7149-18-0|Ethyl 2-aminocyclopent-1-enecarboxylate| Ambeed

CAS No. :	7149-18-0
Formula :	C₈H₁₃NO₂
M.W :	155.19
SMILES Code :	NC1=C(C(OCC)=O)CCC1
MDL No. :	MFCD00216929
InChI Key :	FMEHILPGLKGSCA-UHFFFAOYSA-N
Pubchem ID :	243333

Safety of [ 7149-18-0 ]

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

Application In Synthesis of [ 7149-18-0 ]

* 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 [ 7149-18-0 ]

[ 7149-18-0 ] Synthesis Path-Downstream 1~54

1
[ 7149-18-0 ]
[ 108-24-7 ]
[ 29942-18-5 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2487,2489.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 9570 - 9571.
[3]Organic Process Research and Development,2008,vol. 12,p. 1253 - 1260.

2
[ 611-10-9 ]
[ 7149-18-0 ]

References: [1]Synthetic Communications,2004,vol. 34,p. 909 - 916.
[2]New Journal of Chemistry,2005,vol. 29,p. 769 - 772.
[3]Green Chemistry,2020,vol. 22,p. 136 - 143.
[4]Bulletin des Societes Chimiques Belges,1995,vol. 104,p. 387 - 392.
[5]Helvetica Chimica Acta,1945,vol. 28,p. 1684,1690.
[6]Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 104.
[7]Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 104.
[8]Journal of the Chemical Society,1960,p. 2119 - 2132.
[9]Journal of Organic Chemistry,1978,vol. 43,p. 1460 - 1462.
[10]Journal of the American Chemical Society,2003,vol. 125,p. 9570 - 9571.
[11]Organic Process Research and Development,2008,vol. 12,p. 1253 - 1260.
[12]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1113 - 1118.

3
[ 7149-18-0 ]
[ 103-71-9 ]
[ 5313-47-3 ]

References: [1]Archives of Biochemistry,1959,vol. 83,p. 141,148.

4
[ 7149-18-0 ]
[ 556-61-6 ]
[ 108989-50-0 ]

References: [1]Archives of Biochemistry,1959,vol. 83,p. 141,148.

5
[ 7149-18-0 ]
[ 105-53-3 ]
[ 55618-82-1 ]

References: [1]Helvetica Chimica Acta,1945,vol. 28,p. 1684,1690.

6
[ 7149-18-0 ]
[ 104743-69-3 ]

References: [1]Journal of the Chemical Society,1960,p. 2119 - 2132.

7
[ 7149-18-0 ]
[ 621-29-4 ]
2-(3-m-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

8
[ 7149-18-0 ]
[ 104-12-1 ]
2-[3-(4-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

9
[ 7149-18-0 ]
[ 103-71-9 ]
[ 49786-25-6 ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

10
[ 7149-18-0 ]
[ 622-58-2 ]
2-(3-p-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

11
[ 7149-18-0 ]
[ 614-68-6 ]
2-(3-o-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

12
[ 7149-18-0 ]
[ 2909-38-8 ]
2-[3-(3-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

14
[ 19975-56-5 ]
[ 7149-18-0 ]
2,3,7,8-tetrahydro-5H,6H-cyclopenta[1,2-d]thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 743 - 747.

15
[ 20112-79-2 ]
[ 7149-18-0 ]
1,2,3,6,7,8-hexahydro-5H-cyclopenta[1,2-d]imidazo[1,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 743 - 747.

16
[ 58842-19-6 ]
[ 7149-18-0 ]
2,3,4,7,8,9-hexahydro-6H-cyclopenta[4',3':4,5]pyrimido[2,1-b][1,3]thiazin-6-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 743 - 747.

17
[ 20112-81-6 ]
[ 7149-18-0 ]
2,3,4,7,8,9-hexahydro-1H,6H-cyclopenta[1,2-d]pyrimido[1,2-a]pyrimidin-6-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 743 - 747.

18
[ 7149-18-0 ]
[ 24066-82-8 ]
ethyl 2-[3-ethoxycarbonylmethylthioureido]cyclopentene-1-carboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 391 - 395.

19
[ 7149-18-0 ]
[ 2949-22-6 ]
ethyl 2-[3-ethoxycarbonylmethylureido]cyclopentene-1-carboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 391 - 395.

20
[ 7149-18-0 ]
cis-2-acetylaminocyclopentanecarboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 9570 - 9571.
[2]Organic Process Research and Development,2008,vol. 12,p. 1253 - 1260.

21
[ 7149-18-0 ]
3-ethoxycarbonylmethyl-2,4-dioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 391 - 395.

