[ CAS No. 79023-51-1 ] {[proInfo.proName]}

Name: 79023-51-1|1,3,3-Trimethyl-3,4-dihydroisoquinoline|95%
Brand: Ambeed
SKU: A932233
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Quality Control of [ 79023-51-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79023-51-1 ]

SDS Specification

Alternatived Products of [ 79023-51-1 ]

Product Details of [ 79023-51-1 ]

CAS No. :	79023-51-1	MDL No. :	MFCD00608546
Formula :	C₁₂H₁₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFNOAVXTUXLYNM-UHFFFAOYSA-N
M.W :	173.25	Pubchem ID :	594161
Synonyms :

Calculated chemistry of [ 79023-51-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.54
TPSA :	12.36 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.52
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	2.58
Log Po/w (SILICOS-IT) :	4.04
Consensus Log Po/w :	2.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.66
Solubility :	0.379 mg/ml ; 0.00218 mol/l
Class :	Soluble
Log S (Ali) :	-2.12
Solubility :	1.3 mg/ml ; 0.0075 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.41
Solubility :	0.0068 mg/ml ; 0.0000393 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

Safety of [ 79023-51-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 79023-51-1 ]

* 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 [ 79023-51-1 ]

[ 79023-51-1 ] Synthesis Path-Downstream 1~109

1
[ 79023-51-1 ]
[ 79-37-8 ]
[ 113417-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; at 0℃; for 2.25h;	A) 5,5-Dimethyl-5,6-dihydro-pyrrolo[2,1a]isoquinoline-2,3-dione To a solution of oxalyl chloride (0.86 ml, 10 mmol) in anhydrous ether (50 ml) is added a solution of 1,1,3-trimethyl-3,4-dihydroisoquinoline (2.09 g, 10 mmol) in triethylamine (2.76 ml, 20 mmol) and ether (100 ml) within 15 minutes under nitrogen at 0C. The mixture is stirred for additional 2 h.. The reaction mixture is diluted with water, extracted with ether, washed with brine, dried over Na2SO4 and concentrated.. Purification of the crude product by chromatography (20% ethyl acetate/hexanes) affords the title compound, mp 122-124C.

Reference： [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 790 - 792
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 963 - 965
[2]Patent: EP1433789,2004,A1 .Location in patent: Page 14

2
[ 79023-51-1 ]
[ 58303-62-1 ]
[ 82381-01-9 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 320 - 320

3
[ 79023-51-1 ]
[ 67-66-3 ]
[ 132092-61-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 909 - 913
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 1086 - 1091
[2]Synthesis,1997,p. 677 - 680

4
[ 79023-51-1 ]
[ 13089-11-7 ]
[ 129762-48-7 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1268 - 1272
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1405 - 1410

5
[ 79023-51-1 ]
[ 1113-69-5 ]
4-amino-6,6-dimethyl-2,2-bis(trifluoromethyl)-3-cyano-6,7-dihydro-2H-benzo<a>quinolizine [ No CAS ]

Reference： [1]Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.),1992,vol. 41,p. 1474 - 1476
Izvestiya Akademi Nauk, Seriya Khimicheskaya,1992,p. 1888 - 1892

6
[ 79023-51-1 ]
[ 13081-18-0 ]
[ 129762-51-2 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1268 - 1272
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1405 - 1410

7
[ 79023-51-1 ]
[ 69746-38-9 ]
[ 79023-52-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 320 - 320

8
[ 79023-51-1 ]
[ 41565-97-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 871 - 874
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 1089 - 1091

9
[ 100-86-7 ]
[ 105-56-6 ]
[ 79023-51-1 ]

Yield	Reaction Conditions	Operation in experiment
		B) 1,1,3-Trimethyl-3,4-dihydroisoquinoline To a solution of ethyl cyanoacetate (4.14 g, 33.3 mmol) in dry benzene (85 ml) is added concentrated sulfuric acid keeping the temperature below 5C. After 30 minutes a solution of 2-methyl-1 -phenyl-propan-2-ol in benzene (55 ml) is added over a period of 30 minutes.. The reaction mixture is refluxed for 2.5 h and poured onto ice.. The organic layer is separated and neutralized with concentrated ammonia, extracted with ether, dried and concentrated.. Purification by chromatography (40% ethyl acetate/hexanes) gives the title compound as light yellow oil.

Reference： [1]Chemistry of Heterocyclic Compounds,1983,vol. 19,p. 1242
Khimiya Geterotsiklicheskikh Soedinenii,1983,p. 1560
[2]Patent: EP1433789,2004,A1 .Location in patent: Page 14

10
[ 79023-51-1 ]
[ 684-16-2 ]
[ 129788-82-5 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1268 - 1272
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1405 - 1410
[2]Journal of Fluorine Chemistry,1991,vol. 54,p. 275
[3]Journal of Fluorine Chemistry,1991,vol. 54,p. 275

