Alternatived Products of [ 52959-28-1 ]
Product Details of [ 52959-28-1 ]
CAS No. : | 52959-28-1 |
MDL No. : | MFCD20133532 |
Formula : |
C10H10O6
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | CMTOZSKJCALTLF-UHFFFAOYSA-N |
M.W : |
226.18
|
Pubchem ID : | 14927440 |
Synonyms : |
|
Application In Synthesis of [ 52959-28-1 ]
* 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 [ 52959-28-1 ]
- 1
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[ 186581-53-3 ]
-
[ 19829-74-4 ]
-
[ 52959-28-1 ]
- 2
-
[ 67-56-1 ]
-
[ 19829-74-4 ]
-
[ 52959-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
67% |
With thionyl chloride; at 0℃;Reflux; |
To a solution of 15 (700.0 mg, 3.36 mmol) in MeOH (18 ml), SOCI2(1 .63 g, 1 .22 ml, 13.43 mmol, 4.0 eq) was added dropwise at 0 C. When the addition was completed the reaction mixture was refluxed overnight. The resulting suspension was cooled down to 0 C and then filtered, washing with cold methanol, to obtain 16 as white crystals (506.2 mg, 2.24 mmol, 67 % yield).1H and13C NMR in agreement with literature reference [Eur. J. Org. Chem. 2013, 36, 8135-8144]. |
|
With sulfuric acid; for 48h;Reflux; |
A solution of acid (3.18 g) and concentrated H2SO4 (4 mL) in methanol (64 mL) was heated under reflux for 2 days. The product was obtained upon cooling and was filtered off and washed with a small amount of MeOH to give pure methyl ester. |
|
With sulfuric acid; |
FIG. 5A shows the synthesis of 2,4-dihydroxy-5-nitrobenzoic acid from the commercially available 2,4-dihydroxybenzoic acid. The acid is then esterified and alkylated in high yields. The alkylation reaction is quite general, since methyl, ally, iso-butyl, octyl, and decyl bromides all have resulted in corresponding products with high yields (>95percent). |
Reference:
[1]Chemical Communications,2012,vol. 48,p. 2228 - 2230
[2]Journal of the American Chemical Society,2000,vol. 122,p. 2635 - 2644
[3]European Journal of Organic Chemistry,2013,p. 8135 - 8144
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 11117 - 11121
Angew. Chem.,2016,vol. 127,p. 11269 - 11273,5
[5]Patent: WO2018/130713,2018,A1 .Location in patent: Page/Page column 50
[6]Journal of the Chemical Society,1957,p. 1833,1834
[7]Journal of Organic Chemistry,2005,vol. 70,p. 10660 - 10669
[8]Patent: US9155738,2015,B2 .Location in patent: Page/Page column 358
[9]Patent: CN109305926,2019,A .Location in patent: Paragraph 0048
[10]Patent: WO2019/99922,2019,A1 .Location in patent: Paragraph 0035; 0129
- 3
-
[ 19829-74-4 ]
-
[ 77-78-1 ]
-
[ 52959-28-1 ]
- 4
-
[ 52959-28-1 ]
-
C21H35ClN2
[ No CAS ]
-
4,6-Bis-[N'-(4-dodecyl-phenyl)-N,N-dimethyl-carbamimidoyloxy]-isophthalic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With sodium hydride In tetrahydrofuran |
|
- 5
-
[ 108-46-3 ]
-
[ 52959-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 4 h / 200 °C / Schlenk technique
2: sulfuric acid / 15 h / Reflux |
|
|
Multi-step reaction with 2 steps
1: 4 h / 200 °C / Inert atmosphere
2: 6 h / Acidic conditions; Reflux; Inert atmosphere |
|
Reference:
[1]Marsh, Andrew; Nolen, Ernest G.; Gardinier, Kevin M.; Lehn, Jean-Marie
[Tetrahedron Letters, 1994, vol. 35, # 3, p. 397 - 400]
[2]Montarnal, Damien; Delbosc, Nicolas; Chamignon, Cécile; Virolleaud, Marie-Alice; Luo, Yingdong; Hawker, Craig J.; Drockenmuller, Eric; Bernard, Julien
[Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11117 - 11121][Angew. Chem., 2016, vol. 127, # 38, p. 11269 - 11273]
[3]Aksimentiev, Aleksei; Chen, Feng; Joshi, Himanshu; Roy, Arundhati; Shen, Jie; Ye, Ruijuan; Zeng, Huaqiang
[Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4806 - 4813][Angew. Chem., 2020, vol. 132, # 12, p. 4836 - 4843,8]
- 6
-
[ 52959-28-1 ]
-
[ 77-78-1 ]
-
[ 14965-05-0 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With potassium carbonate In acetone for 72h; Heating; |
|
|
With potassium carbonate In acetone |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[2]Madeja-Kotkowska,Z.
[Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1974, vol. 22, p. 365 - 375]
- 7
-
[ 6946-10-7 ]
-
[ 922-67-8 ]
-
[ 52959-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
18% |
With sodium hydride In tetrahydrofuran at -10℃; for 2h; |
|
- 8
-
[ 111-83-1 ]
-
[ 52959-28-1 ]
-
[ 267897-57-4 ]
Yield | Reaction Conditions | Operation in experiment |
99% |
With potassium carbonate In methanol; N,N-dimethyl-formamide at 100℃; for 16h; |
|
88% |
With potassium carbonate In N,N-dimethyl-formamide for 48h; Heating; |
|
88% |
With potassium carbonate In methanol; N,N-dimethyl-formamide at 100℃; for 48h; |
|
88% |
With potassium carbonate In methanol; N,N-dimethyl-formamide at 100℃; for 48h; |
|
|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; |
|
Reference:
[1]Montarnal, Damien; Delbosc, Nicolas; Chamignon, Cécile; Virolleaud, Marie-Alice; Luo, Yingdong; Hawker, Craig J.; Drockenmuller, Eric; Bernard, Julien
[Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11117 - 11121][Angew. Chem., 2016, vol. 127, # 38, p. 11269 - 11273]
[2]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[3]Zeng, Huaqiang; Miller, Rebecca S.; Flowers II, Robert A.; Gong, Bing
[Journal of the American Chemical Society, 2000, vol. 122, # 11, p. 2635 - 2644]
[4]Zeng; Ickes; Flowers II; Gong
[Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3574 - 3583]
[5]Aksimentiev, Aleksei; Chen, Feng; Joshi, Himanshu; Roy, Arundhati; Shen, Jie; Ye, Ruijuan; Zeng, Huaqiang
[Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4806 - 4813][Angew. Chem., 2020, vol. 132, # 12, p. 4836 - 4843,8]
- 9
-
[ 78-77-3 ]
-
[ 52959-28-1 ]
-
[ 231954-15-7 ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With potassium carbonate In N,N-dimethyl-formamide for 48h; Heating; |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 10
-
toluene-4-sulfonic acid 2-(3-methylbutoxy)propyl ester
[ No CAS ]
-
[ 52959-28-1 ]
-
4,6-bis[2-(3-methylbutoxy)propoxy]isophthalic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
54.5% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 48h; |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 11
-
[ 52959-28-1 ]
-
[ 62921-74-8 ]
-
[ 874210-29-4 ]
Yield | Reaction Conditions | Operation in experiment |
85.4% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 48h; |
|
70% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[2]Li, Minfeng; Yamato, Kazuhiro; Ferguson, Joseph S.; Gong, Bing
[Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12628 - 12629]
- 12
-
[ 52959-28-1 ]
-
[ 83948-53-2 ]
-
[ 874210-32-9 ]
Yield | Reaction Conditions | Operation in experiment |
86.6% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 36h; |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 13
-
[ 52959-28-1 ]
-
[ 110661-91-1 ]
-
[ 874210-33-0 ]
Yield | Reaction Conditions | Operation in experiment |
85.1% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 48h; Heating; |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 14
-
[ 358-23-6 ]
-
[ 52959-28-1 ]
-
[ 890705-76-7 ]
Yield | Reaction Conditions | Operation in experiment |
79% |
With pyridine In dichloromethane at 20℃; for 0.666667h; |
|
- 15
-
[ 52959-28-1 ]
-
[ 26690-80-2 ]
-
[ 898809-04-6 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 48h; |
|
Reference:
[1]Choi, Sungwook; Clements, Dylan J.; Pophristic, Vojislava; Ivanov, Ivaylo; Vemparala, Satyavani; Bennett, Joel S.; Klein, Michael L.; Winkler, Jeffrey D.; DeGrado, William F.
