in experiment |
77% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; |
|
- 5
-
[ 35340-49-9 ]
-
α-deoxydihydroartemisinin
[ No CAS ]
-
C39H40O10
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; |
|
- 6
-
[ 35340-49-9 ]
-
(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol
[ No CAS ]
-
diacetyldihydrofluorescyl dihydroqinghaosu
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
69.4% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature; |
|
- 7
-
[ 35340-49-9 ]
-
quinine
[ No CAS ]
-
diacetyldihydrofluorescein ester of quinine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
46% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; |
|
- 8
-
[ 35340-49-9 ]
-
codein
[ No CAS ]
-
diacetyldihydrofluorescein ester of codeine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
38% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature; |
|
- 10
-
[ 108-24-7 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium acetate |
|
- 11
-
[ 35340-49-9 ]
-
[ 518-44-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Alkaline hydrolysis; |
|
|
With methanol; sodium hydroxide |
|
Reference:
[1]Saengkhae, Chantarawan; Loetchutinat, Chatchanok; Garnier-Suillerot, Arlette
[Biochemical Pharmacology, 2003, vol. 65, # 6, p. 969 - 977]
[2]Le, Hoa Thi; Nguyen, Dinh Phi Long; Shin, Hyo Seob; Jung, Woong; Kang, Chulhun; Kim, Tae Woo
[Free Radical Research, 2021, vol. 55, # 4, p. 461 - 468]
- 12
-
[ 35340-49-9 ]
-
[ 518-39-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 77 percent / DCC, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
2: 29 percent / 1.) NH3 vapor, 2.) iodine vapor / 1.) 15 min, 2.) 15 min
3: 2N NaOH / methanol / 2 h / Ambient temperature |
|
- 13
-
[ 35340-49-9 ]
-
[ 89759-30-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 77 percent / DCC, 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / Ambient temperature
2: 29 percent / 1.) NH3 vapor, 2.) iodine vapor / 1.) 15 min, 2.) 15 min |
|
- 14
-
fluorescein
[ No CAS ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 3.4 g / Zn / ethanol / Heating
2: 94 percent / pyridine / Ambient temperature |
|
- 15
-
[ 97744-44-0 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: H2 / Pd(OH)2/C / ethanol / 0.5 h / Ambient temperature
2: pyridine / Ambient temperature |
|
- 16
-
[ 518-45-6 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 81 percent / K2CO3 / dimethylformamide / 24 h / 80 °C
2: H2 / Pd(OH)2/C / ethanol / 0.5 h / Ambient temperature
3: pyridine / Ambient temperature |
|
- 17
-
[ 596-09-8 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 18h; |
2.1.2 2.1.2 Synthesis of compound M-4
Compound M-3 (153 mg, 0.367 mmol) was dissolved in 15 mL of ethyl acetate, 10% palladium/carbon (15 mg) was added, hydrogen was passed through, the reaction was carried out at room temperature for 18 h, suction filtered, and the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (DCM:MeOH, 30:1 v/v) to give 130 mg of white solid in 85% yield. |
74% |
With glacial acetic acid; zinc In tetrahydrofuran at 85℃; for 0.25h; Microwave irradiation; |
Flu-ester
General procedure: To a solution of 2 (50 mg, 0.14 mmol) in THF (2 mL) and acetic acid (0.2 mL) was added Zn powder (50 mg). The reaction mixture was irradiated at 30 W and 85 °C in microwave reactor (CEM Discover, Dynamic mode, cooling air) for 15 min. The reaction mixture was filtered and the filter cake was washed with THF (10 mL 3). The filtrate was concentrated and purified by column chromatography (hexane:ethyl acetate = 2:1, v/v) to yield the desired product (35.8 mg, 0.10 mmol, yield 71%). |
|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 18h; |
|
|
With glacial acetic acid; zinc Microwave irradiation; |
|
Reference:
[1]Current Patent Assignee: QUZHOU MEDICAL UNIV - CN114394978, 2022, A
Location in patent: Paragraph 0077-0079
[2]Le, Hoa Thi; Jo, Hye-Ryeong; Oh, Se-Yun; Jung, Jinwook; Kim, Young Gi; Kang, Chulhun; Kim, Tae Woo
[Bulletin of the Korean Chemical Society, 2021, vol. 42, # 2, p. 279 - 285]
[3]Kitley, Weston R.; Santa Maria, Peter J.; Cloyd, Ryan A.; Wysocki, Laura M.
