[ CAS No. 475250-52-3 ] {[proInfo.proName]}

Name: 475250-52-3|2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|97%
Brand: Ambeed
SKU: A826381
Price: 13.0 USD
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2D 3D

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Quality Control of [ 475250-52-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 475250-52-3 ]

SDS Specification

Alternatived Products of [ 475250-52-3 ]

Product Details of [ 475250-52-3 ]

CAS No. :	475250-52-3	MDL No. :	MFCD10698526
Formula :	C₁₄H₂₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HPNLRRQVSZVKHY-UHFFFAOYSA-N
M.W :	248.13	Pubchem ID :	12012759
Synonyms :

Calculated chemistry of [ 475250-52-3 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	73.68
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.17
Log Po/w (WLOGP) :	2.87
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	1.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.0934 mg/ml ; 0.000377 mol/l
Class :	Soluble
Log S (Ali) :	-3.42
Solubility :	0.0939 mg/ml ; 0.000378 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.53
Solubility :	0.00726 mg/ml ; 0.0000292 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 475250-52-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 475250-52-3 ]

* 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 [ 475250-52-3 ]

[ 475250-52-3 ] Synthesis Path-Downstream 1~88

1
[ 70744-47-7 ]
[ 166330-03-6 ]
[ 475250-52-3 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 5647 - 5650

2
[ 824-94-2 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris(2,4-pentanedionato)iron(III); magnesium; In tetrahydrofuran; at -10℃; for 8h;Inert atmosphere;	Example 3: Under the conditions of adding magnesium turnings in situ,The boron esterification of p-methoxybenzyl chloride with pinacol diboron catalyzed by Fe(acac)3 was carried out by adding the catalyst (3.5 mg, 0.010 mmol, 2 mol%) in order under argon protection.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol),Tetrahydrofuran (1 ml) with p-methoxybenzyl chloride added at -10C183 μl, 1.35 mmol), the reaction was carried out for 8 hours, and the reaction was terminated with the addition of water.The ester was extracted and the yield calculated by gas chromatography was 90%.
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate; In 1,4-dioxane; for 18h;Inert atmosphere; Reflux;	Preparation of 2b is representative. A two-necked round-bottomed flask containing 2.07 g (15 mmol) of K2CO3, 1.52 g (6.0 mmol) of bis(pinacolato)diboron and 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium was equipped with a reflux condenser, filled with nitrogen, and charged with dry 1,4-dioxane (30 mL) and 0.78 g of 4-methoxybenzyl chloride 5b (5.0 mmol). The mixture was refluxed with stirring for 18 h, and then the insoluble materials were filtered off after cooling. The filtrate was condensed under reduced pressure to give the crude benzylboron 6b, which was purified by short column chromatography on silica gel using hexane/ethyl acetate (9/1) as an eluent. The above product (0.79 g, 3.2 mmol) was dissolved in 8 mL of methanol. An aqueous solution (4 mL) of KHF2 (1.5 g, 19 mmol) was added drop-by-drop with vigorous stirring, and then the mixture was stirred for 24 h at room temperature. The solvents were removed under reduced pressure below 60 C to give a solid residue, which was suspended in hot acetone, stirred vigorously, and filtered with suction to extract the benzyltrifluoroborate. This treatment was repeated two more times. The combined filtrate was evaporated, and the residue was recrystallized from acetonitrile/ether to afford pure 2b in 56 % yield (0.41 g, 1.8 mmol).[i] 1H NMR (CD3CN): 6.98-6.68 (m, 4H, ArH), 3.70 (s, 3H, OCH3), 1.47 (br s, 2H, CH2Ar). [i] (a) P. Jain, S. Yi, P. T. Flaherty, J. Heterocycl. Chem. 2013, 50, E166. (b) J. C. Tellis, D. N. Primer, G. A. Molander, Science 2014, 345, 433.

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 233 - 235
[2]Patent: CN107903281,2018,A .Location in patent: Paragraph 0022
[3]Organic Letters,2022,vol. 24,p. 2931 - 2934
[4]Chemistry Letters,2002,p. 780 - 781
[5]Journal of the American Chemical Society,2014,vol. 136,p. 9521 - 9523
[6]Chemistry Letters,2002,p. 780 - 781
[7]Chemistry Letters,2020,vol. 49,p. 118 - 120

3
[ 824-94-2 ]
[ 25015-63-8 ]
[ 475250-52-3 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 8031 - 8033
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827
[3]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827

