[ CAS No. 932-01-4 ] {[proInfo.proName]}

Name: 932-01-4|4,4-Dimethylcyclohexanol|97%
Brand: Ambeed
SKU: A519007
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2D 3D

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Quality Control of [ 932-01-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 932-01-4 ]

SDS Specification

Alternatived Products of [ 932-01-4 ]

Product Details of [ 932-01-4 ]

CAS No. :	932-01-4	MDL No. :	MFCD00101954
Formula :	C₈H₁₆O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VUQOIZPFYIVUKD-UHFFFAOYSA-N
M.W :	128.21	Pubchem ID :	136735
Synonyms :

Calculated chemistry of [ 932-01-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.36
TPSA :	20.23 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) :	-5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	1.96
Consensus Log Po/w :	1.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.89
Solubility :	1.63 mg/ml ; 0.0127 mol/l
Class :	Very soluble
Log S (Ali) :	-2.05
Solubility :	1.14 mg/ml ; 0.00888 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.47
Solubility :	4.39 mg/ml ; 0.0343 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 932-01-4 ]

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 [ 932-01-4 ]

* 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 [ 932-01-4 ]
Downstream synthetic route of [ 932-01-4 ]

[ 932-01-4 ] Synthesis Path-Upstream 1~9

1
[ 1073-13-8 ]
[ 932-01-4 ]

Reference： [1] European Journal of Organic Chemistry, 2000, # 9, p. 1793 - 1797
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 5986,5990
[3] Helvetica Chimica Acta, 1977, vol. 60, # 2, p. 482 - 494

2
[ 4255-62-3 ]
[ 932-01-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2365 - 2369
[2] Bulletin des Societes Chimiques Belges, 1980, vol. 89, # 5, p. 389 - 398
[3] Journal of the American Chemical Society, 1968, vol. 90, # 23, p. 6486 - 6492
[4] Journal of the American Chemical Society, [5] Journal of the American Chemical Society, 2009, vol. 131, p. 251 - 262
[6] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7321 - 7326

3
[ 634905-74-1 ]
[ 932-01-4 ]

Reference： [1] Synthetic Communications, 2003, vol. 33, # 11, p. 1951 - 1961

4
[ 78-94-4 ]
[ 78-84-2 ]
[ 932-01-4 ]

Reference： [1] Journal of the American Chemical Society, 1968, vol. 90, # 23, p. 6486 - 6492

5
[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]

Reference： [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 484 - 486

6
[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]
[ 4255-62-3 ]

Reference： [1] Tetrahedron, 1980, vol. 36, p. 1937 - 1942
[2] European Journal of Organic Chemistry, 2000, # 9, p. 1793 - 1797

7
[ 24463-33-0 ]
[ 932-01-4 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1913, vol. 401, p. 313[2] Justus Liebigs Annalen der Chemie, 1915, vol. 409, p. 164

8
[ 6611-78-5 ]
[ 932-01-4 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1913, vol. 401, p. 313[2] Justus Liebigs Annalen der Chemie, 1915, vol. 409, p. 164

9
[ 590-66-9 ]
[ 2979-19-3 ]
[ 1193-46-0 ]
[ 932-01-4 ]
[ 767-12-4 ]
[ 1193-47-1 ]
[ 4255-62-3 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 50, p. 15833 - 15842

[ 932-01-4 ] Synthesis Path-Downstream 1~58

1
[ 85-44-9 ]
[ 932-01-4 ]
[ 109652-63-3 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 5986,5990
[2]Journal of the American Chemical Society,1968,vol. 90,p. 6486 - 6492

2
[ 1073-13-8 ]
[ 932-01-4 ]

Reference： [1]European Journal of Organic Chemistry,2000,p. 1793 - 1797
[2]Journal of the American Chemical Society,1957,vol. 79,p. 5986,5990
[3]Helvetica Chimica Acta,1977,vol. 60,p. 482 - 494