[Angewandte Chemie - International Edition, 2005, vol. 44, # 41, p. 6685 - 6689]
- 16
-
[ 915184-71-3 ]
-
[ 52959-28-1 ]
-
dimethyl 4,6-bis(2-(isopentyloxy)ethoxy)isophthalate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
60% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; |
|
|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 72h; |
|
Reference:
[1]Wei, Xiaoxi; Zhang, Guoqing; Shen, Yi; Zhong, Yulong; Liu, Rui; Yang, Na; Al-Mkhaizim, Fayez Y.; Kline, Mark A.; He, Lan; Li, Minfeng; Lu, Zhong-Lin; Shao, Zhifeng; Gong, Bing
[Journal of the American Chemical Society, 2016, vol. 138, # 8, p. 2749 - 2754]
[2]Zhang, Aimin; Ferguson, Joseph S.; Yamato, Kazuhiro; Zheng, Chong; Gong, Bing
[Organic Letters, 2006, vol. 8, # 22, p. 5117 - 5120]
- 17
-
[ 52959-28-1 ]
-
[ 109-73-9 ]
-
N,N'-dibutyl-4,6-dihydroxy-isophthalamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
22% |
In N,N-dimethyl-formamide at 110℃; for 48h; |
|
Reference:
[1]Santacroce, Paul V.; Davis, Jeffery T.; Light, Mark E.; Gale, Philip A.; Iglesias-Sanchez, Jose Carlos; Prados, Pilar; Quesada, Roberto
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1886 - 1887]
- 18
-
[ 52959-28-1 ]
-
[ 54176-27-1 ]
-
[ 939374-70-6 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With potassium carbonate In acetone for 36h; Heating; |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 19
-
[ 52959-28-1 ]
-
[ 874210-38-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: 3.5 g / NaOH / methanol; H2O / 20 °C |
|
|
Multi-step reaction with 2 steps
1: 85.4 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.9 percent / NaOH / H2O; methanol / 20 °C |
|
Reference:
[1]Li, Minfeng; Yamato, Kazuhiro; Ferguson, Joseph S.; Gong, Bing
[Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12628 - 12629]
[2]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 20
-
[ 52959-28-1 ]
-
[ 936347-09-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C |
|
- 21
-
[ 52959-28-1 ]
-
C26H40N2O14
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol; H2O / 20 °C |
|
- 22
-
[ 52959-28-1 ]
-
[ 936352-81-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol; H2O / 20 °C
5: 1.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C |
|
- 23
-
[ 52959-28-1 ]
-
C54H78N4O24
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol; H2O / 20 °C
5: 1.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
6: NaOH / methanol; H2O / 20 °C |
|
- 24
-
[ 52959-28-1 ]
-
[ 936354-31-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol; H2O / 20 °C
5: 1.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C |
|
- 25
-
[ 52959-28-1 ]
-
C54H80N6O22*2C2HF3O2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C
3: 0.95 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol; H2O / 20 °C
5: 1.3 g / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
6: TFA / CH2Cl2 / 20 °C |
|
- 26
-
[ 52959-28-1 ]
-
C44H55NO11S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: 3.5 g / NaOH / methanol; H2O / 20 °C
3: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C |
|
- 27
-
[ 52959-28-1 ]
-
[ 936354-38-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: 3.5 g / NaOH / methanol; H2O / 20 °C
3: 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide; N-hydroxybenzotriazole / CH2Cl2 / 20 h / 0 - 20 °C
4: NaOH / methanol |
|
- 28
-
[ 52959-28-1 ]
-
[ 492465-50-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 70 percent / K2CO3 / dimethylformamide / 80 °C
2: NaOH / methanol; H2O / 20 °C |
|
|
Multi-step reaction with 2 steps
1: 85.4 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 91 percent / KOH / H2O / 3 h / 80 °C |
|
Reference:
[1]Li, Minfeng; Yamato, Kazuhiro; Ferguson, Joseph S.; Gong, Bing
[Journal of the American Chemical Society, 2006, vol. 128, # 39, p. 12628 - 12629]