4
[ 104-93-8 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 6Zr(4+)6C20H12O4(2-)8O(2-)4Cl(1-)4Co(2+); sodium triethylborohydride; In n-heptane; at 103℃; for 60h;Schlenk technique; Inert atmosphere; Glovebox;	General procedure: In a glovebox, UiO-68-MOF-CoCl (1.0 mg, 0.2 mol % Co) was charged into a small vial and 0.5 mL THF was added. Then, 15 μL NaBEt3H (1.0 M in THF) was added to the vial and the mixture was stirred slowly for 1 h in the glovebox. The solid was centrifuged out of suspension and washed with THF two times and with heptane two times. B2pin2 (43.0 mg, 0.169 mmol) and p-xylene (41.8 μL, 0.34 mmol) in 2.0 mL heptane was added to the vial and the resultant mixture was transferred to a Schlenk tube. The tube was heated under nitrogen at 103 C. for 2.5 d to obtain the alkyl boronate ester in 94% yield as determined by GC analysis. Upon treatment of NaEt3BH, UiO-68-Co became an active catalyst for undirected dehydrogenative borylation of benzylic C-H bonds using B2(pin)2 (pin=pinacolate) or HBpin as the borylating agents. Borylation of alkyl C-H bonds provides alkyl boronates, which are versatile reagents in organic synthesis. The UiO-68-Co catalyzed borylation reactions were first screened for optimized conditions such as temperature, solvents, and in neat arenes (without using a solvent) to obtain better results. The screening experiments revealed that high turnover frequencies as well as regioselectivities were observed when the borylation reactions were performed using B2(pin)2 in neat arene or refluxed in n-heptane for solid substrates at 103 C. See Table 1, below. The catalytic activity and regioselectivity of UiO-68-Co was higher compared to those of analogous UiO-MOFs having smaller pore sizes such as UiO-67-Co and UiO-66-Co. See Table 2, below. Under optimized reaction conditions, primary benzylic boronate esters were afforded in excellent yields from a range of methylarenes with 0.2 mol % UiO-68-Co. See Table 1. Impressively, UiO-68-Co catalyzed borylation occurred not only at primary benzylic C-H bonds, but also at secondary and tertiary benzylic C-H bonds. See entries 12 and 13, Table 1.

Reference： [1]Chemistry Letters,2001,p. 1082 - 1083
[2]Patent: US2018/361370,2018,A1 .Location in patent: Paragraph 0238; 0243
[3]Angewandte Chemie - International Edition,2022,vol. 61
Angew. Chem.,2022,vol. 134

5
[ 2746-25-0 ]
[ 25015-63-8 ]
[ 475250-52-3 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827

6
[ 104-92-7 ]
[ 78782-17-9 ]
[ 475250-52-3 ]

Reference： [1]Chemistry Letters,2013,vol. 42,p. 1363 - 1365
[2]Organic Letters,2011,vol. 13,p. 3368 - 3371

7
[ 100-61-8 ]
[ 475250-52-3 ]
[ 37931-52-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1544 - 1547

8
[ 475250-52-3 ]
[ 74-88-4 ]
[ 1515-95-3 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 9391 - 9401

9
[ 37675-31-3 ]
[ 475250-52-3 ]
[ 42238-20-0 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 9526 - 9531

10
[ 40775-69-7 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600

11
[ 911847-39-7 ]
[ 475250-52-3 ]
C₂₂H₂₇NO₄ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2726 - 2744

12
C₂₂H₃₈O₃Sn [ No CAS ]
[ 475250-52-3 ]
(R)-2-(1-(4-methoxyphenyl)propan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 4398 - 4403

13
[ 104-93-8 ]
[ 745783-97-5 ]
[ 475250-52-3 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 8633 - 8643

14
[ 73183-34-3 ]
[ 475250-52-3 ]

Reference： [1]Journal of the American Chemical Society,2022,vol. 144,p. 2460 - 2467
[2]Journal of the American Chemical Society,2015,vol. 137,p. 8633 - 8643

15
[ 104-93-8 ]
[ 73183-34-3 ]
[ 123-11-5 ]
[ 475250-52-3 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 766 - 769

16
[ 66107-29-7 ]
[ 78782-17-9 ]
[ 475250-52-3 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 51932 - 51935

17
[ 105-13-5 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Reference： [1]ACS Catalysis,2021,vol. 11,p. 758 - 766
[2]Organic Letters,2017,vol. 19,p. 1204 - 1207

18
[ 76-09-5 ]
[ 5720-07-0 ]
[ 18107-18-1 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
71%		To a 10 mL reaction tube equipped with a magnet, 0.4 mL (0.8 mmol) of trimethylsilyl diazomethane (2M n-hexane solution) was added to a solution of 1 mL of 4-methoxybenzeneboronic acid (0.4 mmol) 1,4-dioxane, plug the rubber stopper and react for 5 hours at 60 C on an electromagnetic heating stirrer.Followed by the addition of 71 mg (0.6 mmol) of pinacol (dissolved in 1 mL of 1,4-dioxane), 0.6 mL of tetrabutylammonium fluoride (1 M solution in tetrahydrofuran) and 200 uL of water at 60 C in an electromagnetic heating stirrer Continue to react for 5 hours.After the completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography to give 4-methoxybenzylboronic acid pinacol ester, whose structure was as follows:The compound was a colorless liquid in a yield of 71% and its NMR data were as follows:

Reference： [1]Patent: CN105884808,2016,A .Location in patent: Paragraph 0058; 0059; 0060; 0061; 0062; 0063
[2]Chemical Science,2017,vol. 8,p. 6071 - 6075

19
[ 15260-65-8 ]
[ 475250-52-3 ]
2-(3-(4-methoxyphenyl)-1-phenylpropyl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

20
[ 1663-39-4 ]
[ 475250-52-3 ]
tert-butyl 4-(4-methoxyphenyl)butanoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

21
[ 2495-35-4 ]
[ 475250-52-3 ]
benzyl 4-(4-methoxyphenyl)butanoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

22
[ 78-94-4 ]
[ 475250-52-3 ]
[ 66265-99-4 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5
[2]Chemical Communications,2018,vol. 54,p. 5606 - 5609

23
[ 107-02-8 ]
[ 475250-52-3 ]
[ 56047-51-9 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

24
[ 107-13-1 ]
[ 475250-52-3 ]
[ 72457-25-1 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

25
[ 5535-48-8 ]
[ 475250-52-3 ]
1-methoxy-4-(3-(phenylsulfonyl)propyl)benzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

26
[ 292638-85-8 ]
[ 475250-52-3 ]
[ 20637-08-5 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

27
[ 80-62-6 ]
[ 475250-52-3 ]
4-(4-methoxyphenyl)-2-methylbutyric acid methyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

28
[ 547-65-9 ]
[ 475250-52-3 ]
3-(4-methoxyphenethyl) dihydrofuran-2(3H)-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

29
[ 930-30-3 ]
[ 475250-52-3 ]
2-(4-methoxybenzyl)cyclopentanone [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

30
[ 930-68-7 ]
[ 475250-52-3 ]
[ 898785-44-9 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

31
[ 623-91-6 ]
[ 475250-52-3 ]
diethyl 2-(4-methoxybenzyl)succinate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

32
[ 100-43-6 ]
[ 475250-52-3 ]
[ 56753-75-4 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

33
[ 100-69-6 ]
[ 475250-52-3 ]
2-(3-(4-methoxyphenyl)propyl)pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

34
[ 653-34-9 ]
[ 475250-52-3 ]
[ 1616842-32-0 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

35
[ 491-38-3 ]
[ 475250-52-3 ]
[ 84289-40-7 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

36
[ 574-12-9 ]
[ 475250-52-3 ]
3-(4-methoxybenzyl)-2-phenylchroman-4-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 15136 - 15140
Angew. Chem.,2017,vol. 129,p. 15332 - 15336,5

37
[ 2746-25-0 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
5 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 12h;	A solution of l-(bromomethyl)-4-methoxybenzene (6 g, 30 mmol) in degassed 1,4- dioxane (50 mL) was treated with bis(pinacolato)diboron (11.4 g, 45 mmol), potassium acetate (8.8 g, 90 mmol), Pd(dppf)Cl2 (1.02 g, 1.4 mmol) and the mixture heated at 100 C for 12 h. The mixture was cooled to rt and filtered. Filtrate was concentrated and the crude was purified by column chromatography on silica gel, eluting with 5% of ethyl acetate in petroleum ether to afford 2-(4-memoxybenzyl)-4,4,5,5-tetramethyl- ,3,2-dioxaborolane (5 g, 60%) as a colorless oil.

Reference： [1]Organic Letters,2018,vol. 20,p. 4979 - 4983
[2]Patent: WO2018/136401,2018,A1 .Location in patent: Paragraph 0365
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 7160 - 7184

38
[ 475250-52-3 ]
[ 105-13-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4979 - 4983

39
methyl 4-benzyloxy-1-methyl-7-bromoisoquinoline-3-carboxylate [ No CAS ]
[ 475250-52-3 ]
methyl 4-(benzyloxy)-7-(4-methoxybenzyl)-1-methylisoquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	Compound 29a (300 mg, 0.78 mmol), p-methoxybenzylboronic acid pinacol ester (386 mg, 1.56 mmol), NaHCO3 (164 mg, 1.95 mmol), DMF (4 mL), H2O (1 mL) After nitrogen substitution, Pd(dppf)Cl2 (85 mg, 0.15 mmol) was added.After nitrogen substitution, the temperature was raised to 90 C, and TLC was monitored until the reaction of the crude material was complete. After cooling to room temperature, the reaction solution was poured into water.The title compound 29b (180 mg, 41%) was obtained.