3
[ 932-01-4 ]
[ 14072-86-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 167
[2]Canadian Journal of Chemistry,1964,vol. 42,p. 212 - 222
[3]Journal of the Chemical Society. Perkin transactions II,1979,p. 1535 - 1539

4
[ 932-01-4 ]
[ 4255-62-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 401,p. 313
Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 164

5
[ 24463-33-0 ]
[ 932-01-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 401,p. 313
Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 164

6
[ 932-01-4 ]
[ 98-59-9 ]
[ 26059-37-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1973,p. 128 - 132

7
[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]
[ 4255-62-3 ]

Reference： [1]Tetrahedron,1980,vol. 36,p. 1937 - 1942
[2]European Journal of Organic Chemistry,2000,p. 1793 - 1797

8
[ 4255-62-3 ]
[ 932-01-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2365 - 2369
[2]Bulletin des Societes Chimiques Belges,1980,vol. 89,p. 389 - 398
[3]Journal of the American Chemical Society,1968,vol. 90,p. 6486 - 6492
[4]Journal of the American Chemical Society,2009,vol. 131,p. 251 - 262
[5]Organic and Biomolecular Chemistry,2012,vol. 10,p. 7321 - 7326

9
[ 932-01-4 ]
[ 115-11-7 ]
t-butoxy-4,4-dimethylcyclohexane [ No CAS ]

Reference： [1]Organic Mass Spectrometry,1989,vol. 24,p. 615 - 619

10
[ 78-94-4 ]
[ 78-84-2 ]
[ 932-01-4 ]

Reference： [1]Journal of the American Chemical Society,1968,vol. 90,p. 6486 - 6492

11
[ 1073-13-8 ]
[ 932-01-4 ]
[ 5020-09-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 484 - 486

15
1-methyl-dichloromethyl-cyclohexadien-(2.5)-one-⁽⁴⁾ [ No CAS ]
[ 932-01-4 ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 787,789

16
[ 56-23-5 ]
[ 64-17-5 ]
[ 6611-78-5 ]
Raney nickel [ No CAS ]
[ 932-01-4 ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 787,789

17
[ 60-29-7 ]
[ 24463-33-0 ]
sodium [ No CAS ]
[ 932-01-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 401,p. 313
Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 164

18
[ 634905-74-1 ]
[ 932-01-4 ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1951 - 1961

19
[ 932-01-4 ]
[ 106-95-6 ]
4-allyloxy-1,1-dimethylcyclohexane [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7973 - 7981

20
[ 932-01-4 ]
1,1-Dimethyl-4-[((E)-propenyl)oxy]-cyclohexane [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7973 - 7981

21
[ 932-01-4 ]
1,1-dimethyl-4-propoxy-cyclohexane [ No CAS ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 7973 - 7981

22
[ 6611-78-5 ]
[ 932-01-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1913,vol. 401,p. 313
Justus Liebigs Annalen der Chemie,1915,vol. 409,p. 164

23
[ 932-01-4 ]
[ 25186-25-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1973,p. 128 - 132

24
[ 193971-80-1 ]
[ 932-01-4 ]
C₁₆H₁₇F₅N₄O₂S [ No CAS ]

Reference： [1]Patent: US6362134,2002,B1 .Location in patent: Page column 279

25
[ 110-05-4 ]
[ 932-01-4 ]
[ 140-88-5 ]
[ 96517-19-0 ]

Yield	Reaction Conditions	Operation in experiment
96.3%		In a 500ml three necked round bottom flask was charged <strong>[932-01-4]4,4-dimethyl-cyclohexanol</strong> (100g, 0.78mol) and heated up to 160C, while adding over 4 hours tBuOOtBu (11.4g, 0.08mol) and ethylacrylate (39.2g, 0.39mol). 10 minutes after the end of the addition, the mixture was cooled to 50C and lights were distilled off. Then, 30% w/w aqueous NaOH (61g) and MTBE (200g) were added. Stirring was continued during the night at 40C and the aqueous phase was separated. The aqueous phase was re-extracted four times with MTBE (200g). Afterwards, MTBE (200g) was added to the aqueous phase, and the pH adjusted to 1 with 50% w/w aqueous H2SO4. The organic phase was washed with water and concentrated to yield 49.4g of crude 8,8-dimethyl-1-oxa-spiro[4.5]decan-2-one (GC purity: 96.3%).

