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Cyclopentylpropionyl chloride is a synthetic intermediate that plays a crucial role in the development of pharmaceutical compounds. It is characterized by its unique chemical structure, which consists of a cyclopentyl group attached to a propionyl chloride moiety. This structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of new and innovative drugs.

104-97-2

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104-97-2 Usage

Uses

Used in Pharmaceutical Industry:
Cyclopentylpropionyl chloride is used as a synthetic intermediate for the development of a new family of type 3 17β-Hydroxysteroid dehydrogenase inhibitors. These inhibitors are important in the treatment of various medical conditions, as they help regulate the activity of enzymes involved in the synthesis and metabolism of steroid hormones.
Used in Chemical Synthesis:
Cyclopentylpropionyl chloride is also used in the synthesis of 3-cyclopentylpropanamido)methylboronic acid, a compound that has potential applications in various chemical and pharmaceutical processes. The unique structure of cyclopentylpropionyl chloride allows it to react with other molecules, facilitating the formation of new compounds with specific properties and functions.

Check Digit Verification of cas no

The CAS Registry Mumber 104-97-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 104-97:
(5*1)+(4*0)+(3*4)+(2*9)+(1*7)=42
42 % 10 = 2
So 104-97-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H13ClO/c9-8(10)6-5-7-3-1-2-4-7/h7H,1-6H2

104-97-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A17715)  3-Cyclopentylpropionyl chloride, 98%   

  • 104-97-2

  • 25g

  • 572.0CNY

  • Detail
  • Alfa Aesar

  • (A17715)  3-Cyclopentylpropionyl chloride, 98%   

  • 104-97-2

  • 100g

  • 1963.0CNY

  • Detail
  • Aldrich

  • (268593)  Cyclopentanepropionylchloride  98%

  • 104-97-2

  • 268593-10ML

  • 645.84CNY

  • Detail

104-97-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Cyclopentylpropanoyl chloride

1.2 Other means of identification

Product number -
Other names Cyclopentanepropionyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-97-2 SDS

104-97-2Synthetic route

3-cyclopentylpropionic acid
140-77-2

3-cyclopentylpropionic acid

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

Conditions
ConditionsYield
With thionyl chloride In toluene Heating;100%
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 23℃;100%
With pyridine; thionyl chloride for 5h; Reflux;83.85%
oxalyl dichloride
79-37-8

oxalyl dichloride

3-cyclopentylpropionic acid
140-77-2

3-cyclopentylpropionic acid

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

Conditions
ConditionsYield
In dichloromethane
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

N'-(4-bromobenzyl)-N,N-dimethylethane-1,2-diamine
99862-34-7

N'-(4-bromobenzyl)-N,N-dimethylethane-1,2-diamine

N-(4-bromo-benzyl)-3-cyclopentyl-N-(2-dimethylamino-ethyl)-propionamide
864741-96-8

N-(4-bromo-benzyl)-3-cyclopentyl-N-(2-dimethylamino-ethyl)-propionamide

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

(S)-4-Benzyl-2-oxazolidinone
90719-32-7

(S)-4-Benzyl-2-oxazolidinone

(4S)-4-benzyl-3-(3-cyclopentylpropanoyl)-1,3-oxazolidin-2-one

(4S)-4-benzyl-3-(3-cyclopentylpropanoyl)-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane
100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃;
100%
Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: cyclopentanepropanoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
90%
p-cresol
106-44-5

p-cresol

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

p-tolyl 3-cyclopentylpropanoate
1616633-30-7

p-tolyl 3-cyclopentylpropanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
pyrrolidine
123-75-1

pyrrolidine

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-1-(pyrrolidin-1-yl)propan-1-one
544683-75-2

3-cyclopentyl-1-(pyrrolidin-1-yl)propan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;100%
4-methyl-5-phenyloxazolidin-2-one
77943-39-6

4-methyl-5-phenyloxazolidin-2-one

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

(4R,5S)-3-(3-cyclopentylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one
944385-34-6

(4R,5S)-3-(3-cyclopentylpropanoyl)-4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h;99%
5,7-diiodo-8-hydroxyquinoline
83-73-8

