Alternatived Products of [ 73246-30-7 ]
Product Details of [ 73246-30-7 ]
CAS No. : 73246-30-7
MDL No. : MFCD01677284
Formula :
C9 H9 F2 NO3
Boiling Point :
-
Linear Structure Formula : -
InChI Key : KPKMCRFCNWVLDA-ZETCQYMHSA-N
M.W :
217.17
Pubchem ID : 21764745
Synonyms :
Calculated chemistry of [ 73246-30-7 ]
Physicochemical Properties
Num. heavy atoms :
15
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.22
Num. rotatable bonds :
3
Num. H-bond acceptors :
6.0
Num. H-bond donors :
3.0
Molar Refractivity :
47.44
TPSA :
83.55 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
No
P-gp substrate :
No
CYP1A2 inhibitor :
No
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-8.73 cm/s
Lipophilicity
Log Po/w (iLOGP) :
1.09
Log Po/w (XLOGP3) :
-1.56
Log Po/w (WLOGP) :
1.47
Log Po/w (MLOGP) :
-0.86
Log Po/w (SILICOS-IT) :
1.28
Consensus Log Po/w :
0.28
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-0.3
Solubility :
108.0 mg/ml ; 0.499 mol/l
Class :
Very soluble
Log S (Ali) :
0.31
Solubility :
447.0 mg/ml ; 2.06 mol/l
Class :
Highly soluble
Log S (SILICOS-IT) :
-1.86
Solubility :
3.02 mg/ml ; 0.0139 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.98
Application In Synthesis of [ 73246-30-7 ]
* 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 [ 73246-30-7 ]
1
[ 82911-69-1 ]
[ 73246-30-7 ]
[ 273221-86-6 ]
Yield Reaction Conditions Operation in experiment
95%
With sodium carbonate In 1,4-dioxane at 4 - 20℃;
With sodium carbonate In 1,4-dioxane Ambient temperature;
With sodium carbonate In 1,4-dioxane; water at 20℃;
Reference:
[1]Seyedsayamdost, Mohammad R.; Yee, Cyril S.; Reece, Steven Y.; Nocera, Daniel G.; Stubbe, JoAnne
[Journal of the American Chemical Society, 2006, vol. 128, # 5, p. 1562 - 1568]
[2]Kim, Kyonghee; Cole, Philip A.
[Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6851 - 6858]
[3]Gopishetty, Bhaskar; Ren, Lige; Waller, Tiffany M.; Wavreille, Anne-Sophie; Lopez, Miguel; Thakkar, Amit; Zhu, Jinge; Pei, Dehua
[Organic Letters, 2008, vol. 10, # 20, p. 4605 - 4608]
2
[ 28177-48-2 ]
[ 127-17-3 ]
[ 73246-30-7 ]
Yield Reaction Conditions Operation in experiment
With ammonium hydroxide; tyrosine phenollylase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol In water Ambient temperature;
With tyrosine phenol lyase; ammonia Enzymatic reaction;
With ammonium hydroxide; tyrosine phenol lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol at 20℃; Darkness; Enzymatic reaction;
Reference:
[1]Kim, Kyonghee; Cole, Philip A.
[Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6851 - 6858]
[2]Minnihan, Ellen C.; Young, Douglas D.; Schultz, Peter G.; Stubbe, Joanne
[Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15942 - 15945]
[3]Gil, Agnieszka A.; Haigney, Allison; Laptenok, Sergey P.; Brust, Richard; Lukacs, Andras; Iuliano, James N.; Jeng, Jessica; Melief, Eduard H.; Zhao, Rui-Kun; Yoon, EunBin; Clark, Ian P.; Towrie, Michael; Greetham, Gregory M.; Ng, Annabelle; Truglio, James J.; French, Jarrod B.; Meech, Stephen R.; Tonge, Peter J.
[Journal of the American Chemical Society, 2016, vol. 138, # 3, p. 926 - 935]
3
[ 28177-48-2 ]
[ 113-24-6 ]
[ 73246-30-7 ]
Yield Reaction Conditions Operation in experiment
85%
With tyrosine phenol lyase; pyridoxal 5'-phosphate; 2-hydroxyethanethiol In aq. acetate buffer at 20℃; for 96h;
50%
With tyrosine phenol-lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol In water at 20℃; for 168h;
40%
With tyrosine phenol lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol at 20℃; for 72h; Enzymatic reaction;
With ammonium acetate; tyrosine phenol lyase; 2-hydroxyethanethiol at 20℃;
Reference:
[1]Ravichandran, Kanchana R.; Liang, Li; Stubbe, Joanne; Tommos, Cecilia
[Biochemistry, 2013, vol. 52, # 49, p. 8907 - 8915]
[2]Yee, Estella F.; Dzikovski, Boris; Crane, Brian R.
