Alternatived Products of [ 69797-46-2 ]
Product Details of [ 69797-46-2 ]
CAS No. : | 69797-46-2 |
MDL No. : | MFCD01320062 |
Formula : |
C10H9FO3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | HHVYNFFVNGZSNG-UHFFFAOYSA-N |
M.W : |
196.18
|
Pubchem ID : | 2759124 |
Synonyms : |
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Application In Synthesis of [ 69797-46-2 ]
* 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.
- Upstream synthesis route of [ 69797-46-2 ]
- Downstream synthetic route of [ 69797-46-2 ]
- 1
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[ 69797-46-2 ]
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[ 106-48-9 ]
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[ 57148-29-5 ]
Yield | Reaction Conditions | Operation in experiment |
10 g |
With potassium carbonate In N,N-dimethyl acetamide at 135℃; for 16h; |
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- 2
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2-(3-Fluoro-phenyl)-2-morpholin-4-yl-pentanedinitrile
[ No CAS ]
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[ 69797-46-2 ]
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride In hexane for 1h; Heating; Yield given; |
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Yield | Reaction Conditions | Operation in experiment |
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entspr. Methylester, H2SO4; |
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β-(3-Aminobenzoyl)-propionsaeure, NaNO2, HCl, HPF6; |
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64 1-[3-Acetylthio-3-(3-fluorobenzoyl)propionyl]-L-proline
EXAMPLE 64 1-[3-Acetylthio-3-(3-fluorobenzoyl)propionyl]-L-proline 3-(3-Fluorobenzoyl)propionic acid is prepared from 3-fluorobenzoldehyde as for Example 47 to give yellow needles m.p. 97°-99° C. |
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Examples of compounds of formula (I) either as single enantiomer or as mixture of enantiomers, are listed below: 4-(3'-chlorophenyl)-4-oxo-butanoic acid; 4-(3'-fluorophenyl)-4-oxo-butanoic acid; 4-(3'-bromophenyl)-4-oxo-butanoic acid; 4-(3'-nitrophenyl)-4-oxo-butanoic acid; 4-(3',4'-dichlorophenyl)-4-oxo-butanoic acid; Methyl 4-(3',4'-dichlorophenyl)-4-oxo-butanoate; 4-(3',4'-difluorophenyl)-4-oxo-butanoic acid; 4-(3'-nitro-4'-fluorophenyl)-4-oxo-butanoic acid; 4-(3'-nitro-4'-chlorophenyl)-4-oxo-butanoic acid; ... |
- 4
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[ 66549-02-8 ]
-
[ 69797-46-2 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: 1.) 30 percent KOH / 1.) THF, EtOH, 18 h, 2.) H2O, acetic acid, reflux, 1 h
2: 6 N HCl / hexane / 1 h / Heating |
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- 5
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[ 69797-46-2 ]
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N-[3-acetylthio-3-(3-fluorobenzoyl)propionyl]-L-valine
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
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32 N-[3-Acetylthio-3-(3-fluorobenzoyl)propionyl]-L-valine
EXAMPLE 32 N-[3-Acetylthio-3-(3-fluorobenzoyl)propionyl]-L-valine Substitution of 3-(3-fluorobenzoyl)propionic acid for 3-(4-bromobenzoyl)propionic acid in the procedure of Example 1 produces N-[3-acetylthio-3-(3-fluorobenzoyl)propionyl]-L-valine. |
- 6
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[ 108-30-5 ]
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[ 17318-03-5 ]
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[ 69797-46-2 ]
Yield | Reaction Conditions | Operation in experiment |
80% |
With Aluminum Chloride In tetrahydrofuran at -40 - 20℃; for 13h; Inert atmosphere; |
|
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Stage #1: succinic acid anhydride; 3-Fluorophenylmagnesium bromide In tetrahydrofuran at -78 - 20℃; for 4h;
Stage #2: With hydrogenchloride; water monomer In tetrahydrofuran |
Succinic anhydride (4.7 g, 47 mmol) was suspended in THF and cooled to -78 0C. 3-Fluorophenylmagnesium bromide was added slowly and the reaction was stirred for 2 h at -78 0C and then for 2 h at room temperature. The reaction mixture was poured into 1M HCI and extracted with DCM. The combined organic phases were dried (MgSO4), filtered and evaporated. LC/MS (an20n5): Rt 1.5 min, m/z 195 [M-H]. 1H NMR (CDCI3) δ 2.82 (t, 2H), 3.30 (t, 2H), 7.27 (m, 1H)1 7.46 (m, 1H), 7.65 (m, 1 H), 7.76 (m, 1 H). |
Reference:
[1]Guo, Qianling; Hou, Guohua; Huang, Yuping; Xiao, Guiying; Xie, Chaochao; Zi, Guofu
[Organic Letters, 2022, vol. 24, # 14, p. 2722 - 2727]
[2]Current Patent Assignee: 7TM PHARMA AS - WO2007/62797, 2007, A1
Location in patent: Page/Page column 25
- 7
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[ 69797-46-2 ]
-
[ 870862-09-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
With bromine In diethyl ether at 20℃; for 4h; |
4-(3-Fluorophenyl)-4-oxobutyric acid (2.19 g, 11.2 mmol) was dissolved in ether at room temperature. Bromine (0.55 ml_, 11.2 mmol) was added drop-wise. After 4 hours the solvent was removed under vaccum and stripped with ACN. Finally the product was purified on a PEAX SPE column (equilibrated with 100% MeOH and then eluted with 5% AcOH in MeOH) to give the product. |
- 8
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[ 69797-46-2 ]
-
[ 62-53-3 ]
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C16H14FNO2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 0.333333h; |
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Reference:
[1]Location in patent: scheme or table
Webster, Scott P.; Binnie, Margaret; McConnell, Kirsty M.M.; Sooy, Karen; Ward, Peter; Greaney, Michael F.; Vinter, Andy; Pallin, T. David; Dyke, Hazel J.; Gill, Matthew I.A.; Warner, Ines; Seckl, Jonathan R.; Walker, Brian R.
[Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 11, p. 3265 - 3271]
- 9
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[ 69797-46-2 ]
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[ 70631-88-8 ]
Yield | Reaction Conditions | Operation in experiment |
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With palladium 10% on activated carbon; hydrogen In acetic acid at 70℃; |
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With hydrogen; palladium |
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Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
[2]Current Patent Assignee: MITOKININ - WO2021/168446, 2021, A1
Location in patent: Paragraph 0328; 0416
- 10
-
[ 69797-46-2 ]
-
[ 13790-88-0 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 11
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[ 69797-46-2 ]
-
C10H10FNO
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 12
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[ 69797-46-2 ]
-
N-((6aR,11aS)-2-fluoro-8-(4-methylphenylsulfonamido)-5,6,6a,11a-tetrahydronaphtho[1,2-b]benzofuran-11a-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C
5: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / dichloromethane / 12 h / 0 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 13
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[ 69797-46-2 ]
-
N-((6aR,11aS)-4-fluoro-8-(4-methylphenylsulfonamido)-5,6,6a,11a-tetrahydronaphtho[1,2-b]benzofuran-11a-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C
5: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / dichloromethane / 12 h / 0 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 14
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[ 69797-46-2 ]
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C25H23FN2O4S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C
5: (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate / 20 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 15
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[ 69797-46-2 ]
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C25H23FN2O4S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 5 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C
5: (R)-3,3'-bis(2,4,6-triisopropylphenyl)-1,1'-binaphthyl-2,2'-diylhydrogenphosphate / 20 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 16
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[ 69797-46-2 ]
-
[ 2840-44-0 ]
- 17
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[ 69797-46-2 ]
-
[ 93742-85-9 ]
- 18
-
[ 69797-46-2 ]
-
N-(7-fluoro-3,4-dihydronaphthalen-1-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 19
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[ 69797-46-2 ]
-
N-(5-fluoro-3,4-dihydronaphthalen-1-yl)acetamide
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1: palladium 10% on activated carbon; hydrogen / acetic acid / 70 °C
2: polyphosphoric acid / 90 °C
3: sodium acetate; hydroxylamine hydrochloride / methanol / 2 h / 60 °C
4: acetic acid; iron / toluene / 5 h / 75 °C |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 20
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[ 108-30-5 ]
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[ 462-06-6 ]
-
[ 69797-46-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: fluorobenzene With aluminum (III) chloride In nitrobenzene at 20℃; for 0.5h;
Stage #2: succinic acid anhydride In nitrobenzene at 60℃; |
|
Reference:
[1]Zhang, Minmin; Yu, Shuowen; Hu, Fangzhi; Liao, Yijun; Liao, Lihua; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei
[Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760]
- 21
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[ 69797-46-2 ]
-
(R)-5-(3-fluorophenyl)dihydrofuran-2(3H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
97% |
With C86H80Cl4N2O2P2Ru3; hydrogen; triphenylphosphine; potassium hydroxide In isopropyl alcohol at 20℃; for 24h; Autoclave; enantioselective reaction; |
|
Reference:
[1]Li, Jing; Ma, Yujie; Lu, Yufei; Liu, Yangang; Liu, Delong; Zhang, Wanbin
