Alternatived Products of [ 107428-05-7 ]
Product Details of [ 107428-05-7 ]
CAS No. : | 107428-05-7 |
MDL No. : | |
Formula : |
C13H16O4
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
236.26
|
Pubchem ID : | - |
Synonyms : |
|
Safety of [ 107428-05-7 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 107428-05-7 ]
* 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 [ 107428-05-7 ]
- 1
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[ 107428-05-7 ]
-
[ 16356-02-8 ]
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5,6-bis-methoxymethyl-4,7-dimethyl-indan-2,2-dicarboxylic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With 1,2-bis-(diphenylphosphino)ethane In benzene at 20℃; for 0.5h; |
|
94% |
With 1,2-bis-(diphenylphosphino)ethane In benzene at 20℃; for 0.5h; |
|
Reference:
[1]Takeuchi, Ryo; Tanaka, Shigeru; Nakaya, Yoshihiko
[Tetrahedron Letters, 2001, vol. 42, # 16, p. 2991 - 2994]
[2]Kezuka, Satoko; Tanaka, Shigeru; Ohe, Toshihito; Nakaya, Yoshihiko; Takeuchi, Ryo
[Journal of Organic Chemistry, 2006, vol. 71, # 2, p. 543 - 552]
- 2
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[ 107428-05-7 ]
-
[ 1548-13-6 ]
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dimethyl 1,4-dimethyl-3-oxo-2-(4-trifluoromethylphenyl)-5H-2,3,6,7-tetrahydrocyclopenta[c]pyridine-6,6-dicarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
84% |
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In toluene at 80℃; for 0.5h; |
|
72% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,2-Dichloropropane for 24h; Inert atmosphere; Reflux; |
|
Reference:
[1]Duong, Hung A.; Cross, Michael J.; Louie, Janis
[Journal of the American Chemical Society, 2004, vol. 126, # 37, p. 11438 - 11439]
[2]Location in patent: experimental part
Onodera, Gen; Suto, Mari; Takeuchi, Ryo
[Journal of Organic Chemistry, 2012, vol. 77, # 2, p. 908 - 920]
- 3
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[ 455-18-5 ]
-
[ 107428-05-7 ]
-
dimethyl 1,4-dimethyl-3-(4-(trifluoromethyl)phenyl)-5H-cyclopenta[c]pyridine-6,6(7H)-dicarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
98% |
With bis(1,5-cyclooctadiene)nickel (0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 3h; Inert atmosphere; |
|
94% |
With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene In toluene at 20℃; for 2h; |
|
Reference:
[1]Kumar, Puneet; Prescher, Simon; Louie, Janis
[Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10694 - 10698]
[2]McCormick, Michael M.; Duong, Hung A.; Zuo, Gang; Louie, Janis
[Journal of the American Chemical Society, 2005, vol. 127, # 14, p. 5030 - 5031]
- 4
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[ 52784-31-3 ]
-
[ 107428-05-7 ]
-
dimethyl 2,7-dimethyl-5-phenylbicyclo[6.3.0]undeca-1,7-dien-3-one-10,10-dicarboxylate
[ No CAS ]
- 5
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[ 55756-24-6 ]
-
[ 107428-05-7 ]
-
4,7-dimethyl-5-tridecafluorohexylindane-2,2-dicarboxylic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
85% |
With (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; for 3h; |
|
- 6
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[ 107428-05-7 ]
-
[ 1817-57-8 ]
-
5-acetyl-4,7-dimethyl-6-phenylindan-2,2-dicarboxylic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
99% |
With hydrogen In dichloromethane at 20℃; for 3h; |
|
99% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; hydrogen In dichloromethane at 20℃; for 3h; Inert atmosphere; optical yield given as %de; |
|
Reference:
[1]Tanaka, Ken; Otake, Yousuke; Wada, Azusa; Noguchi, Keiichi; Hirano, Masao
