[ CAS No. 953075-90-6 ] {[proInfo.proName]}

Name: 953075-90-6|(2,6-Diethyl-4-methylphenyl)boronic acid|97%
Brand: Ambeed
SKU: A1142356
Rating: 90 (27 reviews)

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2D 3D

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Quality Control of [ 953075-90-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 953075-90-6 ]

SDS Specification

Alternatived Products of [ 953075-90-6 ]

Product Details of [ 953075-90-6 ]

CAS No. :	953075-90-6	MDL No. :	MFCD25563305
Formula :	C₁₁H₁₇BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RJIQZLJNCMHCCN-UHFFFAOYSA-N
M.W :	192.06	Pubchem ID :	57437319
Synonyms :

Calculated chemistry of [ 953075-90-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	60.78
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.78
Log Po/w (WLOGP) :	0.8
Log Po/w (MLOGP) :	1.86
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	1.36

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.9
Solubility :	0.241 mg/ml ; 0.00126 mol/l
Class :	Soluble
Log S (Ali) :	-3.29
Solubility :	0.0995 mg/ml ; 0.000518 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.105 mg/ml ; 0.000547 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 953075-90-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 953075-90-6 ]

* 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.

Downstream synthetic route of [ 953075-90-6 ]

[ 953075-90-6 ] Synthesis Path-Downstream 1~69

2
[ 121-43-7 ]
[ 314084-61-2 ]
[ 953075-90-6 ]

Yield	Reaction Conditions	Operation in experiment
78%		To a solution at -78C of 25g (110 mmol) of <strong>[314084-61-2]2,6-diethyl-4-methylbromobenzene</strong> (preparation described in WO 2000078712) in 240 ml of tetrahydrofuran is added a -1.6 M solution of butyllithium in hexanes (75 ml, 120 mmol) dropwise over 10 minutes. The mixture is stirred for 10 minutes at -78cC, then trimethylborate (24.6 ml, 22.9g; 220 mmol) is added at once and stirring is continued at -780C for 30 minutes. The cooling bath is removed and the solution is allowed to warm up to room temperature over 1 hour and quenched with 2N aqueous hydrochloric acid (140 ml).The organic layer is separated, and the aqueous phase is extracted three times with diethyl ether : hexane 1 :1. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The oily residue is taken up in hexane under stirring, and the white solid is collected by filtration to give 2,6-diethyl-4-methylphenylboronic acid. The filtrate is concentrated and purified by column chromatography on silica gel give a further quantity of desired product. A combined yield of 16.6g (78%) of 2,6-diethyl-4-methylphenylboronic acid is obtained.

Reference： [1]Patent: WO2008/110307,2008,A1 .Location in patent: Page/Page column 69

3
[ 953075-90-6 ]
[ 1057654-41-7 ]
2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; tetrabutylammomium bromide;palladium diacetate; In 1,2-dimethoxyethane; water; at 50℃; for 5.75h;	A portion of the ylide (0.70 g, 1.76 mmol) prepared in step 5, <strong>[953075-90-6]2,6-diethyl-4-methylphenylboronic acid</strong> (0.372 g, 1.93 mmol), palladium acetate (0.02 g, 0.09 mmol), tetrabutylammonium bromide (0.583 g , 1.76 mmol) and lithium hydroxide monohydrate (0.222 g, 5.28 mmol) are added to a mixture of 1 ,2-dimethoxyethane (20 ml) and water (5 ml) and the mixture is heated at 50 0C for 5 3A hours. The mixture is cooled to room temperature, filtered through diatomaceous earth to remove the catalyst, and the filtrate is partitioned between ethyl acetate and water. The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 2-(2,6-diethyl-4-methylphenyl)-5- (tetrahydropyran-4-yl)cyclohexane-1 ,3-dione.1 H NMR data (CDCI3, ppm): deltaH 6.98 (s, 2H), 5.54 (br s, 1 H), 4.04 (d, 2H), 3.40 (t, 2H), 2.71 - 2.64 (m, 2H), 2.47 - 2.23 (m, 9H), 2.11 - 2.00 (m, 1 H), 1.72 - 1.69 (m, 2H), 1.60 (m, 1 H), 1.50 - 1.35 (m, 2H), 1.08 (m, 6H)