[Advanced Synthesis and Catalysis, 2019, vol. 361, # 5, p. 1146 - 1153]
- 22
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[ 69797-46-2 ]
-
[ 1270585-10-8 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium tetrahydroborate In methanol at 20℃; Inert atmosphere; |
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Reference:
[1]Li, Jing; Ma, Yujie; Lu, Yufei; Liu, Yangang; Liu, Delong; Zhang, Wanbin
[Advanced Synthesis and Catalysis, 2019, vol. 361, # 5, p. 1146 - 1153]
- 23
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[ 69797-46-2 ]
-
[ 75-65-0 ]
-
tert-butyl 4-(3-fluorophenyl)-4-oxobutanoate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
68% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; |
|
Reference:
[1]Shi, Yongjie; Tan, Xuefeng; Gao, Shuang; Zhang, Yao; Wang, Jingxin; Zhang, Xumu; Yin, Qin
[Organic Letters, 2020, vol. 22, # 7, p. 2707 - 2713]
- 24
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[ 69797-46-2 ]
-
(R)-5-(3-fluorophenyl)pyrrolidin-2-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
2: Ru(2+)*2C2H3O2(1-)*C77H108O6P2; hydrogen; ammonium acetate / 2,2,2-trifluoroethanol / 24 h / 90 °C / Autoclave |
|
Reference:
[1]Shi, Yongjie; Tan, Xuefeng; Gao, Shuang; Zhang, Yao; Wang, Jingxin; Zhang, Xumu; Yin, Qin
[Organic Letters, 2020, vol. 22, # 7, p. 2707 - 2713]
- 25
-
[ 69797-46-2 ]
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(S)-5-(3-fluorophenyl)dihydrofuran-2(3H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
86% |
With (R,R)-(−)-2,3-bis(t-butylmethylphosphino)quinoxaline; hydrogen; palladium diacetate; zinc trifluoromethanesulfonate In 1,2-dichloro-ethane at 70℃; for 35h; enantioselective reaction; |
|
Reference:
[1]Zhang, Keyang; Zhang, Xuexin; Chen, Jingchao; Liu, Zixiu; Pan, Chunxiang; Zhu, Yuanbin; Wu, Shiyuan; Fan, Baomin
[Chemistry - An Asian Journal, 2021, vol. 16, # 10, p. 1229 - 1232]
- 26
-
[ 69797-46-2 ]
-
(R)-5-(3-fluorophenyl)dihydrofuran-2(3H)-one
[ No CAS ]
-
(S)-5-(3-fluorophenyl)dihydrofuran-2(3H)-one
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
87% ee |
With Ni(ClO4)2·6H2O; (S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline; hydrogen In <i>tert</i>-butyl alcohol at 45℃; for 24h; Autoclave; Overall yield = 91 percent; Overall yield = 32.8 mg; enantioselective reaction; |
|
|
With (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline; hydrogen; nickel(II) acetate tetrahydrate In 2,2,2-trifluoroethanol at 60℃; for 24h; Glovebox; Autoclave; Overall yield = 98 percent; Overall yield = 22 mg; Optical yield = 80 percent ee; enantioselective reaction; |
|
Reference:
[1]Deng, Chen-Qiang; Deng, Jin
[Organic Letters, 2022, vol. 24, # 13, p. 2494 - 2498]
[2]Guo, Qianling; Hou, Guohua; Huang, Yuping; Xiao, Guiying; Xie, Chaochao; Zi, Guofu
[Organic Letters, 2022, vol. 24, # 14, p. 2722 - 2727]
- 27
-
[ 1073-06-9 ]
-
[ 69797-46-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: magnesium / tetrahydrofuran; diethyl ether / 50 °C / Inert atmosphere
2: Aluminum Chloride / tetrahydrofuran / 13 h / -40 - 20 °C / Inert atmosphere |
|
Reference:
[1]Guo, Qianling; Hou, Guohua; Huang, Yuping; Xiao, Guiying; Xie, Chaochao; Zi, Guofu
[Organic Letters, 2022, vol. 24, # 14, p. 2722 - 2727]
- 28
-
[ 69797-46-2 ]
-
(+)-methyl 4-(3-fluorophenyl)-4-hydroxybutanoate
[ No CAS ]
-
(-)-methyl 4-(3-fluorophenyl)-4-hydroxybutanoate
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 24 h / 0 - 20 °C
2: (R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline; nickel(II) acetate tetrahydrate; hydrogen / 2,2,2-trifluoroethanol / 24 h / 25 °C / Glovebox; Autoclave |
|
Reference:
[1]Guo, Qianling; Hou, Guohua; Huang, Yuping; Xiao, Guiying; Xie, Chaochao; Zi, Guofu
[Organic Letters, 2022, vol. 24, # 14, p. 2722 - 2727]
- 29
-
[ 67-56-1 ]
-
[ 69797-46-2 ]
-
[ 69797-47-3 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; |
|
Reference:
[1]Guo, Qianling; Hou, Guohua; Huang, Yuping; Xiao, Guiying; Xie, Chaochao; Zi, Guofu
[Organic Letters, 2022, vol. 24, # 14, p. 2722 - 2727]