42185-27-3|2-(2-Oxocyclohexyl)acetonitrile| Ambeed

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Structure of 42185-27-3

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Quality Control of [ 42185-27-3 ] Purity: 95% SDS Specification

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Product Details of [ 42185-27-3 ]

CAS No. :	42185-27-3
Formula :	C₈H₁₁NO
M.W :	137.18
SMILES Code :	N#CCC1C(CCCC1)=O
MDL No. :	MFCD18431742
InChI Key :	NDKUZEVDMZDUGK-UHFFFAOYSA-N
Pubchem ID :	543553

Safety of [ 42185-27-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of [ 42185-27-3 ]

* 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 [ 42185-27-3 ]

[ 42185-27-3 ] Synthesis Path-Downstream 1~42

1
[ 1125-99-1 ]
[ 107-14-2 ]
[ 42185-27-3 ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: Following the procedures of Stork,15 the cycloketone and pyrrolidine (1.1equiv) were dissolved in benzene or toluene (300mLmol-1 ketone; toluene for n>1) and refluxed for 5-10h (cyclopentanone and -hexanone) or 24-48h (cycloheptanone and -octanone). Excess pyrrolidine and solvent were removed under reduced pressure and the yellow to brown oily residue was directly used for further reactions. For medium-sized rings a small amount of p-toluenesulfonic acid was added (n>1). (0024) Next, the enamine (typically 5-20g) was dissolved in anhydrous dioxane (400mLmol-1) under an argon atmosphere. Then the electrophile (1.5equiv; chloroacetonitrile for compounds 1, 3, 5 and 7, or acrylonitrile for compounds 2, 4, 6 and 8) was added in one shot using a syringe. Occasionally, more electrophile was added in case of stagnant reactions. The mixture was refluxed for 10-48h until complete conversion of the enamine could be detected by GC-MS. Subsequently, water (200mLmol-1) was added and the biphasic mixture was heated to reflux for 30-60min. Dioxane was then removed by rotary evaporation and the residue was partitioned between EtOAc (2mLmmol-1) and 2N HCl (0.5mLmmol-1). The aqueous phase was extracted with EtOAc (4× same volume as before) and the pooled extracts were dried over sodium sulfate and concentrated under reduced pressure. Purification of the brown crude oils was performed on MPLC or via distillation.

References: [1]Tetrahedron,2016,vol. 72,p. 7241 - 7248.
[2]Journal of the American Chemical Society,1959,vol. 81,p. 3955,3957.
[3]Russian Journal of Organic Chemistry,1994,vol. 30,p. 582 - 589.
Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 546 - 553.

2
[ 769092-24-2 ]
[ 151-50-8 ]
[ 42185-27-3 ]

References: [1]Chemische Berichte,1955,vol. 88,p. 1340,1343.

3
[ 670-80-4 ]
[ 107-14-2 ]
[ 42185-27-3 ]

References: [1]Bollettino Chimico Farmaceutico,1993,vol. 132,p. 472 - 474.

4
[ 42185-27-3 ]
[ 90242-33-4 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 7175 - 7187.
[2]Organic Letters,2020,vol. 22,p. 5176 - 5181.
[3]Bollettino Chimico Farmaceutico,1993,vol. 132,p. 472 - 474.

5
[ 42185-27-3 ]
(1R*,2S*)-2-hydroxycyclohexane acetonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

6
[ 930-68-7 ]
[ 590-17-0 ]
[ 42185-27-3 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 439 - 443.

7
[ 42185-27-3 ]
[ 107-21-1 ]
[ 95192-95-3 ]

References: [1]Synlett,2010,p. 529 - 534.
[2]Russian Journal of Organic Chemistry,1994,vol. 30,p. 582 - 589.
Zhurnal Organicheskoi Khimii,1994,vol. 30,p. 546 - 553.

8
[ 6982-25-8 ]
[ 42185-27-3 ]
2-Cyanomethyl-4',5'-dimethylspiro<cyclohexane-1,2'-<1,3>dioxolane> [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

9
[ 90242-33-4 ]
[ 42185-27-3 ]

References: [1]Organic letters,2000,vol. 2,p. 2873 - 2876.
[2]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.
[3]Synlett,2010,p. 529 - 534.

10
[ 42185-27-3 ]
[ 100-63-0 ]
(R)-(2-Oxocyclohexyl)ethanenitrile phenylhydrazone [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 149 2-oxocyclohexaneacetonitrile STR151 Cyclohexanone is reacted with bromoacetonitrile by the method of Example 65 to generate the title compound.

13
(+-)-cyano-<2-oxo-cyclohexyl>-acetic acid ethyl ester [ No CAS ]
[ 42185-27-3 ]

References: [1]Canadian Journal of Chemistry,1957,vol. 35,p. 663,669.

14
[ 151-50-8 ]
(+-)-2-piperidinomethyl-cyclohexanone [ No CAS ]
[ 42185-27-3 ]

References: [1]Chemische Berichte,1955,vol. 88,p. 1340,1343.

15
[ 7732-18-5 ]
[ 151-50-8 ]
[ 6966-09-2 ]
[ 42185-27-3 ]

References: [1]Chemische Berichte,1955,vol. 88,p. 1340,1343.