Reference： [1]Patent: WO2008/110307,2008,A1 .Location in patent: Page/Page column 39

4
[ 953075-90-6 ]
C₁₆H₁₇IO₃ [ No CAS ]
2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydrofuran-3-yl)cyclohexane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; tetrabutylammomium bromide;palladium diacetate; In 1,2-dimethoxyethane; water; at 50℃; for 5.75h;	A portion of the ylide (0.85 g, 2.21 mmol), <strong>[953075-90-6]2,6-diethyl-4-methylphenylboronic acid</strong> (0.467 g, 2.43 mmol), palladium acetate (0.025 g, 0.11 mmol), tetrabutylammonium bromide (0.734 g , 2.21 mmol) and lithium hydroxide monohydrate (0.278 g, 6.63 mmol) are added to a mixture of 1 ,2- dimethoxyethane (24 ml) and water (6 ml) and the mixture is heated at 50 0C for 5 3A hours. The mixture is cooled to room temperature, filtered through diatomaceous earth to remove the catalyst, and the filtrate is partitioned between ethyl acetate and water. The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydrofuran-3- yl)cyclohexane-1 ,3-dione.1 H NMR data (CDCI3, ppm): deltaH 6.94 (s, 2H), 3.93-3.89 (t, 1 H), 3.87-3.83 (m, 1 H), 3.76-3.70 (q, 1 H), 3.44-3.39 (t, 1 H), 2.64-2.62 (m, 1 H), 2.53-2.48 (m, 1 H), 2.28 (s, 3H), 2.34-2.24 (m, 6H), 2.21-2.12 (m, 1 H), 2.11-1.99 (m, 2H), 1.65-1.55 (m, 1 H), 1.05-1.01 (m, 6H)

Reference： [1]Patent: WO2008/110307,2008,A1 .Location in patent: Page/Page column 40-41

5
[ 314084-61-2 ]
[ 953075-90-6 ]

Yield	Reaction Conditions	Operation in experiment
78%		Example 1APreparation of 2,6-diethyl-4-methylphenylboronic acidTo a solution at -78C of 25g (110 mmol) of <strong>[314084-61-2]2,6-diethyl-4-methylbromobenzene</strong> (preparation described in WO 2000078712) in 240 ml of tetrahydrofuran is added a -1.6 M solution of butyllithium in hexanes (75 ml, 120 mmol) dropwise over 10 minutes. The mixture is stirred for 10 minutes at -78C, then trimethylborate (24.6 ml, 22.9g; 220 mmol) is added at once and stirring is continued at -78C for 30 minutes. The cooling bath is removed and the solution is allowed to warm up to room temperature over 1 hour and quenched with 2N aqueous hydrochloric acid (140 ml).The organic layer is separated, and the aqueous phase is extracted three times with diethyl ether : hexane 1 :1. The organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The oily residue is taken up in hexane under stirring, and <n="168"/>the white solid is collected by filtration to give 2,6-diethyl-4-methylphenylboronic acid. The filtrate is concentrated and purified by column chromatography on silica gel give a further quantity of desired product. A combined yield of 16.6g (78%) of 2,6-diethyl-4-methylphenylboronic acid is obtained.

Reference： [1]Patent: WO2008/110308,2008,A2 .Location in patent: Page/Page column 166

6
[ 953075-90-6 ]
[ 1058731-67-1 ]
[ 1068095-37-3 ]