[2]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 29
-
[ 52959-28-1 ]
-
[ 939374-74-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C
3: 69 percent / EDCI; DMAP / CH2Cl2 / 3 h / 20 °C |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 30
-
[ 52959-28-1 ]
-
[ 939374-75-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C
3: 69 percent / EDCI; DMAP / CH2Cl2 / 3 h / 20 °C
4: 95 percent / potassium hydroxide / methanol; H2O / 3 h / Heating |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 31
-
[ 52959-28-1 ]
-
[ 939374-76-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C
3: 62 percent / EDCI / CH2Cl2 / 4 h / 20 °C |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 32
-
[ 52959-28-1 ]
-
[ 939374-71-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 33
-
[ 52959-28-1 ]
-
[ 939374-72-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C
3: 36 percent / DMAP; EDCI / CH2Cl2 / 5 h / 20 °C |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 34
-
[ 52959-28-1 ]
-
C30H49N5O10
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 82 percent / potassium carbonate / acetone / 36 h / Heating
2: 89 percent / hydrated hydrazine / methanol / 0.5 h / 20 °C
3: 38 percent / DMAP; EDCI / CH2Cl2 / 5 h / 20 °C |
|
Reference:
[1]Li, Chuang; Wang, Gui-Tao; Yi, Hui-Ping; Jiang, Xi-Kui; Li, Zhan-Ting; Wang, Ren-Xiao
[Organic Letters, 2007, vol. 9, # 9, p. 1797 - 1800]
- 35
-
[ 52959-28-1 ]
-
4,6-bis[2-(3-methyl-butoxy)-ethoxy]-isophthalic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: anhydrous K2CO3 / dimethylformamide / 72 h / 100 °C
2: 4.26 g / NaOH / methanol / 2 h / Heating |
|
- 36
-
[ 52959-28-1 ]
-
{2-[5-(2-<i>tert</i>-butoxycarbonylamino-ethoxy)-2,4-bis-chlorocarbonyl-phenoxy]-ethyl}-carbamic acid <i>tert</i>-butyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 78 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 48 h / 20 °C
2: 84 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 24 h
3: oxalyl chloride; pyridine / tetrahydrofuran; dimethylformamide / 0.75 h |
|
Reference:
[1]Choi, Sungwook; Clements, Dylan J.; Pophristic, Vojislava; Ivanov, Ivaylo; Vemparala, Satyavani; Bennett, Joel S.; Klein, Michael L.; Winkler, Jeffrey D.; DeGrado, William F.
[Angewandte Chemie - International Edition, 2005, vol. 44, # 41, p. 6685 - 6689]
- 37
-
[ 52959-28-1 ]
-
[ 872675-27-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 78 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 48 h / 20 °C
2: 84 percent / lithium hydroxide / methanol; tetrahydrofuran; H2O / 24 h |
|
Reference:
[1]Choi, Sungwook; Clements, Dylan J.; Pophristic, Vojislava; Ivanov, Ivaylo; Vemparala, Satyavani; Bennett, Joel S.; Klein, Michael L.; Winkler, Jeffrey D.; DeGrado, William F.
[Angewandte Chemie - International Edition, 2005, vol. 44, # 41, p. 6685 - 6689]
- 38
-
[ 52959-28-1 ]
-
[ 890705-79-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 79 percent / pyridine / CH2Cl2 / 0.67 h / 20 °C
2: 88 percent / triethylamine; CuI / Pd(dppf)Cl2 / tetrahydrofuran / 45 °C
3: 56 percent / ammonia / ethanol / 140 °C
4: 42 percent / phosphorus oxybromide; potassium carbonate / acetonitrile / 5 h / Heating |
|
- 39
-
[ 52959-28-1 ]
-
[ 890705-78-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 79 percent / pyridine / CH2Cl2 / 0.67 h / 20 °C
2: 88 percent / triethylamine; CuI / Pd(dppf)Cl2 / tetrahydrofuran / 45 °C
3: 56 percent / ammonia / ethanol / 140 °C |
|
- 40
-
[ 52959-28-1 ]
-
[ 890705-74-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: 79 percent / pyridine / CH2Cl2 / 0.67 h / 20 °C
2.1: 88 percent / triethylamine; CuI / Pd(dppf)Cl2 / tetrahydrofuran / 45 °C
3.1: 56 percent / ammonia / ethanol / 140 °C
4.1: 42 percent / phosphorus oxybromide; potassium carbonate / acetonitrile / 5 h / Heating
5.1: n-butyllithium; ZnCl2 / hexane; tetrahydrofuran / -78 - 20 °C