[Chemical Communications, 2015, vol. 51, # 40, p. 8520 - 8523]
[4]Le, Hoa Thi; Nguyen, Dinh Phi Long; Shin, Hyo Seob; Jung, Woong; Kang, Chulhun; Kim, Tae Woo
[Free Radical Research, 2021, vol. 55, # 4, p. 461 - 468]
- 18
-
[ 35340-49-9 ]
-
C29H24O7
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness |
|
- 19
-
[ 35340-49-9 ]
-
C35H32O7
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness
3: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness |
|
- 20
-
[ 35340-49-9 ]
-
[ 855751-82-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: ammonium bicarbonate / tetrahydrofuran; methanol; water / 60 h / 20 °C / Inert atmosphere; Darkness
3: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness
4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 18 h / 20 °C / Inert atmosphere; Darkness |
|
- 21
-
[ 7314-44-5 ]
-
[ 35340-49-9 ]
-
C33H28O9
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
207.3 mg |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere; |
|
- 22
-
[ 35340-49-9 ]
-
[ 146651-75-4 ]
-
C31H28N2O6
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
90% |
Stage #1: dihydrofluorescein diacetate With thionyl chloride Inert atmosphere;
Stage #2: tert–butyl (2–aminophenyl)carbamate With triethylamine In acetonitrile at 20℃; for 1h;
Stage #3: With lithium hydroxide In tetrahydrofuran; water at 20℃; for 4h; |
|
Reference:
[1]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
- 23
-
[ 35340-49-9 ]
-
C40H28N2O5S2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: thionyl chloride / Inert atmosphere
1.2: 1 h / 20 °C
1.3: 4 h / 20 °C
2.1: borane solution / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
2.2: 2 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 20 °C
4.1: hydrogenchloride / dichloromethane / 1 h / 20 °C
4.2: 1 h / 0 - 20 °C |
|
Reference:
[1]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
- 24
-
[ 35340-49-9 ]
-
C26H17N3O3
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: thionyl chloride / Inert atmosphere
1.2: 1 h / 20 °C
1.3: 4 h / 20 °C
2.1: borane solution / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
2.2: 2 h / 20 °C
3.1: hydrogenchloride / tetrahydrofuran / 1 h / 20 °C
3.2: 3 h / 0 - 20 °C |
|
|
Multi-step reaction with 5 steps
1.1: thionyl chloride / Inert atmosphere
1.2: 1 h / 20 °C
1.3: 4 h / 20 °C
2.1: borane solution / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
2.2: 2 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 20 °C
4.1: hydrogenchloride / dichloromethane / 1 h / 20 °C
4.2: 1 h / 0 - 20 °C
5.1: S-Nitrosoglutathione; sodium sulfide / tetrahydrofuran; aq. phosphate buffer / 0.5 h / pH 7.4 / Darkness; Inert atmosphere |
|
Reference:
[1]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
[2]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
- 25
-
[ 35340-49-9 ]
-
C31H28N2O5
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: dichlorosulfoxide / Inert atmosphere
1.2: 1 h / 20 °C
1.3: 4 h / 20 °C
2.1: borane solution / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
2.2: 2 h / 20 °C |
|
|
Multi-step reaction with 4 steps
1.1: dichlorosulfoxide / 12 h / Reflux; Inert atmosphere
2.1: triethylamine / acetonitrile / 3.5 h / 0 - 20 °C / Reflux; Inert atmosphere
3.1: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 20 °C
4.1: borane-THF / tetrahydrofuran / 4 h / Reflux; Inert atmosphere
4.2: 2 h / 20 °C |
|
Reference:
[1]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
[2]Current Patent Assignee: QUZHOU MEDICAL UNIV - CN114394978, 2022, A
- 26
-
[ 35340-49-9 ]
-
C55H42N4O7S4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: thionyl chloride / Inert atmosphere
1.2: 1 h / 20 °C
1.3: 4 h / 20 °C
2.1: borane solution / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
2.2: 2 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 3 h / 20 °C |
|
Reference:
[1]Chen, Wei; Matsunaga, Tetsuro; Neill, Deshka L.; Yang, Chun-tao; Akaike, Takaaki; Xian, Ming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16067 - 16070][Angew. Chem., 2019, vol. 131, # 45, p. 16213 - 16216,4]
- 27
-
[ 2321-07-5 ]
-
[ 35340-49-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: pyridine
2: glacial acetic acid; zinc / tetrahydrofuran / 0.25 h / 85 °C / Microwave irradiation |
|
|
Multi-step reaction with 2 steps
1: pyridine
2: glacial acetic acid; zinc / Microwave irradiation |
|
|
Multi-step reaction with 2 steps
1: Reflux
2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h / 20 °C |
|
Reference:
[1]Le, Hoa Thi; Jo, Hye-Ryeong; Oh, Se-Yun; Jung, Jinwook; Kim, Young Gi; Kang, Chulhun; Kim, Tae Woo
[Bulletin of the Korean Chemical Society, 2021, vol. 42, # 2, p. 279 - 285]
[2]Le, Hoa Thi; Nguyen, Dinh Phi Long; Shin, Hyo Seob; Jung, Woong; Kang, Chulhun; Kim, Tae Woo
[Free Radical Research, 2021, vol. 55, # 4, p. 461 - 468]
[3]Current Patent Assignee: QUZHOU MEDICAL UNIV - CN114394978, 2022, A
- 28
-
[ 35340-49-9 ]
-
[ 74-89-5 ]
-
C25H21NO6
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: dihydrofluorescein diacetate With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran
Stage #2: methylamine In tetrahydrofuran |
|
Reference:
[1]Le, Hoa Thi; Nguyen, Dinh Phi Long; Shin, Hyo Seob; Jung, Woong; Kang, Chulhun; Kim, Tae Woo
[Free Radical Research, 2021, vol. 55, # 4, p. 461 - 468]
- 29
-
[ 35340-49-9 ]
-
C40H30N4O7
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1.1: dichlorosulfoxide / 12 h / Reflux; Inert atmosphere
2.1: triethylamine / acetonitrile / 3.5 h / 0 - 20 °C / Reflux; Inert atmosphere
3.1: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 20 °C
4.1: borane-THF / tetrahydrofuran / 4 h / Reflux; Inert atmosphere
4.2: 2 h / 20 °C
5.1: N,N-dimethyl-formamide / 0.25 h / Inert atmosphere
5.2: 6 h / 20 °C / Inert atmosphere
6.1: hydrogenchloride / dichloromethane; lithium hydroxide monohydrate / 2 h / 20 °C |
|
- 30
-
[ 35340-49-9 ]
-
C45H38N4O9
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: dichlorosulfoxide / 12 h / Reflux; Inert atmosphere
2.1: triethylamine / acetonitrile / 3.5 h / 0 - 20 °C / Reflux; Inert atmosphere
3.1: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 20 °C
4.1: borane-THF / tetrahydrofuran / 4 h / Reflux; Inert atmosphere
4.2: 2 h / 20 °C
5.1: N,N-dimethyl-formamide / 0.25 h / Inert atmosphere
5.2: 6 h / 20 °C / Inert atmosphere |
|
- 31
-
[ 35340-49-9 ]
-
C31H28N2O6
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: dichlorosulfoxide / 12 h / Reflux; Inert atmosphere
2: triethylamine / acetonitrile / 3.5 h / 0 - 20 °C / Reflux; Inert atmosphere
3: lithium hydroxide monohydrate; lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 20 °C |
|
- 32
-
[ 35340-49-9 ]
-
C35H32N2O8
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: dichlorosulfoxide / 12 h / Reflux; Inert atmosphere
2: triethylamine / acetonitrile / 3.5 h / 0 - 20 °C / Reflux; Inert atmosphere |
|
- 33
-
[ 35340-49-9 ]
-
C24H17ClO6
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With dichlorosulfoxide for 12h; Reflux; Inert atmosphere; |
2.1.3 2.1.3 Synthesis of compound M-5
Compound M-4 (418 mg, 1 mmol) was dissolved in SOCl2 (3 mL), and the reaction was refluxed for 2 h under nitrogen protection. After the reaction was completed, it was cooled to room temperature, and SOCl2 was removed under reduced pressure. The concentrated residue was dissolved in anhydrous CH3CN (20 mL), and added to a mixed solution of Et3N (405 mg, 4 mmol) and N-Boc-1,2-phenylenediamine (140 mg, 0.67 mmol). The resulting mixture was reacted at 0°C for 0.5 h and then at room temperature for 3 h. Water (100 mL) was added to the above reaction solution to quench the reaction and extracted with ethyl acetate (3 x 30 mL). The organic phase was dried with anhydrous Na2SO4,Concentrate under reduced pressure. |