5,7-diiodo-8-hydroxyquinoline

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

C17H17I2NO2

C17H17I2NO2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;99%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

C24H21N5O4

C24H21N5O4

C32H33N5O5

C32H33N5O5

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;97%
1-indoline
496-15-1

1-indoline

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-1-(indolin-1-yl)propan-1-one

3-cyclopentyl-1-(indolin-1-yl)propan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;97%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

5-(3-cyclopentylpropionyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
264209-01-0

5-(3-cyclopentylpropionyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3h;96%
With pyridine In dichloromethane at 0 - 20℃; for 12.5h;
7-amino-2,2-dimethylbenzo[1,3]dioxin-4-one
842137-44-4

7-amino-2,2-dimethylbenzo[1,3]dioxin-4-one

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide
866931-69-3

3-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 4h;96%
1,1-Dichloroethylene
75-35-4

1,1-Dichloroethylene

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

C10H15Cl3O
1093748-04-9

C10H15Cl3O

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃;96%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

2-amino-6-ethyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-amino-6-ethyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-ethyl-4,5,6,7-tetrahydro-benzo-[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-ethyl-4,5,6,7-tetrahydro-benzo-[b]thiophene-3-carboxylic acid propyl ester

Conditions
ConditionsYield
In acetone Reflux;92.18%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

benzene
71-43-2

benzene

3-cyclopentyl-1-phenylpropan-1-one
28861-25-8

3-cyclopentyl-1-phenylpropan-1-one

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 18h;92%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

1-Methoxynaphthalene
2216-69-5

1-Methoxynaphthalene

C19H22O2

C19H22O2

Conditions
ConditionsYield
With aluminum (III) chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 5℃; for 2h; Inert atmosphere;91.8%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one
92841-65-1

(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one

(4S,5R)-1-(3-Cyclopentyl-propionyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

(4S,5R)-1-(3-Cyclopentyl-propionyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

Conditions
ConditionsYield
In acetonitrile at 80℃;91%
2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester
302561-09-7

2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

2-(3-cyclopentylpropanamido)-4,5,6,7-tetrahydro-benzo[b]-thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-4,5,6,7-tetrahydro-benzo[b]-thiophene-3-carboxylic acid propyl ester

Conditions
ConditionsYield
In acetone Reflux;90.85%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

2-amino-6-tert-pentyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-amino-6-tert-pentyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-tert-pentyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-tert-pentyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid propyl ester

Conditions
ConditionsYield
In acetone Reflux;90.03%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentylpropanamide
935-10-4

3-cyclopentylpropanamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 1.5h; Inert atmosphere;90%
With ammonia In tetrahydrofuran; water at 0 - 25℃;
With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;592 mg
With ammonium hydroxide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

diphenyl sulfide
139-66-2

diphenyl sulfide

bis-{[4-(3-cyclopentyl-1-one)propyl]phenylene}sulfide

bis-{[4-(3-cyclopentyl-1-one)propyl]phenylene}sulfide

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 10℃; for 3.5h; Cooling with ice;90%
2,6-diethylaniline
579-66-8

2,6-diethylaniline

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-N-(2,6-diethylphenyl)propanamide
551910-86-2

3-cyclopentyl-N-(2,6-diethylphenyl)propanamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃;89%
benzyl 4-{[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-methyl} benzoate
842137-58-0

benzyl 4-{[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-methyl} benzoate

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

benzyl 4-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}benzoate
842137-59-1

benzyl 4-{[(3-cyclopentylpropanoyl)(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]methyl}benzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 4h;89%
8-amino quinoline
578-66-5

8-amino quinoline

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-N-(quinolin-8-yl)propanamide
723257-88-3

3-cyclopentyl-N-(quinolin-8-yl)propanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;89%
With triethylamine In dichloromethane at 0 - 20℃;
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

C10H11N3S2

C10H11N3S2

3-cyclopentyl-N-(5-((2-methylbenzyl)thio)-1,3,4-thiadiazol-2-yl)propanamide

3-cyclopentyl-N-(5-((2-methylbenzyl)thio)-1,3,4-thiadiazol-2-yl)propanamide

Conditions
ConditionsYield
In dichloromethane at 25℃; for 4h;88.6%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