5.2: 80 percent / Pd(P(C6H5)3)4 / tetrahydrofuran; hexane / Heating |
|
- 41
-
[ 52959-28-1 ]
-
[ 890705-77-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 79 percent / pyridine / CH2Cl2 / 0.67 h / 20 °C
2: 88 percent / triethylamine; CuI / Pd(dppf)Cl2 / tetrahydrofuran / 45 °C |
|
- 42
-
[ 52959-28-1 ]
-
4,6-di(isobutoxy)isophthalic acid monomethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 85 percent / K2CO3 / dimethylformamide / 48 h / Heating
2: 62.6 percent / NaOH / H2O; tetrahydrofuran / 12 h / 20 °C |
|
|
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 100 °C
2: potassium hydroxide / methanol; dimethyl sulfoxide / 8 h / 100 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[2]Bie, Fusheng; Wang, Ying; Shang, Jie; Gallagher, Nolan M.; Jiang, Hua
[European Journal of Organic Chemistry, 2013, # 36, p. 8135 - 8144]
- 43
-
[ 52959-28-1 ]
-
[ 874210-36-3 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 85 percent / K2CO3 / dimethylformamide / 48 h / Heating
2: 91 percent / KOH / H2O; methanol / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 44
-
[ 52959-28-1 ]
-
4,6-bis-(3-carboxy-propoxy)-isophthalic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 85.1 percent / K2CO3; KI / dimethylformamide / 48 h / Heating
2: 10 percent / lithium hydroxide monohydrate / methanol / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 45
-
[ 52959-28-1 ]
-
5-Chlorocarbonyl-2,4-bis-[(S)-2-(3-methyl-butoxy)-propoxy]-benzoic acid methyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating
3: oxalyl chloride; DMF / CH2Cl2 / 1 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 46
-
[ 52959-28-1 ]
-
2,4-bis((S)-2-(isopentyloxy)propoxy)-5-(methoxycarbonyl)benzoic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 47
-
[ 52959-28-1 ]
-
4,6-Bis-[(S)-2-(3-methyl-butoxy)-propoxy]-isophthaloyl dichloride
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 83.3 percent / KOH / H2O; methanol / Heating
3: oxalyl chloride; DMF / CH2Cl2 |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 48
-
[ 52959-28-1 ]
-
4,6-bis[2-(3-methylbutoxy)propoxy]isophthalic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 83.3 percent / KOH / H2O; methanol / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 49
-
[ 52959-28-1 ]
-
4,6-bis-(3-<i>tert</i>-butoxycarbonyl-propoxy)-isophthalic acid monomethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 85.1 percent / K2CO3; KI / dimethylformamide / 48 h / Heating
2: 72 percent / lithium hydroxide monohydrate / methanol / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 50
-
[ 52959-28-1 ]
-
4,6-bis[3-(tert-butoxycarbonyl)propoxy]isophthalic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 85.1 percent / K2CO3; KI / dimethylformamide / 48 h / Heating
2: 5 percent / lithium hydroxide monohydrate / methanol / 20 °C |
|
|
Multi-step reaction with 2 steps
1: 85.1 percent / K2CO3; KI / dimethylformamide / 48 h / Heating
2: 15 percent / lithium hydroxide monohydrate / H2O; methanol / 15 h / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[2]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 51
-
[ 52959-28-1 ]
-
4,6-bis[3-(tert-butoxycarbonylamino)propoxy]isophthalic acid
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 86.6 percent / K2CO3; KI / dimethylformamide / 36 h / 90 °C
2: 93.9 percent / NaOH / H2O; methanol; tetrahydrofuran / 1 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 52
-
[ 52959-28-1 ]
-
<i>N</i>,<i>N</i>'-bis-(5-amino-2,4-dimethoxy-phenyl)-4,6-bis-[2-(3-methyl-butoxy)-propoxy]-isophthalamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 83.3 percent / KOH / H2O; methanol / Heating
3: oxalyl chloride; DMF / CH2Cl2
4: triethylamine / CH2Cl2 / 20 °C