Reference： [1]Patent: EP1529770,2005,A1 .Location in patent: Page/Page column 5

26
[ 932-01-4 ]
[ 1073-13-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 251 - 262

27
[ 932-01-4 ]
[ 1225346-74-6 ]
[ 1225348-65-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;	To a mixture of 4,4-Dimethylcyclohexanol (63.2 mg, 0.000493 mol), (R)-4-(6- hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (100 mg, 0.0004 mol), 5 triphenylphosphine (129 mg, 0.000493 mol), and tetrahydrofuran (4 mL, 0.05 mol), diisopropyl azodicarboxylate (0.0971 mL, 0.000493 mol ) was added dropwise and was stirred at room temperature overnight. The mixture was diluted with EA and washed with 5% citric acid and brine then dried with magnesium sulfate and concentrated. The crude was taken up into DCM and subjected to ISCO combiflash purification with EtOAc/hexane (0- I0 70) to give product.

Reference： [1]Patent: WO2010/51030,2010,A1 .Location in patent: Page/Page column 44

28
[ 932-01-4 ]
[ 1233865-62-7 ]
C₃₆H₄₁NO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃;	4,4-DimethyIcyclohexanol (65 mg, 0.510 mmol), triphenylphosphine (134 mg, 0.510 mmol) and DEAD (89 mg, 0.510 mmol) was added to a mixture of 1-(4-hydroxyphenyl)-5- (4-isopropoxyphenoxy)-2-methoxycarbonylmethylindole-3-carboxylic acid methyl ester (125 mg, 0.255 mmol, (see Example 1 :2, step (a)) and THF (4 ml_). The mixture was stirred at rt overnight. Extractive workup (EtOAc, water), drying (Na2SO4), concentration and purification by chromatography, followed by hydrolysis in accordance with Example 1 :1 , step (c) gave the title compound. Yield: 57 mg (39%).1H NMR (DMSO-cfe) delta: 12.38 (br s, 2H) 7.61 (d, J = 2.4 Hz, 1H) 7.34-7.27 (m, 2H) 7.19-7.11 (m, 2H) 6.99-6.86 (m, 6H) 4.52 (septet, J = 6 Hz, 1H) 4.47-4.38 (m, 1H) 3.94 (S1 2H), 1.93-1.82 (m, 2H) 1.69-1.57 (m, 2H) 1.52-1.42 (m, 2H) 1.37-1.28 (m, 2H) 1.25 (d, J = 6 Hz, 6H) 0.96 (s, 3H) 0.94 (s, 3H)

Reference： [1]Patent: WO2010/76566,2010,A2 .Location in patent: Page/Page column 42

29
[ 932-01-4 ]
[ 98349-22-5 ]
[ 1224048-13-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2365 - 2369

30
[ 932-01-4 ]
(S)-N-(4-benzyloxy-3-methoxybenzyl)-3-piperidinecarboxamide [ No CAS ]
[ 530-62-1 ]
4,4-dimethylcyclohexyl (S)-3-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		N,N'-carbonyldiimidazole (118 mg) was added to a mixture of <strong>[932-01-4]4,4-dimethylcyclohexanol</strong> (72 mg) and acetonitrile (7 ml). The reaction mixture was stirred at 45C for 1 hour, added with water and chloroform and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The product (190 mg) of the above (2), triethylamine (0.21 ml), 4-dimethylaminopyridine (10 mg) and DMF (5 ml) were added to the residue and the reaction mixture was heated at 80C for 1 hour. The reaction mixture was evaporated under reduced pressure, and water and chloroform were added thereto. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate = 100/0 to 0/100 gradient) to obtain 135 mg of 4,4-dimethylcyclohexyl (S)-3-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.

