Alternatived Products of [ 851231-30-6 ]
Product Details of [ 851231-30-6 ]
CAS No. : 851231-30-6
MDL No. : MFCD22494601
Formula :
C14 H21 BO4
Boiling Point :
-
Linear Structure Formula : -
InChI Key : FZSMHXDGONFVOO-UHFFFAOYSA-N
M.W :
264.13
Pubchem ID : 12192578
Synonyms :
Calculated chemistry of [ 851231-30-6 ]
Physicochemical Properties
Num. heavy atoms :
19
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.57
Num. rotatable bonds :
3
Num. H-bond acceptors :
4.0
Num. H-bond donors :
0.0
Molar Refractivity :
75.9
TPSA :
36.92 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
Yes
CYP1A2 inhibitor :
No
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-5.89 cm/s
Lipophilicity
Log Po/w (iLOGP) :
0.0
Log Po/w (XLOGP3) :
2.85
Log Po/w (WLOGP) :
2.0
Log Po/w (MLOGP) :
1.08
Log Po/w (SILICOS-IT) :
1.9
Consensus Log Po/w :
1.57
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-3.31
Solubility :
0.13 mg/ml ; 0.000491 mol/l
Class :
Soluble
Log S (Ali) :
-3.28
Solubility :
0.137 mg/ml ; 0.00052 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-4.25
Solubility :
0.0147 mg/ml ; 0.0000557 mol/l
Class :
Moderately soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
1.0 alert
Leadlikeness :
0.0
Synthetic accessibility :
3.21
Safety of [ 851231-30-6 ]
Application In Synthesis of [ 851231-30-6 ]
* 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 [ 851231-30-6 ]
Downstream synthetic route of [ 851231-30-6 ]
1
[ 851231-30-6 ]
[ 16932-45-9 ]
2
[ 25240-59-9 ]
[ 60319-07-5 ]
[ 851231-30-6 ]
Yield Reaction Conditions Operation in experiment
93%
With triethylamine In 1,4-dioxane Heating;
3
[ 851231-30-6 ]
[ 591-18-4 ]
[ 106384-87-6 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran Heating;
4
[ 851231-30-6 ]
[ 615-42-9 ]
2'-Iodo-2,6-dimethoxy-1,1'-biphenyl
[ No CAS ]
Yield Reaction Conditions Operation in experiment
70%
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
5
[ 851231-30-6 ]
[ 108-36-1 ]
[ 106384-87-6 ]
3-bromo-2',6'-dimethoxybiphenyl
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran Heating;
6
[ 851231-30-6 ]
[ 626-00-6 ]
[ 106384-87-6 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
7
[ 851231-30-6 ]
[ 626-00-6 ]
2,6-dimethoxy-3'-iodobiphenyl
[ No CAS ]
[ 106384-87-6 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
8
[ 851231-30-6 ]
[ 106-37-6 ]
[ 121968-94-3 ]
[ 168849-77-2 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran Heating;
9
[ 851231-30-6 ]
[ 589-87-7 ]
[ 121968-94-3 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran Heating;
10
[ 851231-30-6 ]
[ 624-38-4 ]
[ 121968-94-3 ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
11
[ 851231-30-6 ]
[ 624-38-4 ]
2,6-dimethoxy-4'-iodobiphenyl
[ No CAS ]
[ 121968-94-3 ]
Yield Reaction Conditions Operation in experiment
1: 30%
2: 56%
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
12
[ 851231-30-6 ]
[ 626-44-8 ]
3,5-diiodo-2',6'-dimethoxybiphenyl
[ No CAS ]
5'-iodo-2,2'',6,6''-tetramethoxy-1,1':3',1''-terphenyl
[ No CAS ]
5'-(2,6-dimethoxyphenyl)-2,2'',6,6''-tetramethoxy-1,1':3',1''-terphenyl
[ No CAS ]
13
[ 851231-30-6 ]
[ 3001-15-8 ]
2,6-dimethoxy-4''-iodo-1,1':4',1''-terphenyl
[ No CAS ]
2,2''',6,6'''-tetramethoxy-1,1':4',1'':4'',1'''-quaterphenyl
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With tetrakis(triphenylphosphine) palladium(0) ; silver carbonate In tetrahydrofuran for 18h; Heating;
14
[ 91-10-1 ]
[ 851231-30-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 98 percent / pyridine / CH2 Cl2 / 0.25 h / 0 °C
2: 93 percent / Et3 N / PdCl2 (dppf) / dioxane / Heating
15
[ 851231-30-6 ]
[ 70654-65-8 ]
[ 1220498-60-1 ]
Yield Reaction Conditions Operation in experiment
91%
Stage #1: 1‐tetrahydropyran‐2’‐yloxy‐4‐bromonaphthalene With sodium carbonate In 1,2-dimethoxyethane; water Inert atmosphere;
Stage #2: 1,3-dimethoxy-2-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolanyl)-benzene With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 4h; Inert atmosphere;
16
[ 61676-62-8 ]
[ 16932-45-9 ]
[ 851231-30-6 ]
17
[ 851231-30-6 ]
[ 100-39-0 ]
[ 93961-29-6 ]
[ 1334531-99-5 ]
Yield Reaction Conditions Operation in experiment
15 %Spectr.