5: H2 / Pd/C / ethanol; CHCl3 / 4 h / 48 °C / 0.03 Torr |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 53
-
[ 52959-28-1 ]
-
<i>N</i>,<i>N</i>'-bis-(2,4-dimethoxy-5-nitro-phenyl)-4,6-bis-[2-(3-methyl-butoxy)-propoxy]-isophthalamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 83.3 percent / KOH / H2O; methanol / Heating
3: oxalyl chloride; DMF / CH2Cl2
4: triethylamine / CH2Cl2 / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 54
-
[ 52959-28-1 ]
-
C56H82Cl2N2O14
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 6 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating
3: oxalyl chloride; DMF / CH2Cl2 / 1 h / Heating
4: 2.18 g / triethylamine / CH2Cl2 / 6 h / 20 °C
5: 86.2 percent / KOH / H2O / 3 h / Heating
6: oxalyl chloride; DMF / CH2Cl2 |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 55
-
[ 52959-28-1 ]
-
C58H88N2O16
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating
3: oxalyl chloride; DMF / CH2Cl2 / 1 h / Heating
4: 2.18 g / triethylamine / CH2Cl2 / 6 h / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 56
-
[ 52959-28-1 ]
-
C56H84N2O16
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating
3: oxalyl chloride; DMF / CH2Cl2 / 1 h / Heating
4: 2.18 g / triethylamine / CH2Cl2 / 6 h / 20 °C
5: 86.2 percent / KOH / H2O / 3 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 57
-
[ 52959-28-1 ]
-
C72H100N6O22
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 7 steps
1: 54.5 percent / K2CO3 / dimethylformamide / 48 h / 100 °C
2: 68.6 percent / KOH / H2O; methanol / 3 h / Heating
3: oxalyl chloride; DMF / CH2Cl2 / 1 h / Heating
4: 2.18 g / triethylamine / CH2Cl2 / 6 h / 20 °C
5: 86.2 percent / KOH / H2O / 3 h / Heating
6: oxalyl chloride; DMF / CH2Cl2
7: 0.20 g / triethylamine / CH2Cl2 / 20 °C |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 58
-
[ 52959-28-1 ]
-
[ 7168-99-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 93 percent / K2CO3 / acetone / 72 h / Heating
2: 92.1 percent / NaOH / methanol; H2O / 4 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
- 59
-
[ 52959-28-1 ]
-
[ 267897-58-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 88 percent / K2CO3 / dimethylformamide / 48 h / Heating
2: 96 percent / KOH / tetrahydrofuran; H2O / 2 h / Heating |
|
|
Multi-step reaction with 2 steps
1: 88 percent / K2CO3 / dimethylformamide; methanol / 48 h / 100 °C
2: 93 percent / aq. NaOH / methanol / 0.67 h / Heating |
|
Reference:
[1]Yuan, Lihua; Sanford, Adam R.; Feng, Wen; Zhang, Aimin; Zhu, Jin; Zeng, Huaqiang; Yamato, Kazuhiro; Li, Minfeng; Ferguson, Joseph S.; Gong, Bing
[Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10660 - 10669]
[2]Zeng, Huaqiang; Miller, Rebecca S.; Flowers II, Robert A.; Gong, Bing
[Journal of the American Chemical Society, 2000, vol. 122, # 11, p. 2635 - 2644]
- 60
-
[ 52959-28-1 ]
-
[ 345625-94-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 88 percent / K2CO3 / methanol; dimethylformamide / 48 h / 100 °C
2: 61 percent / KOH / dimethylsulfoxide; methanol / 3 h / 130 °C |
|
|
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide; methanol / 16 h / 100 °C
2: sodium hydroxide / methanol / 48 h / 80 °C |
|
Reference:
[1]Zeng; Ickes; Flowers II; Gong
[Journal of Organic Chemistry, 2001, vol. 66, # 10, p. 3574 - 3583]
[2]Montarnal, Damien; Delbosc, Nicolas; Chamignon, Cécile; Virolleaud, Marie-Alice; Luo, Yingdong; Hawker, Craig J.; Drockenmuller, Eric; Bernard, Julien
[Angewandte Chemie - International Edition, 2015, vol. 54, # 38, p. 11117 - 11121][Angew. Chem., 2016, vol. 127, # 38, p. 11269 - 11273]
- 61
-
[ 52959-28-1 ]
-
[ 267897-60-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: 88 percent / K2CO3 / dimethylformamide; methanol / 48 h / 100 °C
2: 93 percent / aq. NaOH / methanol / 0.67 h / Heating
3: 69 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole; Et3N / dimethylformamide / 6 h