Yield	Reaction Conditions	Operation in experiment
		The reaction mixture is diluted with 1 ,2-dimethoxyethane (200 ml) and 2,6-diethyl-4- methylphenylboronic acid (6.5Og, 33.8 mmol), palladium(ll) acetate (0.5 g, 2.23 mmol), and lithium hydroxide monohydrate (5.05g, 120.0 mmol) are added at 0C. The mixture is warmed to 50C and as it thickens after ca. 1-2 hours, it is further diluted with a mixture of water and 1 ,2- dimethoxyethane (50 + 50 ml). After addition of a further catalytic amount of palladium(ll) acetate, stirring at 50C is continued for about 16 hours.The reaction mixture is diluted with ethyl acetate and water, and the alkaline water layer is extracted twice with ethyl acetate. The combined organic layer is discarded and the aqueous phase further diluted with ethyl acetate and acidified at 0C to pH 2-3 using 4N aqueous hydrochloric acid. The organic layer is separated, the water layer is extracted twice with ethyl acetate, the combined organic phases dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo.The crude product is purified by flash filtration first (ethyl acetate / hexane 3:1), followed by flash chromatography (ethyl acetate / hexane 3:2?2:1 ). The yellowish oil obtained after concentration is taken up in a 4 : 1 mixture of hexane : tert-butyl methyl-ether, the mixture stirred, and the white solid is collected by filtration to give 9-(2,6-diethyl-4-methylphenyl)-3-oxaspiro[5.5]undecane- 8,10-dione, m.p. 139-141 C.deltaH (CDCI3) 6.97 (s, 2H), 5.83 (br s, 1 H), 3.72 (t, 4H), 2.59 (br s, 4H), 2.39-2.27 (m, 4H), 2.32 (s, 3H), 1.69 (t, 4H), 1.06 (t, 6H)

Reference： [1]Patent: WO2008/110308,2008,A2 .Location in patent: Page/Page column 42

7
[ 953075-90-6 ]
C₁₆H₁₉IO₂S [ No CAS ]
[ 1067594-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide;palladium diacetate; In 1,2-dimethoxyethane; water; at 50℃; for 4.75h;	Step 5The iodonium ylide (1.90 g, 4.56 mmol), prepared in Step 4, <strong>[953075-90-6]2,6-diethyl-4-methyl-phenylboronic acid</strong> (1.05 g, 5.48 mmol), palladium (II) acetate (0.082 g, 0.36 mmol), lithium hydroxide monohydrate (0.766 g, 18.24 mmol) are stirred together a mixture of 1 ,2-dimethoxyethane (40 ml) and water (10 ml) under an atmosphere of nitrogen and then heated to 5OC for 4.75 hours. The mixture is cooled to room temperature, filtered through celite, and the celite washed with 2M aqueous hydrochloric acid (80 ml) and 40ml ethyl acetate (40 ml). The mixture is poured into a separating funnel, the organic layer is separated, and the aqueous layer is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate is evaporated in vacuo to give a brown gum. Purification by column chromatography on silica gel gives 2-(2,6-diethyl-4-methylphenyl)-5-[2-(ethylthio)propyl]- cyclohexane-1 ,3-dione as a pale yellow gum. deltaH (CDCI3) 6.98 (d, 2H), 5.52 (d, 1 H), 2.93-2.83 (m, 1 H), 2.21-2.76 (m, 11 H), 2.33 (s, 3H), 1.78- 1.59 (m, 2H), 1.34 (dd, 3H), 1.27 (m, 3H), 1.08 (m, 6H)

Reference： [1]Patent: WO2008/110308,2008,A2 .Location in patent: Page/Page column 40

8
[ 953075-90-6 ]
[ 14203-25-9 ]
[ 1112412-88-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In toluene; at 90℃; for 6.5h;	Step 2: Preparation of 2-(2,6-diethyl-4-rnethylphenyl)-3-methoxycyclopent-2-enone.;To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (17.5 g, 91.6 mmol), 2,6- diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol) and freshly powdered potassium phosphate (38.9 g, 183 mmol) in anhydrous, degassed toluene (450 ml) under a nitrogen atmosphere are added palladium (II) acetate (0.411 g, 1.83 mmol) and 2-dicyclohexylphosphino- <n="56"/>2',6'-dimethoxybiphenyl (1.51 g, 3.67 mmol). The reaction mixture is heated at 90C for 6.5 hours and then allowed to cool to room temperature overnight. The reaction is diluted with water (400 ml) and extracted with ethyl acetate (3 x 150 ml). The combined organic extracts are washed with brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In toluene; at 90℃; for 6.5h;Inert atmosphere;	To a stirred suspension of 2-bromo-3-methoxy-cyclopent-2-en-1 -one (17.5 g, 91.6 mmol), 2,6- diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol) and freshly powdered potassium phosphate (38.9 g, 183 mmol) in anhydrous, degassed toluene (450 ml) under a nitrogen atmosphere are added palladium (II) acetate (0.411 g, 1.83 mmol) and 2-dicyclohexylphosphino- 2?,6?-dimethoxybiphenyl (1 .51 g, 3.67 mmol). The reaction mixture is heated at 90C for 6.5 hours and then allowed to cool to room temperature overnight. The reaction is diluted with water (400 ml) and extracted with ethyl acetate (3 x 150 ml). The combined organic extracts are washed with brine (50 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-3-methoxy-cyclopent-2-en- 1- one.

