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3731-38-2

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3731-38-2 Usage

Uses

3-Quinuclidinone is used in preparation of Maropitant.

Check Digit Verification of cas no

The CAS Registry Mumber 3731-38-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,7,3 and 1 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 3731-38:
(6*3)+(5*7)+(4*3)+(3*1)+(2*3)+(1*8)=82
82 % 10 = 2
So 3731-38-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2

3731-38-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Azabicyclo[2.2.2]octan-3-one

1.2 Other means of identification

Product number -
Other names 1-azabicyclo[2.2.2]octan-3-one

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:3731-38-2 SDS

3731-38-2Synthetic route

3-quinuclidinone hydrochloride
1193-65-3

3-quinuclidinone hydrochloride

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With sodium carbonate; sodium hydroxide In water at 0℃; for 0.5h;100%
With sodium hydrogencarbonate In water at 20℃; for 0.166667h;88%
With ammonia In methanol
3-quinuclidinol
1619-34-7

3-quinuclidinol

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With potassium tert-butylate; C29H30ClNOP2Ru(1+) In acetone at 60℃; for 10h; Product distribution / selectivity; Inert atmosphere;95%
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium sulfite In water; acetonitrile at 60℃; under 760.051 Torr; for 15h;95%
With dmap; [2,2]bipyridinyl; 2-azatricyclo[3.3.1.13,7]dec-2-yloxidanyl; copper(l) chloride In acetonitrile at 20℃; for 2h; chemoselective reaction;94%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; 9-azanoradamantane N-oxyl; acetic acid In dichloromethane at 20℃; for 8h;87%
With 1-methyl-2-azaadamantane-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 30h;46%
3-<(N-benzyl)acetamido>quinuclidine
161153-87-3

3-<(N-benzyl)acetamido>quinuclidine

A

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

B

1,4-ethano-1,2,3,4-tetrahydrobenzo-1,5-naphthyridine

1,4-ethano-1,2,3,4-tetrahydrobenzo-1,5-naphthyridine

C

5-acetyl-1,4-ethano-1,2,3,4,5,6-hexahydrobenzo-1,5-naphthyridine

5-acetyl-1,4-ethano-1,2,3,4,5,6-hexahydrobenzo-1,5-naphthyridine

Conditions
ConditionsYield
With palladium diacetate In acetic acid; acetonitrile for 80h; Heating;A 5 % Chromat.
B 20 % Chromat.
C 37%
(S)-3-quinuclidinol
34583-34-1

(S)-3-quinuclidinol

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With octahydro-2,5-epiminopentalen-7-yloxidanyl; acetic acid; sodium nitrite at 20℃; for 4h; air;34%
ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate
1838-39-7

ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With potassium; toluene anschliessend mit konz. Salzsaeure;
With potassium ethoxide; toluene anschliessend mit konz. Salzsaeure;
Quinuclidine
100-76-5

Quinuclidine

A

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

B

quinuclidin-2-one
74384-65-9

quinuclidin-2-one

Conditions
ConditionsYield
With pyridine; acetic acid; zinc; Fe3O(OAc)6Pyr35 Yield given. Yields of byproduct given;
quinuclidin-3-yl butyrate butyric acid salt

quinuclidin-3-yl butyrate butyric acid salt

A

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

B

(R)-quinuclidin-3-yl butyrate
65732-89-0

(R)-quinuclidin-3-yl butyrate

Conditions
ConditionsYield
Stage #1: quinuclidin-3-yl butyrate butyric acid salt With calcium hydroxide; Aspergillus melleus protease In water at 25℃; for 24h;
Stage #2: With Raney Co In o-xylene at 142℃; for 10h;
4-carbethoxypiperidine
1126-09-6

4-carbethoxypiperidine

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3
2: potassium; toluene / anschliessend mit konz. Salzsaeure
View Scheme
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Raney nickel; dioxane / 175 - 180 °C / 91938.4 Torr / Hydrogenation
2: K2CO3
3: potassium; toluene / anschliessend mit konz. Salzsaeure
View Scheme
1-azabicyclo[2.2.2]octan-3-ol

1-azabicyclo[2.2.2]octan-3-ol

A

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

B

C7H10ClNO

C7H10ClNO

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; chlorine; sodium carbonate In dichloromethane at 25℃; Mechanism; Reagent/catalyst; Time;A 88 %Chromat.
B 9.2 %Chromat.
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