[Journal of the American Chemical Society, 2019, vol. 141, # 44, p. 17571 - 17587]
[3]Yu, Yang; Lv, Xiaoxuan; Li, Jiasong; Zhou, Qing; Cui, Chang; Hosseinzadeh, Parisa; Mukherjee, Arnab; Nilges, Mark J.; Wang, Jiangyun; Lu, Yi
[Journal of the American Chemical Society, 2015, vol. 137, # 14, p. 4594 - 4597]
[4]Seyedsayamdost, Mohammad R.; Reece, Steven Y.; Nocera, Daniel G.; Stubbe, JoAnne
[Journal of the American Chemical Society, 2006, vol. 128, # 5, p. 1569 - 1579]
4
[ 73246-30-7 ]
[ 197972-08-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 10percent aq. Na2 CO3 / dioxane / Ambient temperature
5
[ 73246-30-7 ]
C34 H47 F2 N8 O20 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 10percent aq. Na2 CO3 / dioxane / Ambient temperature
3: ATP, Csk, pyruvate kinase-lactate dehydrogenase, phosphenolpyruvate, DTT, MnCl2 , Tris-HCl pH 7.4 / H2 O / 48 h / 30 °C
6
[ 28177-48-2 ]
ammonium pyruvate
[ No CAS ]
[ 73246-30-7 ]
Yield Reaction Conditions Operation in experiment
With tyrosine-phenol lyase of Citrobacter freundii; ammonium acetate at 20℃; for 336h; Darkness; Enzymatic reaction;
Reference:
[1]Gopishetty, Bhaskar; Ren, Lige; Waller, Tiffany M.; Wavreille, Anne-Sophie; Lopez, Miguel; Thakkar, Amit; Zhu, Jinge; Pei, Dehua
[Organic Letters, 2008, vol. 10, # 20, p. 4605 - 4608]
7
[ 73246-30-7 ]
[ 1437783-64-6 ]
Yield Reaction Conditions Operation in experiment
10%
With sodium hydroxide; trichlorophosphate In water at 20℃; for 1h;
Reference:
[1]Li, Fahui; Shi, Pan; Li, Jiasong; Yang, Fan; Wang, Tianyuan; Zhang, Wei; Gao, Feng; Ding, Wei; Li, Dong; Li, Juan; Xiong, Ying; Sun, Jinpeng; Gong, Weimin; Tian, Changlin; Wang, Jiangyun
[Angewandte Chemie - International Edition, 2013, vol. 52, # 14, p. 3958 - 3962][Angew. Chem., 2013, vol. 125, # 14, p. 4050 - 4054,5]
8
[ 28177-48-2 ]
[ 631-61-8 ]
[ 60-24-2 ]
[ 73246-30-7 ]
Yield Reaction Conditions Operation in experiment
With sodium pyruvate at 20 - 22℃; for 72h; Darkness; Enzymatic reaction;
Synthesis of 3,5-difluorotyrosine
To synthesize F2-Tyr, we transformed2,6-difluorophenol to F2-Tyr by using Citrobacter freundii (ATCC8090)tyrosine phenol lyase (TPL) following established methods 46. One liter solution containing 30 mM ammonium acetate, 60 mM sodium pyruvate, 5 mMβ -mercaptoethanol, 40 μ M PLP, and 10 mg of TPL enzyme, pH 8.0, was stirred in the dark for 3 d at room temperature (20-22 °C). The aqueous phase wasthen concentrated and purified by a C-18 column from 10% to 90% methanol,0.1% trifluoroacetic acid (v/v) in water.
Reference:
[1]Li, Jiasong; Griffith, Wendell P.; Davis, Ian; Shin, Inchul; Wang, Jiangyun; Li, Fahui; Wang, Yifan; Wherritt, Daniel J.; Liu, Aimin
[Nature Chemical Biology, 2018, vol. 14, # 9, p. 853 - 860]
9
[ 24424-99-5 ]
[ 73246-30-7 ]
(S)-2-((tert-butoxycarbonyl)amino)-3-(3,5-difluoro-4-hydroxyphenyl)propanoic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
84.4%
With sodium hydrogencarbonate In water; acetonitrile at 0 - 20℃; for 12h;
Step-01: Sodium (S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate (29)
To an ovendried 10-mL round-bottomed flask under N2 was added t-BuOH (15 mL), (S)-2-amino-3-(pyridin-2-yl)propanoic acid (28) (400 mg, 2.407 mmol), BOC2O (0.671 mL, 2.89 mmol) and NaOH (212 mg, 5.30 mmol) and Water (7 mL). The reaction mixture was stirred for 2h at rt. after 2h the mixture was concentrated at room temperature to dryness under reduced pressure to produce white solids of sodium (S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate (29) (690 mg, 2.394 mmol, 99 % yield). MS (ESI): 267.2 as [M+H]+ in +Ve mode.
10
[ 73246-30-7 ]
cyanomethyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3,5-difluoro-4-hydroxyphenyl)propanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / water; acetonitrile / 12 h / 0 - 20 °C
2: triethylamine / N,N-dimethyl-formamide / 12 h / 0 °C
11
[ 73246-30-7 ]
(14) cyanomethyl (S)-2-amino-3-(3,5-difluoro-4-hydroxyphenyl) propanoate hydrochloride
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate / water; acetonitrile / 12 h / 0 - 20 °C
2: triethylamine / N,N-dimethyl-formamide / 12 h / 0 °C
3: hydrogenchloride / 1,4-dioxane; acetonitrile / 2 h / 0 - 15 °C / Inert atmosphere
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