15963-40-3|Methyl 3-methylenecyclobutanecarboxylate| Ambeed

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Quality Control of [ 15963-40-3 ] Purity: 95% (stabilized with MEHQ) SDS Specification

COA

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NMR

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Product Details of [ 15963-40-3 ]

CAS No. :	15963-40-3
Formula :	C₇H₁₀O₂
M.W :	126.15
SMILES Code :	COC(=O)C1CC(=C)C1
MDL No. :	MFCD01087180
InChI Key :	OSWTXCSCDKIANQ-UHFFFAOYSA-N
Pubchem ID :	11051654

Safety of [ 15963-40-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 15963-40-3 ]

* 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 [ 15963-40-3 ]

[ 15963-40-3 ] Synthesis Path-Downstream 1~42

1
[ 463-49-0 ]
[ 292638-85-8 ]
[ 15963-40-3 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 2723,2725.

2
[ 186581-53-3 ]
[ 15760-35-7 ]
[ 15963-40-3 ]

References: [1]Journal of the American Chemical Society,1970,vol. 92,p. 3688 - 3696.

3
[ 186581-53-3 ]
[ 10555-42-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

4
[ 186581-53-3 ]
[ 15760-36-8 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.

5
[ 67-56-1 ]
[ 15963-40-3 ]
[ 5119-74-4 ]

References: [1]Tetrahedron,1965,vol. 21,p. 2749 - 2769.

6
[ 917-64-6 ]
[ 15963-40-3 ]
[ 29555-06-4 ]

References: [1]Journal of the American Chemical Society,1970,vol. 92,p. 3688 - 3696.

7
[ 15963-40-3 ]
[ 14924-54-0 ]

References: [1]Journal of Organic Chemistry,1967,vol. 32,p. 3950 - 3955.

8
[ 15963-40-3 ]
[ 10555-45-0 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

9
[ 15963-40-3 ]
[ 89892-95-5 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

10
[ 15963-40-3 ]
[ 695-95-4 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.

11
[ 89892-95-5 ]
[ 30493-92-6 ]
[ 15963-40-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 777 - 778.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 870.

12
[ 89892-95-5 ]
[ 15963-40-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 777 - 778.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 870.

13
[ 15963-40-3 ]
1-Oxa-spiro[2.3]hexane-5-carboxylic acid methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1142.
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1251.

16
[ 67-56-1 ]
[ 15963-40-3 ]
methyl trans-3-bromomethyl-3-methoxycyclobutane-1-carboxylate [ No CAS ]
methyl cis-3-bromomethyl-3-methoxycyclobutane-1-carboxylate [ No CAS ]
methyl cis-3-bromo-3-methoxymethylcyclobutane-1-carboxylate [ No CAS ]
methyl trans-3-bromo-3-methoxymethylcyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

17
[ 15963-40-3 ]
[ 578715-80-7 ]
[ 578715-81-8 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

18
[ 15963-40-3 ]
methyl cis-3-bromo-3-bromomethylcyclobutane-1-carboxylate [ No CAS ]
methyl trans-3-bromo-3-bromomethylcyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

19
[ 15963-40-3 ]
[ 578715-77-2 ]
[ 578715-76-1 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

20
[ 15963-40-3 ]
ethyl nitrodiazoacetic ester [ No CAS ]
1-nitro-spiro[2.3]hexane-1,5-dicarboxylic acid 1-ethyl ester 5-methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 8241 - 8244.

21
[ 15963-40-3 ]
1-amino-spiro[2.3]hexane-1,5-dicarboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 8241 - 8244.

22
[ 15963-40-3 ]
methyl 3-hydroxymethylbicyclo[1.1.0]butane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[3]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[4]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[5]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1142.
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1251.

23
[ 15963-40-3 ]
methyl 3-bromomethylenecyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

24
[ 15963-40-3 ]
methyl 3-bromomethylbicyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

25
[ 15963-40-3 ]
[ 578715-80-7 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

26
[ 15963-40-3 ]
[ 578715-81-8 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

27
[ 15963-40-3 ]
N,N-diisopropyl-3-hydroxymethylbicyclobutane-1-carboxamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

28
[ 15963-40-3 ]
[ 89580-49-4 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

29
[ 15963-40-3 ]
[ 10555-43-8 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

30
[ 15963-40-3 ]
[ 311-75-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

31
[ 15963-40-3 ]
(3-methylenecyclobutyl)methyl-4-methylbenzenesulfonate [ No CAS ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

32
[ 15963-40-3 ]
[ 10555-46-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

33
[ 15963-40-3 ]
[ 10555-48-3 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

34
[ 15963-40-3 ]
[ 10555-42-7 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

35
[ 15760-35-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.
[2]Patent: WO2012/154204,2012,A1 .
[3]Patent: WO2015/66413,2015,A1 .
[4]Patent: WO2015/129926,2015,A1 .
[5]Patent: WO2015/180612,2015,A1 .
[6]Patent: WO2015/196071,A1 .
Patent: ,2015, .
[7]Patent: WO2016/105468,2016,A1 .
[8]Patent: CN105566324,2016,A .
[9]Patent: WO2016/115090,2016,A1 .
[10]Patent: WO2017/40606,2017,A1 .
[11]Patent: WO2018/69863,2018,A1 .
[12]Patent: WO2018/229629,2018,A1 .
[13]Patent: WO2019/63748,2019,A1 .

36
[ 408326-43-2 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

37
[ 5164-23-8 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

38
[ 5164-22-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

39
diethyl[nitro(diazo)methyl]phosphonate [ No CAS ]
[ 15963-40-3 ]
[ 1219792-02-5 ]

References: [1]Synthesis,2010,p. 259 - 266.