3-Cyano-1-azabicyclo[2.2.2]octane
51627-76-0

3-Cyano-1-azabicyclo[2.2.2]octane

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane; ethanol at 0 - 40℃; for 2.5h;100%
With potassium tert-butylate In 1,2-dimethoxyethane; ethanol at -5 - 20℃; for 3.83333h;88%
With ethanol; potassium tert-butylate In 1,2-dimethoxyethane 1.) 5-10 deg C, 0.5 h, 2.) 40 deg C, 2.5 h;74%
With potassium tert-butylate In 1,2-dimethoxyethane at 0 - 5℃; for 20h; Substitution;
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

trimethyl phosphonoacetate
5927-18-4

trimethyl phosphonoacetate

2-(1-azabicyclo[2.2.2]oct-3-ylidene)acetic acid methyl ester
94764-01-9

2-(1-azabicyclo[2.2.2]oct-3-ylidene)acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Wittig Olefination; Inert atmosphere;
Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; Wittig Olefination; Inert atmosphere;
100%
Stage #1: trimethyl phosphonoacetate With sodium In methanol at 0℃; for 1h;
Stage #2: 3-Quinuclidinone In methanol at 0℃; for 0.5h; Horner-Wadsworth-Emmons reaction;
Stage #3: In methanol at 50℃; for 18h;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: 3-Quinuclidinone In tetrahydrofuran at 0 - 20℃; Wadsworth-Emmons reaction;
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h;
Stage #2: 3-Quinuclidinone In tetrahydrofuran; mineral oil at 20℃; for 18h;
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

(R)-quinuclidin-3-ol
25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
With potassium tert-butylate; hydrogen; RuCl2[(S,S)-xylskewphos] (dmf)n In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;100%
With trans-RuCl2((S)-BINAP)((R)-iphan); potassium tert-butylate; hydrogen In isopropyl alcohol at 25℃; under 38002.6 Torr; for 24h; optical yield given as %ee; enantioselective reaction;99%
With potassium tert-butylate; hydrogen; RuBr2[(S,S)-xylskewphos](6-Me-pica) In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;95%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

(3-chloroizoxasol-5-yl)methyloxyamine hydrochloride

(3-chloroizoxasol-5-yl)methyloxyamine hydrochloride

1-azabicyclo[2.2.2]octan-3-one O-(3-chloroiszoxazol-5-ylmethyl)oxime

1-azabicyclo[2.2.2]octan-3-one O-(3-chloroiszoxazol-5-ylmethyl)oxime

Conditions
ConditionsYield
With pyridine; 4 A molecular sieve In ethanol at 23℃; for 24h;98%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

5-chloro-pyridin-2-yl hydrazine
27032-63-9

5-chloro-pyridin-2-yl hydrazine

quinuclidin-3-one (5-chloropyridin-2-yl)hydrazone

quinuclidin-3-one (5-chloropyridin-2-yl)hydrazone

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;98%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Conditions
ConditionsYield
With RuCl[(S)-daipena][(S)-3,5-xylyl-BINAP]; potassium tert-butylate; hydrogen In isopropyl alcohol at 10℃; under 22801.5 Torr; for 6h; optical yield given as %ee; enantioselective reaction;97%
With potassium tert-butylate; hydrogen; RuCl2[(R,R)-xylskewphos][(S)-ampy] In ethanol; tert-butyl alcohol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;95%
With potassium tert-butylate; hydrogen; RuCl2[(R,R)-xylskewphos][(S)-ampy] In ethanol at 0 - 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity;89%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

N'-[1-Aza-bicyclo[2.2.2]oct-(3Z)-ylidene]-hydrazinecarboxylic acid tert-butyl ester
136681-83-9

N'-[1-Aza-bicyclo[2.2.2]oct-(3Z)-ylidene]-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
In Petroleum ether for 24h; Heating;96%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

2-(quinuclidin-3-ylidene)acetonitrile
51526-85-3

2-(quinuclidin-3-ylidene)acetonitrile

Conditions
ConditionsYield
With potassium hydroxide In water96%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran for 0.333333h; Inert atmosphere;
Stage #2: 3-Quinuclidinone In tetrahydrofuran for 20h;
95%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

quinoline-4-carboxaldehyde
4363-93-3

quinoline-4-carboxaldehyde

2-(quinolin-4-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one
23443-71-2

2-(quinolin-4-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran at 20℃; for 2h;95%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

1’-azaspiro[oxirane-2,3’-bicyclo[2.2.2]octane]
41353-91-7

1’-azaspiro[oxirane-2,3’-bicyclo[2.2.2]octane]