4: 90 percent / aq. NaOH / methanol / 0.67 h / Heating |
|
- 62
-
[ 52959-28-1 ]
-
[ 267897-59-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: 88 percent / K2CO3 / dimethylformamide; methanol / 48 h / 100 °C
2: 93 percent / aq. NaOH / methanol / 0.67 h / Heating
3: 69 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole; Et3N / dimethylformamide / 6 h |
|
- 63
-
[ 52959-28-1 ]
-
N,N'-bis[(((3'-((hexylamino)carbonyl)-4-(octyloxy)phenyl)amino)carbonyl)methyl]-4,6-bis(octyloxy)-1,3-benzenedicarboxamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: 88 percent / K2CO3 / dimethylformamide; methanol / 48 h / 100 °C
2: 93 percent / aq. NaOH / methanol / 0.67 h / Heating
3: 69 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole; Et3N / dimethylformamide / 6 h
4: 90 percent / aq. NaOH / methanol / 0.67 h / Heating
5: 79 percent / 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide*HCl; 1-hydroxybenzotriazole / dimethylformamide / 6 h / 20 °C |
|
- 64
-
[ 108-46-3 ]
-
[ 52959-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: 45 percent / 3 h / 210 °C
2: 90 percent / conc. H2SO4 / 48 h / Heating |
|
- 65
-
[ 15540-79-1 ]
-
[ 52959-28-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: NaNO2; aqueous H2SO4 / Erwaermen des Reaktionsgemisches mit wss. H2SO4
2: diethyl ether; ethanol |
|
- 66
-
C21H41ClN2O2
[ No CAS ]
-
[ 52959-28-1 ]
-
[ 1031691-56-1 ]
Yield | Reaction Conditions | Operation in experiment |
76% |
With potassium carbonate; potassium iodide In acetone for 7h; Heating; |
|
- 67
-
[ 1031691-45-8 ]
-
[ 52959-28-1 ]
-
[ 1031691-51-6 ]
Yield | Reaction Conditions | Operation in experiment |
81% |
Stage #1: dimethyl 4,6-dihydroxyisophthalate With potassium carbonate In acetone for 0.5h;
Stage #2: 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethyl chloride With potassium iodide In acetone for 7h; Heating; Further stages.; |
|
- 68
-
[ 112-29-8 ]
-
[ 52959-28-1 ]
-
[ 1052717-00-6 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; |
|
Reference:
[1]Cai, Wei; Wang, Gui-Tao; Du, Ping; Wang, Ren-Xiao; Jiang, Xi-Kui; Li, Zhan-Ting
[Journal of the American Chemical Society, 2008, vol. 130, # 40, p. 13450 - 13459]
- 69
-
[ 52959-28-1 ]
-
[ 192378-93-1 ]
-
[ 1156504-65-2 ]
Yield | Reaction Conditions | Operation in experiment |
35% |
With tetrabutylammomium bromide; potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 80℃; for 168h; Inert atmosphere; |
|
Reference:
[1]Zhu, Kelong; He, Jiuming; Li, Shijun; Liu, Ming; Wang, Feng; Zhang, Mingming; Abliz, Zeper; Yang, Hai-Bo; Li, Ning; Huang, Feihe
[Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3905 - 3912]
- 70
-
[ 52959-28-1 ]
-
[ 109-73-9 ]
-
[ 1031691-43-6 ]
Yield | Reaction Conditions | Operation in experiment |
45% |
In N,N-dimethyl-formamide at 75℃; for 7h; |
|
- 71
-
[ 52959-28-1 ]
-
[ 1359296-24-4 ]
-
[ 1359296-32-4 ]
Yield | Reaction Conditions | Operation in experiment |
76.4% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; |
|
Reference:
[1]Wu, Xiangxiang; Liang, Guoxing; Ji, Gang; Fun, Hoong-Kun; He, Lan; Gong, Bing
[Chemical Communications, 2012, vol. 48, # 16, p. 2228 - 2230]
- 72
-
[ 52959-28-1 ]
-
[ 107-82-4 ]
-
[ 1359296-31-3 ]
Yield | Reaction Conditions | Operation in experiment |
70% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; |
|
Reference:
[1]Wu, Xiangxiang; Liang, Guoxing; Ji, Gang; Fun, Hoong-Kun; He, Lan; Gong, Bing
[Chemical Communications, 2012, vol. 48, # 16, p. 2228 - 2230]
- 73
-
[ 52959-28-1 ]
-
[ 87549-18-6 ]
-
[ 1454693-35-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: dimethyl 4,6-dihydroxyisophthalate; 2-hexyldecyl-4-methylbenzene sulfonate With potassium carbonate In N,N-dimethyl-formamide
Stage #2: With potassium hydroxide In methanol; water
