[ CAS No. 1489-69-6 ] {[proInfo.proName]}

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Quality Control of [ 1489-69-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1489-69-6 ]

SDS Specification

Alternatived Products of [ 1489-69-6 ]

Product Details of [ 1489-69-6 ]

CAS No. :	1489-69-6	MDL No. :	MFCD00012261
Formula :	C₄H₆O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	JMYVMOUINOAAPA-UHFFFAOYSA-N
M.W :	70.09	Pubchem ID :	123114
Synonyms :

Calculated chemistry of [ 1489-69-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	19.43
TPSA :	17.07 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.15
Log Po/w (XLOGP3) :	0.18
Log Po/w (WLOGP) :	0.53
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	1.26
Consensus Log Po/w :	0.67

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.32
Solubility :	33.4 mg/ml ; 0.476 mol/l
Class :	Very soluble
Log S (Ali) :	-0.1
Solubility :	56.1 mg/ml ; 0.801 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.28
Solubility :	36.5 mg/ml ; 0.521 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1489-69-6 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P210-P280-P305+P351+P338-P310	UN#:	2924
Hazard Statements:	H225-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1489-69-6 ]

* 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 [ 1489-69-6 ]
Downstream synthetic route of [ 1489-69-6 ]

[ 1489-69-6 ] Synthesis Path-Upstream 1~1

1
[ 131543-46-9 ]
[ 1489-69-6 ]
[ 89532-38-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ammonium hydroxide In methanol at 0 - 20℃;	Compound 44.1. 2-Cyclopropyl-lH-imidazole. Into a 25-mL round-bottom flask, was placed a solution of cyclopropanecarbaldehyde (500 mg, 7.13 mmol), oxaldehyde (455 mg, 7.84 mmol) in methanol (5 mL). The solution was cooled to 0 °C, then 25percent ammonium hydroxide (1 mL) was added drop-wise. The resulting solution was stirred for 3 h at 0 °C, then stirred at room temperature overnight. The resulting mixture was concentrated under reduced pressure and the residue was dissolved in brine (50 mL). The aqueous phase was extracted with ethyl acetate (3 x 10 mL) and the combined organic layers were dried (Na₂S0₄), filtered, and concentrated under reduced pressure to yield 600 mg (78percent) of the title compound as a light brown solid.
78%	With ammonium hydroxide In methanol; water at 0 - 20℃;	Compound 44.1. 2-Cyclopropyl-lH-imidazole. Into a 25-mL round-bottom flask, was placed a solution of cyclopropanecarbaldehyde (500 mg, 7.13 mmol), oxaldehyde (455 mg, 7.84 mmol) in methanol (5 mL). The solution was cooled to 0 °C, then 25percent ammonium hydroxide (1 mL) was added drop-wise. The resulting solution was stirred for 3 h at 0 °C, then stirred at room temperature overnight. The resulting mixture was concentrated under reduced pressure and the residue was dissolved in brine (50 mL). The aqueous phase was extracted with ethyl acetate (3 x 10 mL) and the combined organic layers were dried (Na₂S0₄), filtered, and concentrated under reduced pressure to yield 600 mg (78percent) of the title compound as a light brown solid.

Reference： [1] Patent: WO2014/8197, 2014, A1, . Location in patent: Page/Page column 115
[2] Patent: WO2015/95767, 2015, A1, . Location in patent: Page/Page column 130
[3] Patent: US2011/52578, 2011, A1,
[4] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 605 - 615

[ 1489-69-6 ] Synthesis Path-Downstream 1~10

1
[ 67-56-1 ]
[ 1489-69-6 ]
[ 29882-07-3 ]

Reference： [1]Tetrahedron Letters,1967,p. 4521 - 4524

2
[ 866-23-9 ]
[ 1489-69-6 ]
[ 3167-63-3 ]
[ 58822-70-1 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1980,vol. 99,p. 202 - 206

3
[ 57497-39-9 ]
[ 1489-69-6 ]
(Z)-N-(cyclopropylmethylene)-2-methylpropan-2-amine N-oxide [ No CAS ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 435 - 438

4
[ 535936-86-8 ]
[ 1489-69-6 ]
[ 118317-27-4 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 1523 - 1534

5
[ 13417-49-7 ]
[ 1066-54-2 ]
[ 1489-69-6 ]
1-cyclopropyl-4-(5,6-dihydro-2<i>H</i>-pyran-3-yl)-but-2-yne-1,4-diol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 8273 - 8275