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 15℃; Reflux;95%
In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dimethyl sulfoxide77%
Stage #1: trimethylsulfoxonium iodide With sodium hydride In N,N-dimethyl-formamide for 5h;
Stage #2: 3-Quinuclidinone In N,N-dimethyl-formamide for 4.5h; Johnson-Corey-Chaykovsky Reaction;
70%
In water; dimethyl sulfoxide
In water; dimethyl sulfoxide
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

aniline
62-53-3

aniline

N-phenylquinuclidin-3-amine
6238-20-6

N-phenylquinuclidin-3-amine

Conditions
ConditionsYield
Stage #1: 3-Quinuclidinone; aniline In ethanol Reflux;
Stage #2: With sodium tetrahydroborate In ethanol
95%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

3-quinuclidinol
1619-34-7

3-quinuclidinol

Conditions
ConditionsYield
With sodium methylate92.8%
With sodium hydroxide; zinc diacetate at 20 - 25℃; for 45h; electrochemical reduction; lead cathode;80%
With copper(II) choride dihydrate; lithium In tetrahydrofuran; mineral oil at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;65%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

malononitrile
109-77-3

malononitrile

3-(dicyanomethylene)quinuclidine

3-(dicyanomethylene)quinuclidine

Conditions
ConditionsYield
In chloroform for 2h; Ambient temperature;92%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

benzaldehyde
100-52-7

benzaldehyde

(Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one
24123-89-5

(Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one

Conditions
ConditionsYield
With sodium hydroxide for 1.5h; Heating / reflux;91.2%
With sodium hydroxide In ethanol for 1.5h; Reflux;91.2%
With sodium hydroxide In ethanol for 16h; Reflux; Inert atmosphere;87%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

Cinnamyl bromide
4392-24-9

Cinnamyl bromide

1-cinnamyl-1-azoniabicyclo<2.2.2>octan-3-one bromide
79841-02-4

1-cinnamyl-1-azoniabicyclo<2.2.2>octan-3-one bromide

Conditions
ConditionsYield
In acetonitrile91%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

1-(3-aminopropyl)-3-butylimidazolium tetrafluoroborate

1-(3-aminopropyl)-3-butylimidazolium tetrafluoroborate

C17H31N4(1+)*BF4(1-)

C17H31N4(1+)*BF4(1-)

Conditions
ConditionsYield
Stage #1: 3-Quinuclidinone; 1-(3-aminopropyl)-3-butylimidazolium tetrafluoroborate In methanol at 20℃;
Stage #2: With sodium tetrahydroborate In methanol at 0℃;
91%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

1-bromo-3-phenylprop-2-yne
1794-48-5

1-bromo-3-phenylprop-2-yne

1-(3-phenylprop-2-ynyl)-1-azoniabicyclo<2.2.2>octan-3-one bromide
79841-53-5

1-(3-phenylprop-2-ynyl)-1-azoniabicyclo<2.2.2>octan-3-one bromide

Conditions
ConditionsYield
In acetonitrile90%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

quinoline-4-carboxaldehyde
4363-93-3

quinoline-4-carboxaldehyde

(S)-2-(Hydroxy-quinolin-4-yl-methyl)-1-aza-bicyclo[2.2.2]octan-3-one
571166-64-8

(S)-2-(Hydroxy-quinolin-4-yl-methyl)-1-aza-bicyclo[2.2.2]octan-3-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 30℃; for 336000h;90%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

ethyl iodide
75-03-6

ethyl iodide

1-ethylquinuclidinium iodide
3618-93-7

1-ethylquinuclidinium iodide

Conditions
ConditionsYield
With potassium carbonate In methanol90%
3,5-dimethyl-1,2-oxazole
300-87-8

3,5-dimethyl-1,2-oxazole

3-Quinuclidinone
3731-38-2

3-Quinuclidinone

3-Hydroxy-3-(3-methyl-5-isoxazolyl) methyl-1-azabicyclo[2.2.2]octane

3-Hydroxy-3-(3-methyl-5-isoxazolyl) methyl-1-azabicyclo[2.2.2]octane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane90%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

2-(4-Benzyloxyphenylmethylene)-3-oxoquinuclidine
111896-93-6

2-(4-Benzyloxyphenylmethylene)-3-oxoquinuclidine

Conditions
ConditionsYield
With sodium hydroxide In ethanol 1.) reflux, 2.5 h, 2.) 20 deg, 16 h;89%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

2-(3,4,5-trimethoxybenzoylamino)-3-ethoxycarbonylthieno<2,3-b>quinuclidine
112290-20-7