16
[ 42185-27-3 ]
[ 4009-98-7 ]
(Z)-[2-(Methoxymethylene)cyclohexyl]acetonitrile [ No CAS ]
(E)-[2-(Methoxymethylene)cyclohexyl]acetonitrile [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 1265 - 1270.

17
[ 42185-27-3 ]
[ 86296-14-2 ]
C₁₆H₂₁NO₄ [ No CAS ]

References: [1]Organic letters,2000,vol. 2,p. 2873 - 2876.

18
[ 17851-97-7 ]
[ 590-17-0 ]
[ 42185-27-3 ]

References: [1]Organic Letters,2001,vol. 3,p. 2591 - 2594.

19
[ 624-75-9 ]
[ 6651-36-1 ]
[ 42185-27-3 ]

References: [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 2049 - 2052.

20
(E)-8-Oxo-oct-2-enenitrile [ No CAS ]
[ 42185-27-3 ]

References: [1]Organic letters,2000,vol. 2,p. 2873 - 2876.

21
[ 38461-13-1 ]
[ 42185-27-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

22
[ 42185-27-3 ]
2-Carboxymethyl-4',5'-dimethylspiro<cyclohexane-1,2'-<1,3>dioxolane> [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

23
[ 81156-45-8 ]
[ 42185-27-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

24
[ 765-87-7 ]
[ 42185-27-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

25
[2,2-Dimethoxy-cyclohex-(E)-ylidene]-acetonitrile [ No CAS ]
[ 42185-27-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

26
[ 173948-39-5 ]
[ 42185-27-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2969 - 2988.

27
[ 42185-27-3 ]
[ 6975-71-9 ]

References: [1]Bollettino Chimico Farmaceutico,1993,vol. 132,p. 472 - 474.

28
[ 42185-27-3 ]
[ 3399-73-3 ]

References: [1]Bollettino Chimico Farmaceutico,1993,vol. 132,p. 472 - 474.

29
[ 42185-27-3 ]
[ 74741-45-0 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

30
[ 42185-27-3 ]
[ 74708-14-8 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

31
[ 42185-27-3 ]
[ 74708-25-1 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

32
[ 42185-27-3 ]
[ 74708-24-0 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

33
[ 42185-27-3 ]
[ 74629-93-9 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

34
[ 42185-27-3 ]
[ 74708-32-0 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

35
[ 42185-27-3 ]
[ 74629-91-7 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

36
[ 42185-27-3 ]
[ 74708-29-5 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

37
[ 42185-27-3 ]
trans-hexahydro-2(3H)-benzofuranone [ No CAS ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

38
[ 42185-27-3 ]
cis-hexahydrobenzofuran-2(3H)-one [ No CAS ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4111 - 4117.

39
[ 42185-27-3 ]
[ 1101905-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water;	EXAMPLE 150 2-(hydroxyimino)cyclohexaneacetonitrile STR152 The product of Example 149 is reacted with hydroxylamine hydrochloride and sodium acetate in ethanol/water by the method of Example 1 to generate the title compound.

References: [1]Patent: US5883251,1999,A .

40
[ 42185-27-3 ]
[ 7440-16-6 ]
[ 120-72-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen;	EXAMPLE IV In the manner described in Example III, a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of rhodium on γ-aluminumoxide (0.5 wt. % Rh). The conversion of the oxonitrile is 99%, and the yields are indole 9%, tetrahydroindole 26% and hexahydroindole 5%.

References: [1]Patent: US4473699,1984,A .

41
[ 42185-27-3 ]
[ 7440-06-4 ]
[ 120-72-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;	EXAMPLE III In the manner described in Example I, but differing in that the temperature of the catalyst and the inert material is kept at 240 C., a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of platinum on γ-aluminumoxide (0.5 wt. % Pt). The oxonitrile conversion is 100%, and the yields are indole 18%, tetrahydroindole 19% and hexahydroindole 1%.

References: [1]Patent: US4473699,1984,A .

42
γ-aluminumoxide [ No CAS ]
[ 42185-27-3 ]
[ 7440-06-4 ]
[ 120-72-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With hydrogen;	EXAMPLE II In the manner described in Example 1, a mixture of 2-oxocyclohexaneacetonitrile and hydrogen is passed over a catalyst composed of platinum and γ-aluminumoxide (0.5 wt. % platinum). The oxonitrile conversion is 69%, and the yields are indole 11%, tetrahydroindole 12% and hexahydroindole 1%.

References: [1]Patent: US4473699,1984,A .

Historical Records

Technical Information

• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Blaise Reaction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Grignard Reaction • Halogenation • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Thorpe-Ziegler Reaction • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 42185-27-3 ]

Nitriles

A654918 [4594-78-9]

3-(2-Oxocyclohexyl)propanenitrile

Similarity: 1.00

A527862 [62455-70-3]

3-Cyclohexyl-3-oxopropanenitrile

Similarity: 0.95

A538348 [1874-85-7]

3-(2,6-Dioxocyclohexyl)propanenitrile

Similarity: 0.95

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{[proInfo.proName]}

CAS No.: 42185-27-3

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