[ CAS No. 71441-76-4 ] {[proInfo.proName]}

Name: 71441-76-4|Ethyl 1-methylcyclopropanecarboxylate|95%
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SKU: A746622
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Quality Control of [ 71441-76-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 71441-76-4 ]

SDS Specification

Alternatived Products of [ 71441-76-4 ]

Product Details of [ 71441-76-4 ]

CAS No. :	71441-76-4	MDL No. :	MFCD00001284
Formula :	C₇H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IZPYNZLFBUQGCZ-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	544234
Synonyms :

Calculated chemistry of [ 71441-76-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.67
TPSA :	26.3 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) :	-6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	1.3
Log Po/w (WLOGP) :	1.29
Log Po/w (MLOGP) :	1.23
Log Po/w (SILICOS-IT) :	1.66
Consensus Log Po/w :	1.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.26
Solubility :	7.11 mg/ml ; 0.0555 mol/l
Class :	Very soluble
Log S (Ali) :	-1.45
Solubility :	4.52 mg/ml ; 0.0353 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.53
Solubility :	3.8 mg/ml ; 0.0296 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.29

Safety of [ 71441-76-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P270-P301+P312-P330	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 71441-76-4 ]

* 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 [ 71441-76-4 ]
Downstream synthetic route of [ 71441-76-4 ]

[ 71441-76-4 ] Synthesis Path-Upstream 1~7

1
[ 71441-76-4 ]
[ 15910-91-5 ]

Reference： [1] Journal of the American Chemical Society, 1959, vol. 81, p. 1660,1665

2
[ 4606-07-9 ]
[ 74-88-4 ]
[ 71441-76-4 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 16, p. 6030 - 6032
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 2, p. 256 - 260

3
[ 70786-83-3 ]
[ 71441-76-4 ]

Reference： [1] Journal of the American Chemical Society, 1959, vol. 81, p. 1660,1665

4
[ 97-63-2 ]
[ 71441-76-4 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1983, # 23, p. 1446 - 1447

5
[ 29820-55-1 ]
[ 7452-79-1 ]
[ 539-82-2 ]
[ 14924-53-9 ]
[ 71441-76-4 ]

Reference： [1] Liebigs Annalen der Chemie, 1985, # 7, p. 1485 - 1491

6
[ 71441-76-4 ]
[ 6914-76-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: at 50 - 60℃; for 5 h;	Add l-hydroxy-4-nitroisoquinoline (880.3 mmol; 167.4 grams) and POCl₃ (4.95 mol; 460 mL) to a 2 L flask with N₂ inlet, condenser, and thermocouple. Heat the resulting slurry to 100 ⁰C for approximately 1 hour. Concentrate the reaction mixture to dryness using a rotary evaporator. Slurry the residue in 1,2- dichloroethane (402 mL) and cool to 15 ⁰C. Add /-PrOH (1015 mL) drop wise while maintaining a pot temperature of less than 30 ⁰C. Stir the reaction mixture for 2 hours at 20 ⁰C and 1 hour at 10 ⁰C. Filter the reaction mixture, and rinse the cake with isopropyl alcohol (100 mL). Dry under reduced pressure at 50 ⁰C. Yield = 118.5 grams (65percent). Add 1-methyl-cyclopropanecarboxylic acid ethyl ester (405.0 g, 3.16 moles), 5 N sodium hydroxide (1.0 L, 5.00 moles), and methanol (400.0 mL, 9.88 moles) to a 3 L three-necked round-bottom flask. Heat the reaction mixture between 50 ⁰C to 60 ⁰C for 5 hours, then allow to cool to ambient temperature overnight. Remove the organic solvent and extract the basic solution with MTBE (2 x 500 mL). Adjust the pH of the aqueous solution to pH 1 using 600 mL cone. HCl and extract with MTBE (4 x 500 mL). Combine the organic layers, wash with saturate aq. sodium chloride, dry over magnesium sulfate, filter, and remove solvent under reduced pressure. Allow residue to solidify, then add 100 mL heptane and stir the resulting slurry at 0-5° C. Filter the slurry, then dry the resulting solid dried under reduced pressure. Concentrate the filtrate and cooled in an ice bath to afford additional white solid material. Combine to recover 265 g (84percent) of 1-methyl-cyclopropanecarboxylic acid as a white solid.