With [Rh(OH)(cod)]2; potassium <i>tert</i>-butylate In tert-butyl methyl ether at 20 - 40℃; for 4h; Inert atmosphere;
18
[ 76-09-5 ]
[ 23112-96-1 ]
[ 851231-30-6 ]
Yield Reaction Conditions Operation in experiment
100%
In tetrahydrofuran at 60 - 70℃; for 4h; Inert atmosphere;
3 Preparation of Compound III
30.9g (0.17mol) compound II, 100.3g(0.85mol) pinacol (systematic name is 2,3-dimethyl-2,3-butanediol), 180g of tetrahydrofuran into 500ml three-necked flask. The system under a nitrogen atmosphere, 60 ~ 70 deg.C reaction stirred 4h. After maintaining temperature, measured by gas chromatographic purity of 99.5%, a yield of 100% was recorded.
98%
In toluene for 15h; Reflux; Dean-Stark;
In diethyl ether at 20℃; for 18h; Inert atmosphere;
Reference:
[1]Current Patent Assignee: VALIANT CO., LTD. - CN105348240, 2016, A
Location in patent: Paragraph 0061; 0062
[2]Ra, Doyoung; Gauger, Kelly A.; Muthukumaran, Kannan; Balasubramanian, Thiagarajan; Chandrashaker, Vanampally; Taniguchi, Masahiko; Yu, Zhanqian; Talley, Daniel C.; Ehudin, Melanie; Ptaszek, Marcin; Lindsey, Jonathan S.
[Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 4, p. 547 - 572]
[3]Ling, Liang; He, Yuan; Zhang, Xue; Luo, Meiming; Zeng, Xiaoming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 20, p. 6554 - 6558][Angew. Chem., 2019, vol. 131, # 20, p. 6626 - 6630,5]
19
[ 851231-30-6 ]
[ 95-56-7 ]
2',6'-dimethoxy-(1,1'-biphenyl)-2-ol
[ No CAS ]
Yield Reaction Conditions Operation in experiment
90%
With tetrakis(triphenylphosphine) palladium(0) ; sodium carbonate In tetrahydrofuran; water at 60 - 70℃; for 3h; Inert atmosphere;
3 Preparation of Example IV
44.9g (0.167mol) compound III in tetrahydrofuran solution, 90.9g (0.51mol) o-bromophenol, 0.38 g (0.00034 mol) of tetrakis (triphenylphosphine) palladium, 36.0 g (0.34 mol) of sodium carbonate, 265g of water, under a nitrogen atmosphere, 60 ~ 70 deg.C stir and maintain temperature for 3h. Completion of the reaction,200g of toluene was added to the system, stirred for 10min, layers were separated the organic phase washed with water until neutral, the organic phase solvent under reduced pressure, the resulting product was added to petroleum ether to give 31g white powder, yield 90%, measured by gas chromatographic purity of 99.2%.
20
[ 851231-30-6 ]
[ 33483-06-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0) ; sodium carbonate / tetrahydrofuran; water / 3 h / 60 - 70 °C / Inert atmosphere
2: pyridine hydrochloride / 3 h / 180 - 200 °C / Inert atmosphere
3: toluene-4-sulfonic acid / 1,2-dichloro-benzene / 4 h / 140 - 160 °C / Inert atmosphere
21
[ 851231-30-6 ]
[ 1419872-20-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) ; sodium carbonate / tetrahydrofuran; water / 3 h / 60 - 70 °C / Inert atmosphere
2: pyridine hydrochloride / 3 h / 180 - 200 °C / Inert atmosphere
22
[ 151-10-0 ]
[ 851231-30-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -40 - 30 °C / Inert atmosphere
1.2: 1 h / -40 - -30 °C
1.3: 1 h / 20 - 30 °C
2.1: tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
23
[ 851231-30-6 ]
[ 3964-04-3 ]
C17 H15 NO2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
76%
With potassium phosphate monohydrate; (PCy<SUB>3</SUB>)Pd(crotyl)Cl; FI-750-M In water at 65℃; Inert atmosphere; Micellar solution; Green chemistry;
24
[ 851231-30-6 ]
2-(2,6-dimethoxycyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
[ No CAS ]
Yield Reaction Conditions Operation in experiment
61%
With [Rh(cod)(CI)(CAACMe2 )]; hydrogen In 2,2,2-trifluoroethanol at 40℃; for 24h; Autoclave; Molecular sieve; stereoselective reaction;
Reference:
[1]Ling, Liang; He, Yuan; Zhang, Xue; Luo, Meiming; Zeng, Xiaoming
[Angewandte Chemie - International Edition, 2019, vol. 58, # 20, p. 6554 - 6558][Angew. Chem., 2019, vol. 131, # 20, p. 6626 - 6630,5]
25
[ 16932-45-9 ]
[ 73183-34-3 ]
[ 851231-30-6 ]
Yield Reaction Conditions Operation in experiment
75%
With tris(4-methoxy-3,5-bis-dimethylphenyl)phosphine; palladium diacetate; caesium carbonate In ethyl acetate at 80℃; for 24h; Sealed tube;
26
[ 851231-30-6 ]
CsPbBr3
[ No CAS ]
C14 H20 BBrO4
[ No CAS ]
Yield Reaction Conditions Operation in experiment
43 %Spectr.
With N-ethyl-N,N-diisopropylamine; 1,1-dibromomethane Irradiation;
Reference:
[1]Deng, Zhijie; Huang, Yanmin; Li, Yonglong; Wang, Teng; Wang, Ying; Xie, Wei; Yuan, Mingjian; Zhang, Cancan; Zhang, Li; Zhu, Aonan
[ACS Catalysis, 2022, p. 5903 - 5910]