22
[ 7149-18-0 ]
3-ethoxycarbonylmethyl-4-oxo-2-thioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 391 - 395.

23
[ 7149-18-0 ]
[ 5313-47-3 ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

24
[ 7149-18-0 ]
3-p-Tolyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

25
[ 7149-18-0 ]
3-m-Tolyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

26
[ 7149-18-0 ]
3-(3-Chloro-phenyl)-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

27
[ 7149-18-0 ]
3-(4-Chloro-phenyl)-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

28
[ 7149-18-0 ]
3-o-Tolyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione [ No CAS ]

References: [1]Heterocycles,1983,vol. 20,p. 2233 - 2235.

30
[ 7149-18-0 ]
(+/-)-<i>trans</i>-octahydro[1]pyrindine [ No CAS ]

References: [1]Helvetica Chimica Acta,1945,vol. 28,p. 1684,1690.

31
[ 7149-18-0 ]
[ 56946-65-7 ]

References: [1]Helvetica Chimica Acta,1945,vol. 28,p. 1684,1690.

32
[ 7149-18-0 ]
[ 55618-81-0 ]

References: [1]Helvetica Chimica Acta,1945,vol. 28,p. 1684,1690.

33
[ 7149-18-0 ]
[ 114986-36-6 ]

References: [1]Archives of Biochemistry,1959,vol. 83,p. 141,148.

34
[ 7149-18-0 ]
[ 18227-17-3 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2487,2489.

35
[ 7149-18-0 ]
[ 49786-34-7 ]

References: [1]Archives of Biochemistry,1959,vol. 83,p. 141,148.

36
[ 7149-18-0 ]
[ 933775-94-1 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2487,2489.

37
[ 7149-18-0 ]
[ 18227-16-2 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 2487,2489.

38
[ 141-28-6 ]
[ 7149-18-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 104.

39
[ 20873-66-9 ]
[ 7149-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol;	Part B A solution containing ethyl 2-[(ethoxycarbonyl)-amino]-1-cyclopentene-1-carboxylate (72 g, 0.32 moles) and 25 wt % sodium methoxide in methanol (91.5 mL, 0.40 moles) was refluxed for about 18 hours. Methanol (200 mL) was added during the course of the reaction. The reaction mixture was allowed to cool to ambient temperature then diluted with water and extracted with diethyl ether (5*100 mL). The ether extracts were combined, treated with activated charcoal, dried over sodium sulfate then evaporated to provide 43.8 g of ethyl 2-amino-1-cyclopentene-1-carboxylate as an ivory solid, m.p. 90-92 C.

References: [1]Patent: US5352784,1994,A .

40
[ 7149-18-0 ]
[ 39619-07-3 ]
methyl 3-oxo-3-[(2-ethoxycarbonylcyclopenten-1-yl)amino]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	Part C Ethyl 2-amino-1-cyclopentene-1-carboxylate (43.8 g, 0.28 moles) was combined with triethyl amine (42.9 mL, 0.31 moles) and methylene chloride (850 mL) and cooled to 0 C. Methyl malonyl chloride (33.4 mL, 0.31 mole) was added dropwise to the reaction mixture. After the addition the reaction was stirred for about 1 hr at 0 C. The reaction mixture was quenched with water (500 mL). The layers were separated. The aqueous layer was extracted with methylene chloride (4*100 mL). The organic layers were combined, dried over magnesium sulfate and evaporated under vacuum to provide 56.2 g of an oil. The oil was purified by silica gel chromatography eluding with hexane:ethyl acetate (70:30) to provide 46 g of methyl 3-oxo-3-[(2-ethoxycarbonylcyclopenten-1-yl)amino]propanoate as a clear oil.

References: [1]Patent: US5352784,1994,A .

41
[ 628-20-6 ]
[ 105-36-2 ]
[ 7149-18-0 ]
pyrrolidin-2-ylideneacetic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 1560 - 1565.
[2]Synthesis,2012,vol. 44,p. 1809 - 1817.

42
[ 628-20-6 ]
[ 105-36-2 ]
[ 7149-18-0 ]
[ 35150-22-2 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 1560 - 1565.
[2]Journal of Organic Chemistry,2012,vol. 77,p. 1560 - 1565.

43
[ 105-36-2 ]
[ 5332-06-9 ]
[ 7149-18-0 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 1560 - 1565.

44
[ 7149-18-0 ]
(+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid hydrochloride [ No CAS ]

References: [1]Organic Process Research and Development,2008,vol. 12,p. 1253 - 1260.