6
[ 615-06-5 ]
[ 1489-69-6 ]
[ 1272565-56-6 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 3300 - 3303

7
[ 773837-37-9 ]
[ 38622-91-2 ]
[ 1489-69-6 ]
[ 89830-98-8 ]

Yield	Reaction Conditions	Operation in experiment
65%		NaCN (360 mg; 7.35 mmol) was added to a suspension of cyclopropane- carboxaldehyde (5 g; 71 .3 mmol) and tosylmethyl-isocyanide (13.7 g; 69.9 mmol) in EtOH (200 mL). The resulting mixture was stirred for 1 h at RT. The solvent was removed under reduced pressure and the residue was washed with a mixture of heptane/ether (1 :1 ). The beige dried powder was stirred in NH3/MeOH 7N (480 mL; 3.36 mol) and the mixture was stirred at 100°C in steel bomb for 16 h. The mixture was cooled to RT and the solvant was evaporated under reduced pressure. iPr20 was added to the residue and the solid was filtered. The filtrate was evaporated to dryness and the crude was purified by preparative LC on (Irregular SiOH 20-45??? 1000g DAVISIL). Mobile phase (0.5percent NH4OH, 94percent DCM, 6percent MeOH). The pure fraction was collected and evaporated to give 4.9 g of intermediate J-1 a as a brown oil (65percent yield). 1 H NMR (DMSO-de, 400MHz) : ? (ppm) 8.60 (br. s., 1 H), 7.58 (s, 1 H), 6.76 (s, 1 H), 1 .85 (m, 1 H), 0.86 (m, 2H), 0.71 (m, 2H).

Reference： [1]Patent: WO2013/68438,2013,A1 .Location in patent: Page/Page column 16

8
[ 38956-79-5 ]
[ 1489-69-6 ]
C₉H₁₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 oC for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 oC for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulphate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7.
	In ethanol; at 60℃; for 0.5h;	General procedure: A mixture of corresponding hydrazinylpyridazine 1 or 5 (1 mmol) and aldehyde 2 (1.1 mmol) in ethanol (5 mL) was heated at 60 C for 0.5 h. The formation of hydrazone was checked by TLC and the reaction mixture was cooled to rt. Oxone (1.5 mmol) was added to the mixture at rt followed by tetramethyl ammonium bromide (0.2 mmol) and the resulting mixture was heated at 60 C for another 5 h. The mixture was cooled to rt and extracted with dichloromethane (2 × 25 mL), dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography using hexane/ethyl acetate as eluent to furnish the desired triazolopyridazines 4 and 7 (See reference no; 7 for supporting information).

Reference： [1]Journal of the Korean Chemical Society,2013,vol. 57,p. 606 - 611
[2]Journal of the Korean Chemical Society,2014,vol. 58,p. 377 - 380

9
[ 7504-94-1 ]
[ 1489-69-6 ]
C₈H₁₀N₄ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 606 - 614

10
[ 59352-90-8 ]
[ 1489-69-6 ]
6-bromo-2-cyclopropyl-5-methyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With cobalt(II) hydroxide; In ethanol;	The <strong>[59352-90-8]2,3-diamino-5-bromo-6-methylpyridine</strong> (250 mg, 1.2 mmol) and cyclopropanecarboxaldehyde (104 mg, 1.45 mmol) was dissolved in 4 ml of ethanol and cobalt hydroxide (12 mg, 0.12 mmol) blended. The reaction mixture was concentrated to dryness under reduced pressure. The residue was by chromatography via Biotage Isolem (SNAP 25, had hospital / ethyl acetate gradient) to be purified. This produced 207 mg (theoretical value of 66percent value) subject compound.

Reference： [1]Patent: TW2016/5809,2016,A .Location in patent: Page/Page column 70

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Isomers

Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Halogenation ? Hantzsch Dihydropyridine Synthesis ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 1489-69-6 ]

Aldehydes

[ 96-17-3 ]

2-Methylbutyraldehyde

Similarity: 0.85

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[ CAS No. 1489-69-6 ] {[proInfo.proName]}

Quality Control of [ 1489-69-6 ]

Related Doc. of [ 1489-69-6 ]

Product Details of [ 1489-69-6 ]

Calculated chemistry of [ 1489-69-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1489-69-6 ]

Application In Synthesis of [ 1489-69-6 ]

[ 1489-69-6 ] Synthesis Path-Upstream 1~1

[ 1489-69-6 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 1489-69-6 ]

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1489-69-6 ]