Reference： [1] Patent: WO2007/53346, 2007, A1, . Location in patent: Page/Page column 21
[2] Journal of the American Chemical Society, 2013, vol. 135, # 16, p. 6030 - 6032

7
[ 71441-76-4 ]
[ 72790-89-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate In toluene	Reference Example 2 Preparation of 1-methyl-1-cyclopropanecarbohydrazide: A mixture of ethyl 1-methyl-1-cyclopropanecarboxylate (10 g, 7.8 mmole) and hydrazine monohydrate (5.1 g, 0.1 mole) is heated with stirring at 100° C. for 4 hours. To the reaction solution is added toluene (50 ml), and the mixture is refluxed for 3 hours while distilling off water. After cooling, the precipitated crystals are collected by filtration, and washed with diisopropyl ether to give the desired compound (8.9 g) as a colorless crystal. Yield: 99percent m.p. 85°-87° C.

Reference： [1] Patent: US5367078, 1994, A,

[ 71441-76-4 ] Synthesis Path-Downstream 1~36

1
3-methyl-4,5-dihydro-3<i>H</i>-pyrazole-3-carboxylic acid ethyl ester [ No CAS ]
[ 80-59-1 ]
[ 71441-76-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1932,vol. 496,p. 280

2
[ 70786-83-3 ]
[ 71441-76-4 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 1660,1665

3
[ 71441-76-4 ]
[ 15910-91-5 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 1660,1665

4
[ 71441-76-4 ]
[ 7452-79-1 ]
[ 3938-95-2 ]

Reference： [1]Liebigs Annalen der Chemie,1985,p. 1485 - 1491

5
[ 29820-55-1 ]
[ 7452-79-1 ]
[ 539-82-2 ]
[ 14924-53-9 ]
[ 71441-76-4 ]

Reference： [1]Liebigs Annalen der Chemie,1985,p. 1485 - 1491

6
2,4-Dichloro-2-methyl-butyric acid ethyl ester [ No CAS ]
[ 71441-76-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1983,p. 1446 - 1447

Yield	Reaction Conditions	Operation in experiment
		Examples of cyclopropanecarboxylic acid esters which can be made according to the invention includes methyl cyclopropanecarboxylate, ethyl cyclopropanecarboxylate, methyl 1-methylcyclopropanecarboxylate, ethyl 1-methylcyclopropanecarboxylate, methyl 1,2-dimethylcyclopropanecarboxylate, ethyl 1,2-dimethylcyclopropanecarboxylate, methyl 1,2,3-trimethylcyclopropanecarboxylate ethyl 1,2,3-trimethylcyclopropanecarboxylate, methyl 2-methylcyclopropanecarboxylate, ...

8
3-methyl-Δ¹-pyrazoline-carboxylic acid-(3)-ethyl ester [ No CAS ]
[ 5837-78-5 ]
[ 71441-76-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1932,vol. 496,p. 280

9
[ 13534-99-1 ]
[ 71441-76-4 ]
[ 634202-30-5 ]

Reference： [1]Synthesis,2003,p. 2033 - 2040

10
[ 71441-76-4 ]
2-(1-methylcyclopropyl)[1,3]oxazolo[4,5-b]pyridine [ No CAS ]

Reference： [1]Synthesis,2003,p. 2033 - 2040

11
[ 71441-76-4 ]
[ 634202-38-3 ]

Reference： [1]Synthesis,2003,p. 2033 - 2040

12
[ 97-63-2 ]
[ 71441-76-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1983,p. 1446 - 1447

13
petroleum ether-dichloromethane [ No CAS ]
[ 71441-76-4 ]
N-<imino(cyclopropylamino)methyl>-4-morpholinecarboximidamide hydrochloride [ No CAS ]
[ 148312-58-7 ]

Yield	Reaction Conditions	Operation in experiment
17%	With sodium; In ethanol; water;	1. 2-Cyclopropylamino-4-(1-methylcylopropyl)-6-morpholino-1,3,5-triazine (compound 24). 0.48 g (20 mmoles) of sodium is dissolved in 20 ml of anhydrous ethanol. This solution is added to an ethanol solution containing 2.48 g (10 mmoles) of N-[imino(cyclopropylamino)methyl]-4-morpholinecarboximidamide hydrochloride, and 2.82 g (22 mmoles) of <strong>[71441-76-4]ethyl 1-methylcyclopropane-carboxylate</strong> are then also added to the mixture. The mixture is then heated under reflux under nitrogen for 88 hours. It is cooled, the alcohol is evaporated under reduced pressure and the residue is redissolved in 50 ml of water and 200 ml of dichloromethane. The aqueous phase is separated off and the organic phase is washed twice with 50 ml of water and dried over magnesium sulfate. The solvent is evaporated under reduced pressure and the residue is recrystallized from a 1:1 (v/v) mixture of petroleum ether-dichloromethane. 0.49 g of 2-cyclopropylamino-4-(1-methylcyclopropyl)-6-morpholino-1,3,5-triazine is obtained. Yield: 17%. M.P.: 94-95% C. Analysis for C14 H21 N5 O in %: calc.: C 61.06; H 7.69; N 25.44; found: 61.15; 7.66; 25.56.