Reference： [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0436-0439

40
methyl 4-benzyloxy-1-methyl-7-bromoisoquinoline-3-carboxylate [ No CAS ]
[ 475250-52-3 ]
4-hydroxy-7-(4-methoxybenzyl)-1-methylisoquinoline-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With palladium diacetate; potassium carbonate; catacxium A; In water; N,N-dimethyl-formamide; at 90℃; for 12h;Inert atmosphere;	<strong>[475250-52-3]4-methoxybenzylboronic acid pinacol ester</strong> (650 mg, 2.6 mmol), 4-(benzyloxy)-7-bromo-1-methylisoquineMethyl -3-carboxylate (500 mg, 1.3 mmol), Pd(OAc) 2 (70 mg, 0.3 mmol), CataCXium A (170 mg, 0.5 mmol), K2CO3 (360 mg, 2.6 mmol) and DMF/water (15 mL/3 mL) The solution was sequentially added to a 100 mL reaction flask, and the reaction solution was replaced with nitrogen three times and then heated to 90 C for 12 h, and TLC was monitored until the starting material was completely reacted. The reaction solution was poured into 60 mL of water and quenched, extracted with EA (40 mL×3) to remove impurities and then adjusted to pH 5 with HCl (3 N). The precipitated solid was collected by filtration. The title compound 36c (100 mg, 26%) was obtained.

Reference： [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0508-0511

41
[ 18680-27-8 ]
[ 475250-52-3 ]
[ 243145-80-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	In diethyl ether; at 20℃;	A solution of (l S,2S,3 ,5S)-2,6,6-irimeihylbicyclo[3.1.1]heptane-2,3-diol (4.9 g, 28.8 mmol) in diethyl ether (100 mL) was treated with 2-(4-niethoxybenzyl)-4,4,5,5~tetramethyl-l,3,2- dioxaborolane (5 g, 20 mmol), the mixture was stirred at rt for 12 h. Then the mixture was concentrated and the crude was purified by column chromatography on silica gel, eluting with 5% of ethyl acetate in petroleum ether to afford the (3aS,4S,6S,7aR)-2-(4-methoxybenzyl)-3a,5,5-irimethylhexaliydro-4,6- methanobenzo[d] \| 1,3,2 jdioxaborole (4.5 g, 75%) as a colorless oil.

Reference： [1]Patent: WO2018/136401,2018,A1 .Location in patent: Paragraph 0366
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 7160 - 7184

42
[ 76-09-5 ]
[ 13826-27-2 ]
[ 71017-75-9 ]
[ 475250-52-3 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8572 - 8576
Angew. Chem.,2019,vol. 131,p. 8660 - 8664,5
[2]Chemistry - A European Journal,2018,vol. 24,p. 17210 - 17214

43
[ 254454-54-1 ]
[ 475250-52-3 ]
tert-butyl 2-(4-methoxybenzyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With dichloro(1,5-cyclooctadiene)palladium(II); tetrabutylammomium bromide; caesium carbonate; ruphos; In 1,4-dioxane; water; at 80℃; for 24h;Inert atmosphere;	General procedure: General Procedure: A glass test tube, which was equipped with a magnetic stir bar and fitted with a stopper, was charged with Pd(COD)Cl2 (14.3 mg, 0.05 mmol) and RuPhos (46.7 mg, 0.10 mmol). Cs2CO3 (488.7 mg, 1.5 mmol, 3.0 equiv.), benzylboronic acid pinacol ester (1.0 mmol, 2.0 equiv.), N-Boc-3-iodo-azetidine (283.1 mg, 0.5 mmol, 1.0 equiv.) and 3 mL 1,4-dioxane/H2O (1:1). The reaction mixture was purged with argon gas three times. Under argon, the reaction mixture was allowed to stir at 80 oC for 24 h. The progress of the reaction was monitored by GC-MS. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (15 mL) and washed with saturated brine (3×10 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over MgSO4, concentrated in vacuo, and purified by silica gel flash chromatography.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1321 - 1324

44
[ 100-39-0 ]
[ 73183-34-3 ]
[ 103-29-7 ]
[ 475250-52-3 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 8872 - 8876
Angew. Chem.,2019,vol. 131,p. 8964 - 8968,5

45
[ 76-09-5 ]
[ 13826-27-2 ]
4-methoxybenzyl methyl oxalate [ No CAS ]
[ 475250-52-3 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9561 - 9564
Angew. Chem.,2019,vol. 131,p. 9661 - 9665,5

46
[ 91-02-1 ]
[ 475250-52-3 ]
2-(4-methoxyphenyl)-1-phenyl-1-(pyridin-2-yl)ethan-1-ol [ No CAS ]