Reference： [1]Patent: WO2009/19005,2009,A2 .Location in patent: Page/Page column 54-55
[2]Patent: WO2014/195327,2014,A1 .Location in patent: Page/Page column 109; 110

9
[ 953075-90-6 ]
(1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.0(2,6)]dec-4-en-3-one [ No CAS ]
(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.0(2,6)]dec-4-en-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In toluene; at 95℃; for 24h;	Step 3: Preparation of (1RS, 2SR, 6RS, 7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10- oxatricyclo[5.2.1.026]dec-4-en-3-one.; <n="60"/>A mixture of (1RS, 2SR, 6RS, 7Sf?)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.026]dec-4-en-3-one (0.315 g, 1.2 mmol), <strong>[953075-90-6]2,6-diethyl-4-methylphenylboronic acid</strong> (0.35 g, 1.8 mmol), 2-dicyclo- hexylphosphino-2',6'-dimethoxybiphenyl (20 mg, 0.048 mmol), palladium (II) acetate (5.5 mg, 0.024 mmol) and potassium phosphate (0.51 g, 2.4 mmol) are heated in degassed toluene at 95 0C for 24 hours. The reaction mixture is partitioned between dichloromethane and water, and the organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give (yRS,2Sf?,6RS, 7Sf?)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.02\|6]dec-4- en-3-one.1H NMR (400MHz, CDCI3) deltaH 6.90 (1 H, s), 6.80 (1 H, s), 4.73 (1 H, d), 4.66 (1 H, d), 3.58 (3H, s), 2.91 (1 H, d), 2.66 (1 H, d), 2.50 - 2.36 (4H, m), 2.30 (3H, s), 1.88 -1.81 (2H, m), 1.62 - 1.56 (2H, m), 1.12 - 1.09 (6H1 m).

Reference： [1]Patent: WO2009/19005,2009,A2 .Location in patent: Page/Page column 58-59

10
[ 953075-90-6 ]
C₁₅H₁₃IO₃ [ No CAS ]
C₂₀H₂₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide; tetrabutylammomium bromide;palladium diacetate; In 1,2-dimethoxyethane; water; at 50℃; for 5h;	The iodonium ylide (3 g, 8.15 mmol), prepared above, is added to a solution of 2,6-diethyl-4- methylphenylboronic acid (1.57 g, 8.15 mmol), tetrabutylammonium bromide (2.63 g, 8.15 mmol), lithium hydroxide monohydrate (1.03 g, 24.5 mmol) and palladium (II) acetate (92 mg, 0.41 mmol) in 1 ,2-dimethoxyethane (80 ml) and water (20 ml) and the reaction mixture is heated at 5O0C for 5 hours under an atmosphere of nitrogen. The reaction mixture is cooled to room temperature and partitioned between dilute aqueous hydrochloric acid and ethyl acetate. The organic phase is then extracted into 0.5 M aqueous potassium carbonate solution and the organic phase discarded. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract is dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to afford (^f?S,2Sf?,6f?S, 7SR)-4-(2,6-diethyl-4-methylphenyl)-10- oxatricyclo[5.2.1.02'6]decane-3,5-dione.1H NMR (400MHz, CDCI3) deltaH 6.88 - 6.87 (2H , m), 4.55 - 4.54 (2H, m), 2.62 (2H, s), 2.36 - 2.27 (7H, m), 1.69 - 1.67 (2H, m), 1.40 - 1.39 (2H, m), 1.03 (6H, q).