45
[ 7149-18-0 ]
N-(2-(hydroxymethyl)cyclopentyl)-4-methylbenzenesulfonamide [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1113 - 1118.

46
[ 7149-18-0 ]
ethyl cis-2-amino-1-cyclopentane-carboxylate [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1113 - 1118.

47
[ 7149-18-0 ]
ethyl 2-((4-methylphenyl)sulfonamido)cyclopentane-1-carboxylate [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1113 - 1118.

48
[ 7149-18-0 ]
(cis)-1-tosylhexahydrocyclopenta[d]imidazol-2(1H)-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1113 - 1118.

49
[ 32415-91-1 ]
[ 7149-18-0 ]
2-(5-fluorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium tert-butylate; In 1,3,5-trimethyl-benzene; at 150℃; for 4h;	4a) 2-(5-Fluorothiophen-2-yl)-6.7-dihydro-5H-cyclopentafdlpyrimidin-4-ol Potassium tert-butylate (1.34 g, 12 mmol) was added to a solution of 5-fluorothiophene-2- carbonitrile ( 1.52 g, 12 mmol) and ethyl 2-aminocyclopent- l -enecarboxylate ( 1.55 g, 10 mmol) in mesitylene (50 ml) and the mixture was stirred at 150 C for 4 h. 1 N hydrochloric acid ( 12 ml) was then added and the solid which had precipitated out was filtered off, washed with ethyl acetate and dried. Beige-coloured solid. Yield: 1 .3 g (55 % of theory) LC-MS (method 1 ): R, = 3.42 min, m/z: [M+H]+ = 237.2 -NMR (400 MHz, DMSO-d6, 8 ppm): 1.97 (m, 2H), 2.64 (m, 2H), 2.76 (m, 2H), 6.86 (dd, J = 2.0, 4.3, 1 H), 7.88 (s, 1 H), 12.67 (s, 1 H)

References: [1]Patent: WO2014/170020,2014,A1 .Location in patent: Page/Page column 47.

50
[ 32415-91-1 ]
[ 7149-18-0 ]
4-chloro-2-(5-fluorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine [ No CAS ]

References: [1]Patent: WO2014/170020,2014,A1 .

51
[ 7149-18-0 ]
[ 98-59-9 ]
ethyl 2-((4-methylphenyl)sulfonamido)cyclopent-1-ene-1-carboxylate [ No CAS ]

References: [1]Green Chemistry,2020,vol. 22,p. 136 - 143.
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 12167 - 12170.
Angew. Chem.,2018,vol. 130,p. 12344 - 12348,5.

52
[ 7149-18-0 ]
ethyl 2-((N-(3-bromopropyl)-4-methylphenyl)sulfonamido)cyclopent-1-ene-1-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12167 - 12170.
Angew. Chem.,2018,vol. 130,p. 12344 - 12348,5.
[2]Green Chemistry,2020,vol. 22,p. 136 - 143.

53
[ 7149-18-0 ]
ethyl 2-(3-((4-methylphenyl)sulfonamido)propyl)cyclopent-1-ene-1-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 12167 - 12170.
Angew. Chem.,2018,vol. 130,p. 12344 - 12348,5.
[2]Green Chemistry,2020,vol. 22,p. 136 - 143.

54
[ 7149-18-0 ]
C₁₇H₁₃FN₂O₄ [ No CAS ]
C₂₅H₂₆FN₃O₆ [ No CAS ]

References: [1]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 9254 - 9264.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Halogenation • Heat of Combustion • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Related Functional Groups of
[ 7149-18-0 ]

Alkenyls

A248109 [1128-00-3]

Ethyl 2-aminocyclohex-1-enecarboxylate

Similarity: 0.96

A296372 [52909-60-1]

Methyl 2-aminocyclopent-1-enecarboxylate

Similarity: 0.96

Aliphatic Cyclic Hydrocarbons

A248109 [1128-00-3]

Ethyl 2-aminocyclohex-1-enecarboxylate

Similarity: 0.96

A296372 [52909-60-1]

Methyl 2-aminocyclopent-1-enecarboxylate

Similarity: 0.96

Esters

A248109 [1128-00-3]

Ethyl 2-aminocyclohex-1-enecarboxylate

Similarity: 0.96

A296372 [52909-60-1]

Methyl 2-aminocyclopent-1-enecarboxylate

Similarity: 0.96

Amines

A248109 [1128-00-3]

Ethyl 2-aminocyclohex-1-enecarboxylate

Similarity: 0.96

A296372 [52909-60-1]

Methyl 2-aminocyclopent-1-enecarboxylate

Similarity: 0.96

Precautionary Statements-General
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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.: 7149-18-0

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