40
[ 75-11-6 ]
[ 15963-40-3 ]
[ 1383823-60-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a solution of Et2Zn (11.89 mL, 11.89 mmol) in DCM (10 mL) was added a solution of TFA (0.88 mL, 11.89 mmol) in DCM (10 mL) dropwise at 0 C for 30 minutes. A solution of CH2I2 (0.96 mL, 11.89 mmol) in DCM (10 mL) was added dropwise at 0 C for 45 minutes. The reaction mixture was stirred at 0 C for 1 hour. A solution of methyl 3- methylenecyclobutanecarboxylate (500 mg, 3.96 mmol) in DCM (5 mL) was added to the reaction mixture. The reaction mixture was allowed to warm to 15 C for 16 hours. Saturated NH4CI solution (50 mL) was added to the reaction mixture and the mixture was extracted with DCM (50 mL c 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by silica gel column chromatography (10 % EtOAc in petroleum ether) to afford the title compound (400 mg, 72 %) as a yellow oil. ' H NMR (400 MHz, CDCl3) d 3.71 (s, 3H), 3.34 - 3.27 (m, 1H), 2.53 - 2.48 (m, 2H), 2.26 - 2.20 (m, 2H), 0.49 - 0.42 (m, 4H).
63%		To a solution of diethylzinc (1.0 M in hexane, 46 mL, 46 mmol) in DCM (200 mL) was added a solution of TFA (3.54 mL, 46 mmol) in DCM (50 mL) dropwise at 0 C for 30 min. A solution of diiodomethane (3.7 mL, 46 mmol) in DCM (50 mL) was added dropwise at 0 C for 45 min. The mixture was stirred at the same temperature for 1 h. A solution of compound A141-2 (2.52 g, 20 mmol) in DCM (30 mL) was added to the reaction mixture. The mixture was allowed to warm to room temperature for overnight. The reaction mixture was quenched with saturated NH4C1 aq. (200 mL) and extracted with DCM. The collected organic layer was dried over MgS04 and concentrated under reduced pressure. The residue was purified by silicagel chromatography (20% EtOAc/hexane as eluent) to provide compound Al 41-3 (1.77 g, 63%) as a colorless oil.
		A cold (0C) solution of diethyl zinc (79.3 mL, 1.0 M in Hexanes) in dichloromethane (66 mL) was treated with the dropwise addition of TFA (6.11 mL, 79.3 mL) in dichloromethane (27 mL). After 1 hour of stirring, diiodomethane (6.39 mL, 79.3 mmol) in dichloromethane (27 mL) was then introduced. After 40 min, I-13A (4.00 g, 31.7 mmol) dichloromethane (10 mL) was added dropwise. The reaction was left to stir for 2 hours and then quenched with sat'd NH4CI (aq.). Phases were separated and the organic phase collected, dried (MgS04), filtered, concentrated, and distilled (42-44C, 0.1 mmHg) to afford the desired spirocycle. (400 MHz, CDC13) delta 3.69 (s, 3H), 3.28 (m, 1H), 2.49 (m, 2H), 2.22 (m, 2H), 0.43 (m, 4H); MS m/z 141.1 (M + 1).

1.9 g

Description 67Methyl spiroL2.3]hexane-5-carboxylate (D67)To an ice-cooled (0C) solution of diethylzinc (1.0 M in hexane) (39.6 mL) in DCM (30 mL) was added dropwise a solution of TFA (3.05 mL) in DCM (10 mL). After one hour of stirring, diiodomethane (10.62 g) in DCM (10 mL) was then introduced. After 40 mm, the solution of methyl 3-methylene cyclobutanecarboxylate (D66, 2.0 g) in DCM (4 mL) was added dropwise. Thereaction was stirred at RT for 2 hours and then quenched with saturated NH4C1 solution (30 mL).The organic layer was separated, dried and concentrated to afford the title compound (1.9 g) as paleyellow oil. MS (ESI): C8H1202 requires 140; found 139 [M-H].

References: [1]Patent: WO2020/51099,2020,A1 .Location in patent: Paragraph 0660-0663.
[2]Patent: WO2015/129926,2015,A1 .Location in patent: Page/Page column 109.
[3]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 104.
[4]Patent: WO2015/180612,2015,A1 .Location in patent: Page/Page column 60.

41
[ 67-56-1 ]
[ 15760-36-8 ]
[ 15963-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diazomethyl-trimethyl-silane; In hexanes; dichloromethane; at 0℃; for 0.5h;	A cold (0C) solution of 3- methylenecyclobutanecarboxylic acid (WO2007/063391, 6.07 g, 54.1 mmol) indichloromethane (180 mL) and methanol (18 mL) was treated with the dropwise addition of (trimethylsilyl)diazomethane (28.4 mL, 2.0 M in Hexanes). After 30 min, 1 mL of cone. HOAc was added and the reaction concentrated in vacuo. (400 MHz, CDC13) delta 4.78 (m, 2H), 3.67 (s, 3H), 3.10 (m, 1H), 2.98 (m, 2H), 2.88 (m, 2H); MS m/z 127.1 (M + 1).

References: [1]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 104.

42
[ 15963-40-3 ]
[ 1383823-62-8 ]

References: [1]Patent: WO2012/87519,2012,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Halogenation • Heat of Combustion • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 15963-40-3 ]

Alkenyls

A161969 [145576-28-9]

Ethyl 4-methylenecyclohexanecarboxylate

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A163285 [40637-56-7]

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Aliphatic Cyclic Hydrocarbons

A161969 [145576-28-9]

Ethyl 4-methylenecyclohexanecarboxylate

Similarity: 0.88

A285859 [56124-48-2]

6-(Methoxycarbonyl)cyclohex-3-enecarboxylic acid

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Esters

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Similarity: 0.88

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 15963-40-3

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