[Organic Letters, 2007, vol. 9, # 11, p. 2203 - 2206]
[2]Otake, Yousuke; Tanaka, Rie; Tanaka, Ken
[European Journal of Organic Chemistry, 2009, # 17, p. 2737 - 2747]
- 7
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[ 107428-05-7 ]
-
[ 611-70-1 ]
-
3-ethylidene-4-[1-(2-isobutyrylphenyl)ethylidene]cyclopentane-1,1-dicarboxylic acid dimethyl ester
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With hydrogen In dichloromethane at 20℃; for 3h; |
|
- 8
-
[ 107428-05-7 ]
-
[ 609-09-6 ]
-
3-acetyl-4-(2,2-bisethoxycarbonyl-1-methylvinyl)cyclopent-3-ene-1,1-dicarboxylic acid dimethyl ester
[ No CAS ]
- 9
-
[ 52784-31-3 ]
-
[ 107428-05-7 ]
-
[ 880551-35-9 ]
- 10
-
[ 56309-56-9 ]
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[ 107428-05-7 ]
-
dimethyl (+)-2-(2-isopropylphenyl)-1,4-dimethyl-3-oxo-5H-2,3,6,7-tetrahydrocyclopenta[c]-pyridine-6,6-dicarboxylate
[ No CAS ]
-
dimethyl (-)-2-(2-isopropylphenyl)-1,4-dimethyl-3-oxo-5H-2,3,6,7-tetrahydrocyclopenta[c]-pyridine-6,6-dicarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
|
|
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2′-bis(diphenylphosphanyl)-5,5′-6,6′-7,7′,8,8′-octahydro-1,1′-binaphthyl In dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
|
|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In benzene at 0℃; for 1h; Inert atmosphere; Reflux; optical yield given as %ee; enantioselective reaction; |
|
4 % ee |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; C50H56O4P(1-)*Ag(1+); 1,4-di(diphenylphosphino)-butane In dichloromethane at 80℃; for 15h; Inert atmosphere; Overall yield = 75 %; Overall yield = 60 mg; enantioselective reaction; |
|
Reference:
[1]Location in patent: experimental part
Tanaka, Ken; Takahashi, Yoshihiro; Suda, Takeshi; Hirano, Masao
[Synlett, 2008, # 11, p. 1724 - 1728]
[2]Location in patent: experimental part
Tanaka, Ken; Takahashi, Yoshihiro; Suda, Takeshi; Hirano, Masao
[Synlett, 2008, # 11, p. 1724 - 1728]
[3]Location in patent: experimental part
Onodera, Gen; Suto, Mari; Takeuchi, Ryo
[Journal of Organic Chemistry, 2012, vol. 77, # 2, p. 908 - 920]
[4]Auge, Mylene; Barbazanges, Marion; Tran, Anh Tuan; Simonneau, Antoine; Elley, Paulin; Amouri, Hani; Aubert, Corinne; Fensterbank, Louis; Gandon, Vincent; Malacria, Max; Moussa, Jamal; Ollivier, Cyril
[Chemical Communications, 2013, vol. 49, # 71, p. 7833 - 7835]
- 11
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[ 872-36-6 ]
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[ 107428-05-7 ]
-
[ 1131477-17-2 ]
- 12
-
[ 13031-04-4 ]
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[ 107428-05-7 ]
-
[ 1173788-18-5 ]
- 13
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[ 20201-24-5 ]
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[ 107428-05-7 ]
-
[ 1173788-05-0 ]
Yield | Reaction Conditions | Operation in experiment |
87% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; hydrogen In dichloromethane at 20℃; for 3h; Inert atmosphere; |
|
- 14
-
[ 2247-91-8 ]
-
[ 107428-05-7 ]
-
[ 1173997-03-9 ]
Yield | Reaction Conditions | Operation in experiment |
22% |
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; 2,2'-bis(diphenylphosphino)biphenyl In dichloromethane at 20℃; for 3h; Inert atmosphere; |
|
- 15
-
[ 107428-05-7 ]
-
[ 27584-70-9 ]
-
[ 1301254-61-4 ]
- 16
-
[ 1530-88-7 ]
-
[ 107428-05-7 ]
-
[ 1323947-44-9 ]
Yield | Reaction Conditions | Operation in experiment |
93% |
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In toluene at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; |
|
91% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 24h; Inert atmosphere; Reflux; |
|
90% |
With 2,6-bis(2,4,6-trimethylphenyliminomethyl)pyridine; iron(II) chloride; zinc In benzene at 70℃; for 6h; Inert atmosphere; regioselective reaction; |
|
85% |
With 1,3-bis-(diphenylphosphino)propane; ferrous iodide; zinc In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
|
81% |
With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate at 20℃; for 0.25h; Sealed tube; Inert atmosphere; |
|
Reference:
[1]Location in patent: experimental part
Stolley, Ryan M.; MacZka, Michael T.; Louie, Janis
[European Journal of Organic Chemistry, 2011, # 20-21, p. 3815 - 3824]
[2]Hashimoto, Toru; Ishii, Satoshi; Yano, Reiko; Miura, Hiroki; Sakata, Ken; Takeuchi, Ryo
[Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3901 - 3916]
[3]Lane, Timothy K.; D'Souza, Brendan R.; Louie, Janis
[Journal of Organic Chemistry, 2012, vol. 77, # 17, p. 7555 - 7563]
[4]Wang, Chunxiang; Wang, Dongping; Xu, Fen; Pan, Bin; Wan, Boshun
[Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3065 - 3072]
[5]Ye, Fei; Haddad, Mansour; Ratovelomanana-Vidal, Virginie; Michelet, Véronique
[Organic Letters, 2017, vol. 19, # 5, p. 1104 - 1107]
- 17
-
[ 1530-89-8 ]
-
[ 107428-05-7 ]
-
[ 1323947-52-9 ]
Yield | Reaction Conditions | Operation in experiment |
99% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 1h; Inert atmosphere; Reflux; |
|
97% |
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In toluene at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; |
|
95% |
With 1,3-bis-(diphenylphosphino)propane; ferrous iodide; zinc In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
|
91% |
With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; |
|
67% |
With 2,6-bis(2,4,6-trimethylphenyliminomethyl)pyridine; iron(II) chloride; zinc In benzene at 70℃; for 5h; Inert atmosphere; regioselective reaction; |
|
Reference:
[1]Hashimoto, Toru; Ishii, Satoshi; Yano, Reiko; Miura, Hiroki; Sakata, Ken; Takeuchi, Ryo
[Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3901 - 3916]
[2]Location in patent: experimental part
Stolley, Ryan M.; MacZka, Michael T.; Louie, Janis
[European Journal of Organic Chemistry, 2011, # 20-21, p. 3815 - 3824]
[3]Wang, Chunxiang; Wang, Dongping; Xu, Fen; Pan, Bin; Wan, Boshun
[Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3065 - 3072]
[4]Ye, Fei; Haddad, Mansour; Ratovelomanana-Vidal, Virginie; Michelet, Véronique
[Organic Letters, 2017, vol. 19, # 5, p. 1104 - 1107]
[5]Lane, Timothy K.; D'Souza, Brendan R.; Louie, Janis
[Journal of Organic Chemistry, 2012, vol. 77, # 17, p. 7555 - 7563]
- 18
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[ 2451-91-4 ]
-
[ 107428-05-7 ]
-
[ 1323947-54-1 ]
Yield | Reaction Conditions | Operation in experiment |
88% |
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In toluene at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; |
|
82% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 1h; Inert atmosphere; Reflux; |
|
|
With 1,3-bis-(diphenylphosphino)propane; ferrous iodide; zinc In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
|
Reference:
[1]Location in patent: experimental part
Stolley, Ryan M.; MacZka, Michael T.; Louie, Janis
[European Journal of Organic Chemistry, 2011, # 20-21, p. 3815 - 3824]
[2]Hashimoto, Toru; Ishii, Satoshi; Yano, Reiko; Miura, Hiroki; Sakata, Ken; Takeuchi, Ryo
[Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3901 - 3916]
[3]Wang, Chunxiang; Wang, Dongping; Xu, Fen; Pan, Bin; Wan, Boshun
[Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3065 - 3072]
- 19
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[ 56309-56-9 ]
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[ 107428-05-7 ]
-
dimethyl (-)-2-(2-isopropylphenyl)-1,4-dimethyl-3-oxo-5H-2,3,6,7-tetrahydrocyclopenta[c]-pyridine-6,6-dicarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
51% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-(+)-2,2'-bis(diphenylphosphanyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl In benzene at 0℃; for 1h; Inert atmosphere; Reflux; optical yield given as %ee; enantioselective reaction; |
|
- 20
-
[ 56309-56-9 ]
-
[ 107428-05-7 ]
-
[ 1450907-28-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
With silver tetrafluoroborate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 20℃; for 18h; Inert atmosphere; |
|
Reference:
[1]Auge, Mylene; Barbazanges, Marion; Tran, Anh Tuan; Simonneau, Antoine; Elley, Paulin; Amouri, Hani; Aubert, Corinne; Fensterbank, Louis; Gandon, Vincent; Malacria, Max; Moussa, Jamal; Ollivier, Cyril
[Chemical Communications, 2013, vol. 49, # 71, p. 7833 - 7835]
- 21
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[ 111-12-6 ]
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[ 107428-05-7 ]
-
trimethyl 4,7-dimethyl-6-pentyl-1H-indene-2,2,5(3H)-tricarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
83% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In benzene; for 2h;Reflux; Inert atmosphere; |
General procedure: Representative procedure for the [222] cycloaddition of diyne 1a with alkynyl ester 4.Aflask was charged with [Ir(cod)Cl]2(7.0 mg, 0.01 mmol) and rac-BINAP (12.2 mg, 0.02 mmol). The flask was evacuated and filled with argon. To the flask were added benzene (5 mL) and methyl 2-undecynoate (4c) (444 mg, 2.3 mmol). Diyne1a(234 mg, 1.0 mmol) was added to the reaction mixture. The mixture was stirred under reflux for 2 h. The progress of the reaction was monitored by GLC. After the reaction was complete, the solvent was evaporated invacuo. Column chromatography of the residue gave 5ac(n-hexane/AcOEt 85:15, 378 mg, 0.87 mmol, 88% yield). |
- 22
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[ 4891-38-7 ]
-
[ 107428-05-7 ]
-
trimethyl 4,7-dimethyl-6-phenyl-1H-indene-2,2,5(3H)-tricarboxylate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
76% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In benzene for 16h; Reflux; Inert atmosphere; |
4.3. Reaction of diyne 1a with alkynyl ester 4
General procedure: Representative procedure for the [222] cycloaddition of diyne 1a with alkynyl ester 4.Aflask was charged with [Ir(cod)Cl]2(7.0 mg, 0.01 mmol) and rac-BINAP (12.2 mg, 0.02 mmol). The flask was evacuated and filled with argon. To the flask were added benzene (5 mL) and methyl 2-undecynoate (4c) (444 mg, 2.3 mmol). Diyne1a(234 mg, 1.0 mmol) was added to the reaction mixture. The mixture was stirred under reflux for 2 h. The progress of the reaction was monitored by GLC. After the reaction was complete, the solvent was evaporated invacuo. Column chromatography of the residue gave 5ac(n-hexane/AcOEt 85:15, 378 mg, 0.87 mmol, 88% yield). |
- 23
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[ 36122-35-7 ]
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[ 107428-05-7 ]
-
dimethyl 4,7-dimethyl-5-phenylindane-2,2-dicarboxylate
[ No CAS ]
- 24
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[ 60710-39-6 ]
-
[ 107428-05-7 ]
-
dimethyl 4,4a,9-trimethyl-7-oxo-1,3,4a,7-tetrahydro-2H-cyclopenta[b]naphthalene-2,2-dicarboxylate
[ No CAS ]