Reference： [1]Patent: EP2277861,2011,A1 .Location in patent: Page/Page column 22

31
[ 932-01-4 ]
[ 1194062-14-0 ]
[ 530-62-1 ]
[ 1193988-68-9 ]

Yield	Reaction Conditions	Operation in experiment
		(3) N,N'-carbonyldiimidazole (118 mg) was added to a mixture of <strong>[932-01-4]4,4-dimethylcyclohexanol</strong> (72 mg) and acetonitrile (7 ml). The reaction mixture was stirred at 45 C. for 1 hour, added with water and chloroform and washed with water. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The product (190 mg) of the above (2), triethylamine (0.21 ml), 4-dimethylaminopyridine (10 mg) and DMF (5 ml) were added to the residue and the reaction mixture was heated at 80 C. for 1 hour. The reaction mixture was evaporated under reduced pressure, and water and chloroform were added thereto. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 135 mg of 4,4-dimethylcyclohexyl (S)-3-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.

Reference： [1]Patent: US2012/28937,2012,A1 .Location in patent: Page/Page column 18-19

32
[ 932-01-4 ]
[ 1365170-18-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2070 - 2074

33
[ 932-01-4 ]
[ 1365170-37-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2070 - 2074

34
[ 932-01-4 ]
[ 1365170-55-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2070 - 2074

35
[ 932-01-4 ]
[ 1365170-77-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2070 - 2074

36
[ 932-01-4 ]
[ 55084-74-7 ]
[ 1365170-00-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2070 - 2074

37
[ 932-01-4 ]
[ 1436505-22-4 ]

Reference： [1]Patent: WO2013/72825,2013,A1

38
[ 932-01-4 ]
[ 124-63-0 ]
[ 1449214-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 26℃; for 2h;	Method A: To a solution of <strong>[932-01-4]4,4-dimethylcyclohexanol</strong> (100 mg, 0.78 mmol) and Et3N (201 mg, 1.56 mmol) in CH2C12 (2 mL) was added methanesulfonyl chloride (178 mg, 1.56 mmol) at 0C and the reaction mixture was stirred at rt for 2 h before it was quenched with water and was extracted with CH2C12. The organic layer was washed with brine, separated, dried, filtered and concentrated to afford 4,4-dimethylcyclohexyl methanesulfonate which was used without further purification. To a solution of 7-nitrophthalazin-l(2H)-one (Intermediate- 10, step-1 , 100 mg, 0.52 mmol) in THF (2 mL) was added NaH (41 mg, 1.02 mmol, 60% in mineral oil) at 0C and stirred for 15 minutes. Then a solution of 4,4-dimethylcyclohexyl methanesulfonate in THF (1 mL) was slowly added to the reaction mixture at 0C. Then the reaction mixture was heated at 80C for 6 h before it was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 180 mg of the title product/H NMR (300 MHz, DMSO d6): delta 9.27 (s, 1H), 8.59-8.56 (d, / = 8.7 Hz, 1H), 8.30 (s, 1H), 7.88-7.85 (d, / = 8.7 Hz, 1H), 4.97-4.93 (m, 1H), 2.08-1.99 (m, 2H), 1.72-1.67 (m, 2H), 1.57-1.43 (m, 4H), 1.04 (s, 3H), 0.99 (s, 3H).
	With triethylamine; In dichloromethane; at 0 - 20℃; for 13h;	10399] Step 1: To a DCM (45 mE) solution of the 4,4- dimethylcyclohexanol (200 mg, 1.56 mmol) was added tnethylamine(4.9 mE, 35 mmol). The solution was cooled to 0 C. before methanesulfonyl chloride (0.324 mE, 2.34 mmol) was added dropwise. The resulting mixture was allowed to warm to RT over 13 h. The reaction was diluted with DCM and washed with water, the organic phase dried (Na2504), filtered and the filtrate concentrated in vacuo. No further purification was necessary to afford 4,4-dimethylcyclohexyl methanesulfonate.