Stage #3: With hydrogenchloride In methanol; water |
|
Reference:
[1]Hu, Jinchuan; Chen, Long; Ren, Yi; Deng, Pengchi; Li, Xiaowei; Wang, Youjia; Jia, Yiming; Luo, Jian; Yang, Xinshi; Feng, Wen; Yuan, Lihua
[Organic Letters, 2013, vol. 15, # 18, p. 4670 - 4673]
- 74
-
[ 52959-28-1 ]
-
[ 87549-18-6 ]
-
[ 1454693-36-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide
2: oxalyl dichloride / dichloromethane |
|
Reference:
[1]Hu, Jinchuan; Chen, Long; Ren, Yi; Deng, Pengchi; Li, Xiaowei; Wang, Youjia; Jia, Yiming; Luo, Jian; Yang, Xinshi; Feng, Wen; Yuan, Lihua
[Organic Letters, 2013, vol. 15, # 18, p. 4670 - 4673]
- 75
-
[ 52959-28-1 ]
-
[ 1373944-94-5 ]
-
[ 1454693-40-3 ]
Yield | Reaction Conditions | Operation in experiment |
43 mg |
With triethylamine In dichloromethane at -20℃; Inert atmosphere; |
|
Reference:
[1]Hu, Jinchuan; Chen, Long; Ren, Yi; Deng, Pengchi; Li, Xiaowei; Wang, Youjia; Jia, Yiming; Luo, Jian; Yang, Xinshi; Feng, Wen; Yuan, Lihua
[Organic Letters, 2013, vol. 15, # 18, p. 4670 - 4673]
- 76
-
[ 52959-28-1 ]
-
[ 1454709-91-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C |
|
- 77
-
[ 52959-28-1 ]
-
[ 1454709-92-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C |
|
- 78
-
[ 52959-28-1 ]
-
[ 1454709-94-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C |
|
|
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 80 °C |
|
Reference:
[1]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
[2]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
- 79
-
[ 52959-28-1 ]
-
[ 1454710-02-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 20 °C
4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: potassium hydroxide; water / methanol / 72 h / Reflux |
|
- 80
-
[ 52959-28-1 ]
-
[ 1454710-03-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C
4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
5.1: potassium hydroxide; water / methanol / 72 h / Reflux |
|
- 81
-
[ 52959-28-1 ]
-
[ 1454709-98-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 20 °C
4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere |
|
- 82
-
[ 52959-28-1 ]
-
[ 1454709-99-9 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C
4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere |
|
- 83
-
[ 52959-28-1 ]
-
[ 1454710-10-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
5.1: trifluoroacetic acid / 20 °C |
|
|
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 80 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
5.1: trifluoroacetic acid / 20 °C |
|
Reference:
[1]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
[2]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
- 84
-
[ 52959-28-1 ]
-
[ 1454710-06-5 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere |
|
|
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 80 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere |
|
Reference:
[1]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
[2]Kline, Mark; Wei, Xiaoxi; Gong, Bing
[Organic Letters, 2013, vol. 15, # 18, p. 4762 - 4765]
- 85
-
[ 52959-28-1 ]
-
[ 1454710-11-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 80 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
5.1: trifluoroacetic acid / 20 °C |
|
- 86
-
[ 52959-28-1 ]
-
[ 1454710-07-6 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 80 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h
4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere |
|
- 87
-
[ 52959-28-1 ]
-
C19H27ClO5
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
1.2: 72 h / 100 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 20 °C |
|
- 88
-
[ 52959-28-1 ]
-
C17H23ClO5
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h
1.2: 48 h / 80 °C
2.1: potassium hydroxide; water / methanol / 24 h / 60 °C
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C |
|