11
[ 100-86-7 ]
[ 75-05-8 ]
[ 79023-51-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid; at 5 - 20℃; for 5.08333h;	100.6 ml of concentrated sulfuric acid (9.4 eq.) are placed in a 500 ml three-necked flask equipped with a condenser and a thermometer, followed by cooling to a temperature in the region of 5- 10C. A mixture containing 30 g of methyl- 1 -phenyl-2-propanol (1 eq.) and 9.83 g of acetonitrile (1 eq.) is added dropwise. The mixture is stirred for 5 minutes at a temperature in the region of 5-10C and then for 5 hours at room temperature (monitoring by TLC, 95/5 CH2Cl2/MeOH). (0210) The mixture is then poured into 1 litre of water and extracted with 100 ml of toluene. The aqueous phase is basified to pH 8.5 with ammonium carbonate and then extracted twice with 500 ml of MTBE (methyl tert-butyl ether). The organic phase is dried over Na2S04, filtered, evaporated to dryness and then dried under vacuum over P205. 27 g (78% yield) of compound (a) are obtained in the form of a yellow liquid. (0211) The NMR and mass analyses are in accordance with the expected structure.
74%	With sulfuric acid; at 0 - 20℃; for 1h;	Example 2: This example illustrates the preparation of 3,3-dimethyl-1 -pyrrolo[1 ,2-b]pyridazin- 3-yl-4H-isoquinolinea) Preparation of 1 ,3,3-trimethyl-4H-isoquinolineAcetonitrile (1.5 g, 37 mmol) was slowly added to 98% sulfuric acid (50 g, 0.5 mol) at 0 00. Then 2-methyl-i -phenyl-propan-2-ol (5.0 g, 33 mmol) was added to this solution at 0 00 The reaction mixture was allowed to reach room temperature, stirred for 1 h at this temperature and poured on aqueous sodium hydroxide solution of pH 9. The mixture was extracted withethyl acetate, the organic layer washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure to obtain 1 ,3,3-trimethyl-4H-isoquinoline (4.3 g, 25 mmol, 74 %), which was pure enough to be directly used in the next step. 1H-NMR (400 MHz, 0D013): oe (ppm) = 1.20 (s, 6H), 2.37 (s, 3H), 2.69 (s, 2H), 7.14 (d, 1H), 7.27-7.36 (m, 2H), 7.48 (d, 1H).
	With sulfuric acid; In benzene; at 20℃; for 24h;	REFERENCE EXAMPLE 2 1,3,3-trimethyl-3,4-dihydroisoquinolin To conc. sulfuric acid (10 ml) was added a solution of 2-methyl-1-phenylpropan-2-ol (7.0 g) and acetonitrile (1.62 ml) in benzene (7.0 ml) dropwise and the mixture was stirred for 24 hours at room temperature.The mixture was neutralized by adding to a mixture of ice and a saturated aqueous solution of sodium bicarbonate dropwise, and it was extracted with ethyl acetate twice.The extract was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure.The residue was dissolved in ether and was extracted with 1 N hydrochloric acid and 2N hydrochloric acid.The extract was washed with ether and to the mixture was added 5N aqueous solution of sodium hydroxide and was extracted with ether twice.The extract was washed with water and a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to give the title compound (2.53 g) having the following physical data. TLC: Rf 0.22 (hexane:ethyl acetate=2:1); NMR (CDCl3): delta 7.48 (dd, J=7.5, 1.5 Hz, 1H), 7.35 (dt, J=1.5, 7.5 Hz, 1H), 7.30-7.25 (m, 1H), 7.14 (d, J=7.5 Hz, 1H), 2.69 (s, 2H), 2.38 (s, 3H), 1.20 (s, 6H).

Reference： [1]Synthetic Communications,2012,vol. 42,p. 2181 - 2190
[2]Journal of Chemistry,2015,vol. 2015
[3]Patent: WO2017/109185,2017,A1 .Location in patent: Page/Page column 25; 26
[4]Patent: WO2015/117563,2015,A1 .Location in patent: Page/Page column 77
[5]Patent: WO2018/208132,2018,A1 .Location in patent: Paragraph 368-372
[6]Pharmaceutical Chemistry Journal,1989,vol. 23,p. 133 - 136
Khimiko-Farmatsevticheskii Zhurnal,1989,vol. 23,p. 172 - 176
[7]Patent: US2004/77643,2004,A1 .Location in patent: Page 52, 53

12
[ 79023-51-1 ]
[ 55991-67-8 ]
[ 79023-53-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 320 - 320

13
[ 79023-51-1 ]
[ 74-88-4 ]
[ 120402-42-8 ]

Reference： [1]Pharmaceutical Chemistry Journal,1989,vol. 23,p. 133 - 136
Khimiko-Farmatsevticheskii Zhurnal,1989,vol. 23,p. 172 - 176

14
[ 79023-51-1 ]
[ 55991-68-9 ]
[ 82392-82-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 320 - 320

15
[ 79023-51-1 ]
[ 55991-70-3 ]
[ 82381-02-0 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1982,vol. 18,p. 320 - 320

16
[ 79023-51-1 ]
[ 2048-57-9 ]
2-(3,3-Dimethyl-3,4-dihydro-2H-isoquinolin-1-ylidene)-N,N'-di-thiophen-2-yl-malonamide [ No CAS ]