Reference： [1]Patent: WO2009/19005,2009,A2 .Location in patent: Page/Page column 53

11
[ 953075-90-6 ]
[ 1221888-43-2 ]
2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4-ylmethyl)cyclohexane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; tetrabutyl ammonium fluoride;palladium diacetate; In 1,2-dimethoxyethane; at 50℃; for 3h;	Step 5b The iodonium ylide (193 mg, 0.47 mmol) prepared in Step 5a is added to a mixture of 2,6-diethyl- 4-methylphenylboronic acid (90 mg, 0.47 mmol), tetrabutylammonium bromide (151 mg, 0.47 mmol), lithium hydroxide monohydrate (60 mg, 1.4 mmol) and palladium (II) acetate (catalytic amount) in aqueous 1 ,2-dimethoxyethane and the reaction mixture is heated at 5O0C for 3 hours. The reaction is then cooled, dilute aqueous hydrochloric acid is added, and the mixture is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4- ylmethyl)cyclohexane-1 ,3-dione1H NMR (CDCI3, ppm) delta 7.0 (s, 2H), 5.50 (br s, 1 H), 3.98 (br dd, 2H), 3.40 (br t, 2H), 2.68 - 2.63 (m, 2H), 2.45 - 2.25 (m, 10H), 1.69 - 1.55 (m, 3H), 1.44 (br t, 2H), 1.35 - 1.20 (m, 2H), 1.08 (q, 6H).

Reference： [1]Patent: WO2010/46194,2010,A1 .Location in patent: Page/Page column 47-48

12
[ 953075-90-6 ]
C₁₆H₁₇IO₄ [ No CAS ]
[ 1221887-79-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; tetrabutyl ammonium fluoride;palladium diacetate; In 1,2-dimethoxyethane; water; at 55℃; for 5h;	Step 3bThe iodonium ylide (477 mg, 1.19 mmol) prepared in Step 3a is added to a mixture of 2,6-diethyl- 4-methylphenylboronic acid (343 mg, 1.79 mmol), tetrabutylammonium bromide (385 mg, 1.19 mmol), lithium hydroxide monohydrate (151 mg, 3.57 mmol) and palladium (II) acetate (13 mgs) in a mixture of 1 ,2-dimethoxyethane (10.8 ml) and water (2.7 ml) and the reaction mixture is heated at 550C for 5 hours. The reaction is then cooled, dilute aqueous hydrochloric acid is added, and the mixture is extracted with ethyl acetate. The organic extracts are combined, washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4- methylphenyl)-5-([1 ,3]dioxolan-2-ylmethyl)cyclohexane-1 ,3-dione1H NMR (CDCI3, ppm) deltaH 6.98 (br s, 2H), 4.98 (t, 1 H), 4.01 - 3.88 (2 X m, 4 H), 2.75 (m, 2H), 2.60 - 2.25 (m, 10 H), 1 .85 (m, 2H), 1.05 (m, 6H)

Reference： [1]Patent: WO2010/46194,2010,A1 .Location in patent: Page/Page column 50

13
[ 953075-90-6 ]
C₁₇H₁₇IO₂ [ No CAS ]
rac-(7R,8S)-2-(2,6-diethyl-4-methylphenyl)hexahydro-4,7-ethanoindene-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide monohydrate; tetrabutylammomium bromide;palladium diacetate; In 1,2-dimethoxyethane; water; at 50 - 52℃; for 4.5h;	Step 2To a suspension of iodonium ylide (1.28 g, 3.37mmol) in a mixture of 1 ,2-dimethoxyethane (32 ml) and water (8 ml) is added <strong>[953075-90-6]2,6-diethyl-4-methylphenylboronic acid</strong> (0.497 g, 3.70mmol), then lithium hydroxide monohydrate (0.424 g, 10.10mmol), tetrabutyl ammonium bromide (0.112 g, 0.34mmol) and palladium(ll) acetate (0.038 g, 0.17mmol). The reaction mixture is heated to 50- 52C for 4.5 hours, then cooled to room temperature. A solution of 2M aqueous hydrochloric acid (50ml) is added. Ethyl acetate is then added, and the biphasic mixture is filtered through diatomaceous earth. The organic phase is collected, and the aqueous phase is extracted again with ethyl acetate. The organic extracts are combined, dried over magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by flash column chromatography (100% hexane to 100% ethyl acetate eluant) to afford rac-(7R,8S)-2-(2,6- diethyl-4-methylphenyl)hexahydro-4,7-ethanoindene-1 ,3-dione (0.101g) as a yellow solid.