Reference： [1]Patent: US5258513,1993,A

14
[ 150868-39-6 ]
[ 71441-76-4 ]
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-morpholino-imidazo[1,5-a]quinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-morpholino-imidazo[1,5-a]quinazoline (Compound 71), m.p. 232-236 C., from 5-morpholino-imidazo[1,5-a]quinazoline-3-carboxamide oxime and ethyl 1-methylcyclopropyl carboxylate.

Reference： [1]Patent: US5371080,1994,A

15
[ 71441-76-4 ]
[ 72790-89-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate; In toluene;	Reference Example 2 Preparation of 1-methyl-1-cyclopropanecarbohydrazide: A mixture of <strong>[71441-76-4]ethyl 1-methyl-1-cyclopropanecarboxylate</strong> (10 g, 7.8 mmole) and hydrazine monohydrate (5.1 g, 0.1 mole) is heated with stirring at 100° C. for 4 hours. To the reaction solution is added toluene (50 ml), and the mixture is refluxed for 3 hours while distilling off water. After cooling, the precipitated crystals are collected by filtration, and washed with diisopropyl ether to give the desired compound (8.9 g) as a colorless crystal. Yield: 99percent m.p. 85°-87° C.

Reference： [1]Patent: US5367078,1994,A

16
[ 71441-76-4 ]
[ 6914-76-7 ]

Yield	Reaction Conditions	Operation in experiment
84%		Add l-hydroxy-4-nitroisoquinoline (880.3 mmol; 167.4 grams) and POCl3 (4.95 mol; 460 mL) to a 2 L flask with N2 inlet, condenser, and thermocouple. Heat the resulting slurry to 100 0C for approximately 1 hour. Concentrate the reaction mixture to dryness using a rotary evaporator. Slurry the residue in 1,2- dichloroethane (402 mL) and cool to 15 0C. Add /-PrOH (1015 mL) drop wise while maintaining a pot temperature of less than 30 0C. Stir the reaction mixture for 2 hours at 20 0C and 1 hour at 10 0C. Filter the reaction mixture, and rinse the cake with isopropyl alcohol (100 mL). Dry under reduced pressure at 50 0C. Yield = 118.5 grams (65%). Add <strong>[71441-76-4]1-methyl-cyclopropanecarboxylic acid ethyl ester</strong> (405.0 g, 3.16 moles), 5 N sodium hydroxide (1.0 L, 5.00 moles), and methanol (400.0 mL, 9.88 moles) to a 3 L three-necked round-bottom flask. Heat the reaction mixture between 50 0C to 60 0C for 5 hours, then allow to cool to ambient temperature overnight. Remove the organic solvent and extract the basic solution with MTBE (2 x 500 mL). Adjust the pH of the aqueous solution to pH 1 using 600 mL cone. HCl and extract with MTBE (4 x 500 mL). Combine the organic layers, wash with saturate aq. sodium chloride, dry over magnesium sulfate, filter, and remove solvent under reduced pressure. Allow residue to solidify, then add 100 mL heptane and stir the resulting slurry at 0-5 C. Filter the slurry, then dry the resulting solid dried under reduced pressure. Concentrate the filtrate and cooled in an ice bath to afford additional white solid material. Combine to recover 265 g (84%) of 1-methyl-cyclopropanecarboxylic acid as a white solid.

Reference： [1]Patent: WO2007/53346,2007,A1 .Location in patent: Page/Page column 21
[2]Journal of the American Chemical Society,2013,vol. 135,p. 6030 - 6032

17
[ 71441-76-4 ]
[ 100-46-9 ]
[ 1019680-55-7 ]

Reference： [1]Chemical Communications,2008,p. 1100 - 1102

18
[ 4606-07-9 ]
[ 74-88-4 ]
[ 71441-76-4 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 6030 - 6032
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 256 - 260

19
[ 71441-76-4 ]
[ 1429896-62-7 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 6030 - 6032

20
[ 71441-76-4 ]
[ 16480-05-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 6030 - 6032

21
[ 71441-76-4 ]
[ 95924-26-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3436 - 3441

22
[ 71441-76-4 ]
[ 1267856-42-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3436 - 3441

23
[ 71441-76-4 ]
[ 1267851-21-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3436 - 3441

24
[ 71441-76-4 ]
[ 75-05-8 ]
[ 88485-78-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3436 - 3441
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 791 - 796

25
[ 71441-76-4 ]
[ 1422051-50-0 ]