1,4-diamino-9,10-anthraquinone
128-95-0

1,4-diamino-9,10-anthraquinone

1,4-bis(3-cyclopentanepropionamido)-9,10-anthracenedione

1,4-bis(3-cyclopentanepropionamido)-9,10-anthracenedione

Conditions
ConditionsYield
With pyridine In various solvent(s) at 20℃; for 24h;87%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

5-(3-cyclopentyl-1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(3-cyclopentyl-1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃; for 0.25h;
Stage #2: cyclopentanepropanoyl chloride In dichloromethane at 0 - 20℃; for 5h;
87%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

2-amino-6-isopropyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-amino-6-isopropyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-isopropyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid propyl ester

2-(3-cyclopentylpropanamido)-6-isopropyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid propyl ester

Conditions
ConditionsYield
In acetone Reflux;86.07%
2-(7-methyl-4-piperazin-1-yl-quinazolin-2-yl)-phenol
879274-64-3

2-(7-methyl-4-piperazin-1-yl-quinazolin-2-yl)-phenol

cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

3-cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one

3-cyclopentyl-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)propan-1-one

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; dichloromethane at -20 - -10℃; for 0.5h;86%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

3-cyclopentyl-N-(2,6-dimethylphenyl)propanamide
560080-77-5

3-cyclopentyl-N-(2,6-dimethylphenyl)propanamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃;86%
cyclopentanepropanoyl chloride
104-97-2

cyclopentanepropanoyl chloride

diphenyl sulfide
139-66-2

diphenyl sulfide

1-(4-phenylthiophenyl)-(3-cyclopentyl)-prop-1-one
1196481-07-8

1-(4-phenylthiophenyl)-(3-cyclopentyl)-prop-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In 1,1-dichloroethane at 0 - 15℃; for 3.5h; Inert atmosphere;86%

104-97-2Relevant articles and documents

Synthesis and Evaluation of 1,3,4-Thiadiazole Derivatives Containing Cyclopentylpropionamide as Potential Antibacterial Agent

Zhang, Min,Xu, Weiming,Wei, Kun,Liu, Hongwu,Yang, Qin,Liu, Qin,Yang, Liyun,Luo, Yuqin,Xue, Wei

, (2019)

This study aimed to identify new strategies for the control of these plant bacterial diseases by combining a pharmacophoric group of different bioactive compounds. A series of 3-cyclopentylpropionamide containing 1,3,4-thiadiazole derivatives was synthesized and characterized via 1H-NMR, 13C-NMR, and HRMS. Bioassay results indicated that compounds 7a, 7d, 7j, 7m, 7n, and 7s had excellent antibacterial activity compared with the positive control. Among them, compound 7a exhibited remarkable inhibitory effect against Xoo with an EC50 of 21.41?μg/mL, which surpassed that of thiodiazole copper (67.71?μg/mL) and bismerthiazol (69.05?μg/mL). Greenhouse condition tests further revealed that 7a had approximately equal curative activity and better protection activity (41.58%) against bacterial leaf blight of rice than that of thiodiazole copper and bismerthiazol (46.86 and 42.25%, respectively). Structure–activity relationship analysis exhibited that sulfone fragment favored inhibition. Overall, this study suggested that derivatives containing 1,3,4-thiadiazole 3-cyclopentylpropanamide can be used as new lead compounds for bactericide studies.

Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes

Hu, Qu-Ping,Cheng, Jing,Wang, Ying,Shi, Jie,Wang, Bi-Qin,Hu, Ping,Zhao, Ke-Qing,Pan, Fei

, p. 4457 - 4462 (2021)

The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.

Design and Synthesis of 2-Methyl-7-aminobenzoxazole as Auxiliary in the Palladium(II)-Catalyzed Arylation of a beta-Positioned C(sp3)-H Bond

Luo, Feihua,Yang, Jun,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge

, p. 887 - 893 (2016)

A palladium(II)-catalyzed direct arylation of methylene C(sp3)-H bonds by 2-methyl-7-aminobenzoxazole as an effective auxiliary is reported. This process exhibited high beta-site selectivity, broad substrate scope, and compatibility with different functional groups with moderate to high yields up to 89%.