Reference： [1]Patent: WO2013/72825,2013,A1 .Location in patent: Page/Page column 61; 62
[2]Patent: US2016/151375,2016,A1 .Location in patent: Paragraph 0399

39
[ 89898-94-2 ]
[ 932-01-4 ]
[ 1436505-22-4 ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 4h;Reflux;	Method B: To a solution of 7-nitrophthalazin-l(2H)-one (Intermediate- 10, step-1 , 355 mg, 1.858 mmol) and <strong>[932-01-4]4,4-dimethylcyclohexanol</strong> (356 mg, 2.78 mmol) in THF (6 mL) were added PPh3 (1.22 g, 4.64 mmol) and diisopropyl azodicarboxylate (1.12 g, 5.57 mmol) and the reaction mixture was heated at reflux for 4 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 300 mg of the title product.

Reference： [1]Patent: WO2013/72825,2013,A1 .Location in patent: Page/Page column 62

40
[ 19815-18-0 ]
[ 932-01-4 ]
[ 1449736-75-7 ]

Yield	Reaction Conditions	Operation in experiment
80 mg		To a solution of <strong>[932-01-4]4,4-dimethylcyclohexanol</strong> (140 mg, 1.097 mmol) in THF (2 mL) was added NaH (43 mg, 1.097 mmol, 60% in mineral oil) at 0 C. Then the reaction mixture was stirred at that temperature for 20 min and 4-chloro-8-nitroquinazoline (Intermediate-7, step 2, 115 mg, 0.549 mmol) was added to the reaction mixture. Then the reaction mixture was stirred at 0-5 C. for 4 h and then at rt for 12 h. Then the reaction mixture was quenched with water and was extracted with chloroform. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography using chloroform to afford 80 mg of the title product. 1H NMR (300 MHz, DMSO d6): delta 8.89 (s, 1H), 8.49-8.46 (d, J=7.8 Hz, 1H), 8.45-8.42 (d, J=7.8 Hz, 1H), 7.86-7.80 (t, J=8.4 Hz, 1H), 5.41 (m, 1H), 1.94 (m, 2H), 1.82-1.79 (m, 2H), 1.54 (m, 2H), 1.37-1.34 (m, 2H), 0.99 (s, 3H), 0.67 (s, 3H); MS (m/z): 301.93 (M+H)+.

Reference： [1]Patent: US2013/210844,2013,A1 .Location in patent: Paragraph 0324; 0325

41
[ 932-01-4 ]
7-nitroisoquinoline-1(2H)-one [ No CAS ]
2-(4,4-dimethylcyclohexyl)-7-nitroisoquinolin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100 mg	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 6h;Reflux;	To a solution of 7-nitroisoquinolin-l(2H)-one (100 mg, 0.52 mmol) and 4,4- dimethylcyclohexanol (100 mg, 0.79 mmol) in THF (2 mL) were added PPh3 (342 mg, 1.30 mmol) and diisopropylazodicarboxylate (263 mg, 1.30 mmol) and the reaction mixture was heated at reflux for 6 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 100 mg of the title product. MS (m/z): 301 (M+H)+.

Reference： [1]Patent: WO2014/167444,2014,A1 .Location in patent: Page/Page column 47; 48

42
[ 590-66-9 ]
[ 2979-19-3 ]
[ 1193-46-0 ]
[ 932-01-4 ]
[ 767-12-4 ]
[ 1193-47-1 ]
[ 4255-62-3 ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 15833 - 15842

43
[ 932-01-4 ]
(5-bromo-2-fluorophenyl)(4,4-dimethylcyclohexyl)sulfane [ No CAS ]

Reference： [1]Patent: US2016/151375,2016,A1

44
[ 932-01-4 ]
N-(3-chloro-4-fluorophenyl)-3-((4,4-dimethylcyclohexyl)thio)-4-fluorobenzamide [ No CAS ]