Reference： [1]Patent: WO2010/133232,2010,A1 .Location in patent: Page/Page column 76

14
[ 953075-90-6 ]
[ 105-36-2 ]
[ 1176272-82-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8107 - 8112

15
[ 953075-90-6 ]
C₁₇H₁₇IO₂ [ No CAS ]
C₂₂H₂₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 2 To a suspension of iodonium ylide (1.28 g, 3.37 mmol) in a mixture of 1,2-dimethoxyethane (32 ml) and water (8 ml) is added <strong>[953075-90-6]2,6-diethyl-4-methylphenylboronic acid</strong> (0.497 g, 3.70 mmol), then lithium hydroxide monohydrate (0.424 g, 10.10 mmol), tetrabutyl ammonium bromide (0.112 g, 0.34 mmol) and palladium(II) acetate (0.038 g, 0.17 mmol). The reaction mixture is heated to 50-52 C. for 4.5 hours, then cooled to room temperature. A solution of 2M aqueous hydrochloric acid (50 ml) is added. Ethyl acetate is then added, and the biphasic mixture is filtered through diatomaceous earth. The organic phase is collected, and the aqueous phase is extracted again with ethyl acetate. The organic extracts are combined, dried over magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by flash column chromatography (100% hexane to 100% ethyl acetate eluant) to afford rac-(7R,8S)-2-(2,6-diethyl-4-methylphenyl)hexahydro-4,7-ethanoindene-1,3-dione (0.101 g) as a yellow solid.

Reference： [1]Patent: US2012/65066,2012,A1 .Location in patent: Page/Page column 34-35

16
[ 953075-90-6 ]
[ 546-67-8 ]
C₁₁H₁₆*HPb⁽³⁺⁾*3C₂H₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21 g		At RT under nitrogen atmosphere, lead tetraacetate26.5 g, mercury acetate 0.83 g and a compound of formula (19-1) 10 g were dissolved in chloroform 110 ml. Theresulting solution was stirred at RT under nitrogen atmosphere for 15 minutes. The resulting solution was then stirred at 4000 under nitrogen atmosphere for 4 hours. The reaction solution was cooled to RT and then filtered through Celite (registered trademark) and the filtrate wasconcentrated under reduced pressure to afford yellow oil. To the obtained oil was added hexane, and the resulting mixture was concentrated under reduced pressure to afford yellow solid. At RT under nitrogen atmosphere, the obtained solid was dissolved in chloroform 260 ml. To theresulting solution was added potassium carbonate 86.2 g and the resulting mixture was stirred for 10 minutes. The reaction solution was then filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure to afford a compound of formula (4-1) 21 g.

Reference： [1]Patent: WO2014/84407,2014,A1 .Location in patent: Paragraph 0137

17
[ 953075-90-6 ]
[ 546-67-8 ]
C₁₁H₁₅^(1-)*Pb⁽⁴⁺⁾*3C₂H₃O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21 g	With mercury(II) diacetate; In chloroform; at 40℃; for 4h;Inert atmosphere;	Under nitrogen atmosphere, at RT, lead tetraacetate 26.5 g, mercury acetate 0.83 g and the compound of the formula (5-1) 10 g were dissolved in chloroform 110 ml. The resulting solutions were stirred at RT under nitrogen atmosphere for 15 minutes. Thereafter, under nitrogen atmosphere, the reaction solutions were stirred at 40 C. for 4 hours. The reaction solutions were cooled to rt and filtered through Celite. The resulting filtrates were concentrated under reduced pressure to give yellow oils. To the oils was added hexane and the resulting mixtures were concentrated under reduced pressure to yellow solids. Under nitrogen atmosphere, at RT, the resulting solids were dissolved in chloroform 260 ml. To the resulting solutions was added potassium carbonate 86.2 g and the resulting mixtures were stirred quickly for 10 minutes. Thereafter, the reaction solutions were filtered through Celite. The resulting filtrates were concentrated under reduced pressure to give the compound of the formula (3-1) 21 g. [0380] 1H NMR (CDCl3) [0381] delta ppm: 7.05 (2H, s), 2.90 (4H, m), 2.35 (3H, s), 2.06 (9H, s), 1.33-1.27 (6H, m)

Reference： [1]Patent: US2014/228219,2014,A1 .Location in patent: Paragraph 0378-0381

18
[ 953075-90-6 ]
[ 1415576-44-1 ]