Cationic lipid compound, composition containing same and application

-

Paragraph 0103, (2021/06/22)

The invention provides a cationic lipid compound, a composition containing the cationic lipid compound and application of the cationic lipid compound. In order to provide more choices for delivery of preparations such as nucleic acid drugs, gene vaccines, small molecule drugs and the like, the invention provides a cationic lipid compound shown in the general formula or pharmaceutically available salts thereof. The cationic lipid compound provided by the invention can be used for delivering DNA, RNA or small molecule drugs, enriches the types of cationic lipid compounds, and has important significance for the development and application of nucleic acid preventive and therapeutic agents.

Remote Directed Isocyanation of Unactivated C(sp3)-H Bonds: Forging Seven-Membered Cyclic Ureas Enabled by Copper Catalysis

Zhang, Hongwei,Tian, Peiyuan,Ma, Lishuang,Zhou, Yulu,Jiang, Cuiyu,Lin, Xufeng,Xiao, Xiao

supporting information, p. 997 - 1002 (2020/02/15)

Reported herein is an unprecedented copper-catalyzed site-selective ?-C(sp3)-H bonds activation of aliphatic sulfonamides for constructing the synthetically useful seven-membered N-heterocycles. A key to success is the use of in-situ-formed amide radicals, to activate the inert C(sp3)-H bond, and inexpensive TMSNCO, as a coupling reagent under mild conditions. To the best of our knowledge, this represents the first use of alkylamine derivatives as a five-membered synthon to prepare a seven-membered N-heterocycles.

Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds

Zhang, Hongwei,Zhou, Yulu,Tian, Peiyuan,Jiang, Cuiyu

supporting information, (2019/03/19)

A method for site-selective intermolecular δ/?-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN.

Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters

Sun, Jun,Yoshiiwa, Toshiya,Iwata, Takayuki,Shindo, Mitsuru

supporting information, p. 6585 - 6588 (2019/09/30)

Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.

Non- C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation

Zhou, Zijun,Chen, Shuming,Hong, Yubiao,Winterling, Erik,Tan, Yuqi,Hemming, Marcel,Harms, Klaus,Houk,Meggers, Eric

supporting information, p. 19048 - 19057 (2019/12/04)

A new class of chiral ruthenium catalysts is introduced in which ruthenium is cyclometalated by two 7-methyl-1,7-phenanthrolinium heterocycles, resulting in chelating pyridylidene remote N-heterocyclic carbene ligands (rNHCs). The overall chirality results from a stereogenic metal center featuring either a or Δabsolute configuration. This work features the importance of the relative metal-centered stereochemistry. Only the non-C2-symmetric chiral-at-ruthenium complexes display unprecedented catalytic activity for the intramolecular C(sp3)-H amidation of 1,4,2-dioxazol-5-ones to provide chiral -lactams with up to 99:1 er and catalyst loadings down to 0.005 mol % (up to 11 ?200 TON), while the C2-symmetric diastereomer favors an undesired Curtius-type rearrangement. DFT calculations elucidate the origins of the superior C-H amidation reactivity displayed by the non-C2-symmetric catalysts compared to related C2-symmetric counterparts.

Primary, Secondary, and Tertiary γ-C(sp3)-H Vinylation of Amides via Organic Photoredox-Catalyzed Hydrogen Atom Transfer

Chen, Hui,Guo, Liangliang,Yu, Shouyun

supporting information, p. 6255 - 6259 (2018/10/05)

An efficient strategy for primary, secondary and tertiary aliphatic γ-C(sp3)-H vinylation of amides with alkenylboronic acids is reported. These reactions are catalyzed by visible-light organic photoredox agents. Regioselective γ-C(sp3)-H vinylation of amides is controlled by a 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

Selective α-Oxyamination and Hydroxylation of Aliphatic Amides

Li, Xinwei,Lin, Fengguirong,Huang, Kaimeng,Wei, Jialiang,Li, Xinyao,Wang, Xiaoyang,Geng, Xiaoyu,Jiao, Ning

supporting information, p. 12307 - 12311 (2017/09/11)

Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.

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