Reference： [1]Patent: US2016/151375,2016,A1

45
[ 932-01-4 ]
[ 394-41-2 ]
4-(4,4-dimethylcyclohexoxy)-2-fluoro-1-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 16h;	Diisopropyl azodiformate (1.3 g, 6.1 mmol) was added dropwise to a solution of triphenylphosphine (1.6 g, 6.1 mmol), 3-fluoro-4-nitrophenol (1.0 g, 6.1 mmol) and 4.4- dimethylcyclohexanol (0.65 g, 5.1 mmol) in 20 ml of tetrahydrofuran. The reaction mixture was stirred for 16 h at room temperature, then diluted with ethyl acetate and water. The phases were separated, the organic layer was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The remainder was purified by chromatography on silica gel, using ethyl acetate and cyclohexane as eluents, to deliver 4-(4,4-dimethylcyclohexoxy)-2-fluoro-1-nitro-benzene. H-NMR (400 MHz, CDCI3): delta = 0.98 (s, 3H), 0.99 (s, 3H), 1.25 - 1.31 (m, 2H), 1 .50 - 1.56 (m, 2H), 1 .69 - 1.77 (m, 2H), 1.86 - 1.92 (m, 2H), 4.32 (q, 1 H), 6.68 - 6.75 (m, 2H), 8.07 (t, 1 H).

Reference： [1]Patent: WO2017/76982,2017,A1 .Location in patent: Page/Page column 50; 51

46
[ 932-01-4 ]
4-(4,4-dimethylcyclohexoxy)-2-fluoroaniline [ No CAS ]

Reference： [1]Patent: WO2017/76982,2017,A1

47
[ 932-01-4 ]
N-[4-(4,4-dimethylcyclohexoxy)-2-fluorophenyl]-1,3-benzoxazole-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/76982,2017,A1

48
[ 932-01-4 ]
[ 151266-23-8 ]
1-(4,4-dimethylcyclohexyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.9 g	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;	6.08 mL of diisopropyl azodicarboxylate was added to a solution of 4 g of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 5.89 g of <strong>[932-01-4]4,4-dimethylcyclohexanol</strong>, and 8.0 g of triphenylphosphine in 30 mL of THF at room temperature, followed by stirring overnight. After concentration, the residue was purified by silica gel chromatography (hexane?hexane/ethyl acetate=1/1), thereby obtaining 3.9 g of the title compound as a white sold. Physical Properties: m/z[M+H]+ 373.1.

Reference： [1]Patent: US2018/9817,2018,A1 .Location in patent: Paragraph 1509; 1510

49
[ 932-01-4 ]
4-amino-1-(4,4-dimethylcyclohexyl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: US2018/9817,2018,A1

50
[ 932-01-4 ]
4-amino-1-(4,4-dimethylcyclohexyl)-N-(5-methyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2018/9817,2018,A1

51
[ 932-01-4 ]
methyl 2-(4-hydroxyphenyl)-4,6-dimethylpyrimidine-5-carboxylate [ No CAS ]
methyl 2-(4-((4,4-dimethylcyclohexyl)oxy)phenyl)-4,6-dimethylpyrimidine-5-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/149419,2018,A1 .Location in patent: Paragraph 00844; 00845

52
[ 32315-10-9 ]
[ 932-01-4 ]
4,4-dimethylcyclohexyl chloroformate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 0.5h;	General procedure: To a solution of phenol (112 mg, 1.2 mmol), triphosgene (178 mg, 0.6 mmol) in CH2Cl2 (10 mL) was added dropwise triethylamine (121 mg, 1.2 mmol) at 0C. The reaction mixture was stirred for 0.5 h and then 3-amino-5-benzylphenol 8 (119 mg, 0.6 mmol) was added. The mixture was stirred at room temperature for 5 h. After the reaction was quenched with water (30 mL), the mixture was extracted with EtOAc (10 mL×3). The combined organic layer was dried over anhydrous Na2SO4, ltered and concentrated in vacuo. The residue was puried by column chromatography (petroleum ether/EtOAc = 4:1) to afford 3a as a white solid (61 mg, 32% yield).