2-(3,4,5-trimethoxybenzoylamino)-3-ethoxycarbonylthieno<2,3-b>quinuclidine

Conditions
ConditionsYield
With triethylamine In benzene for 6h; Heating;89%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

trisylhydrazine
39085-59-1

trisylhydrazine

C22H35N3O2S
154182-94-2

C22H35N3O2S

Conditions
ConditionsYield
In diethyl ether at 20℃; for 15h;89%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

tosylmethylisocyanide

tosylmethylisocyanide

3-Cyano-1-azabicyclo[2.2.2]octane
51627-76-0

3-Cyano-1-azabicyclo[2.2.2]octane

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane; ethanol at -5 - 20℃; for 3.83333h;88%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

formaldehyd
50-00-0

formaldehyd

2-methylenequinuclidin-3-one
5291-26-9

2-methylenequinuclidin-3-one

Conditions
ConditionsYield
With dimethyl amine In ethanol at 70℃;86%
With dimethyl amine In ethanol; water at 70℃; for 19h; Reflux;43%
With dimethyl amine In ethanol; water for 19h; Reflux;43%
3-Quinuclidinone
3731-38-2

3-Quinuclidinone

1-(3-aminopropyl)-3-butylimidazol-1-ium bromide

1-(3-aminopropyl)-3-butylimidazol-1-ium bromide

1-[3-(1-aza-bicyclo[2.2.2]oct-3-ylamino)-propyl]-3-butyl-3H-imidazol-1-ium; bromide

1-[3-(1-aza-bicyclo[2.2.2]oct-3-ylamino)-propyl]-3-butyl-3H-imidazol-1-ium; bromide

Conditions
ConditionsYield
Stage #1: 3-Quinuclidinone; 1-(3-aminopropyl)-3-butylimidazol-1-ium bromide In methanol at 20℃; for 12h;
Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 4h;
86%

3731-38-2Relevant articles and documents

New and potent quinuclidine-based antimicrobial agents

Kastelic, Andreja Radman,Od?ak, Renata,Pezdirc, Iskra,Sovi?, Karlo,Hrenar, Tomica,Ga?parovi?, Ana ?ipak,Sko?ibu?i?, Mirjana,Primo?i?, Ines

, (2019)

Developing new antibiotics is currently very important since antibiotic resistance is one of the biggest problems of global health today. In the search for a new class of potential antimicrobial agents, ten new compounds were designed and synthesized based on the quinuclidinium heterocyclic core and the oxime functional group. The antimicrobial activity was assessed against a panel of representative gram-positive and gram-negative bacteria. All compounds demonstrated potent activity against the tested microorganisms, with the minimum inhibitory concentration (MIC) values ranging from 0.25 to 256.00 μg/mL. Among the tested compounds, two quaternary compounds, para-N-chlorobenzyl and meta-N-bromobenzyl quinuclidinium oximes, displayed the most potent and broad-spectrum activity against both gram-positive and gram-negative bacterial strains (MIC values from 0.25 to 4.00 μg/mL), with the lowest value for the important multidrug resistant gram-negative pathogen Pseudomonas aeruginosa. In the case of Klebsiella pneumoniae, activity of those compounds are 256-fold and 16-fold better than gentamicin, respectively. MTT assays showed that compounds are nontoxic for human cell lines. Multi-way analysis was used to separately reduce dimensionality of quantum chemical data and biological activity data to obtain a regression model and the required parameters for the enhancement of biological activity.

Directional Intermolecular Interactions for Precise Molecular Design of a High- Tc Multiaxial Molecular Ferroelectric

Yang, Chen-Kai,Chen, Wang-Nan,Ding, Yan-Ting,Wang, Jing,Rao, Yin,Liao, Wei-Qiang,Xie, Yongfa,Zou, Wennan,Xiong, Ren-Gen

, p. 1781 - 1787 (2019/01/26)

Quasi-spherical molecules have recently been developed as promising building blocks for constructing high-performance molecular ferroelectrics. However, although the modification of spherical molecules into quasi-spherical ones can efficiently lower the crystal symmetry, it is still a challenge to precisely arouse a low-symmetric polar crystal structure. Here, by introducing directional hydrogen-bonding interactions in the molecular modification, we successfully reduced the cubic centrosymmetric Pm3m space group of [quinuclidinium]ClO4 at room temperature to the orthorhombic polar Pna21 space group of [3-oxoquinuclidinium]ClO4. Different from the substituent groups of -OH, -CH3, and -CH2, the addition of a -O group with H-acceptor to [quinuclidinium]+ forms directionally N-H?O-C hydrogen-bonded chains, which plays a critical role in the generation of polar structure in [3-oxoquinuclidinium]ClO4. Systematic characterization indicates that [3-oxoquinuclidinium]ClO4 is an excellent molecular ferroelectric with a high Curie temperature of 457 K, a large saturate polarization of 6.7 μC/cm2, and a multiaxial feature of 6 equiv ferroelectric axes. This work demonstrates that the strategy of combining quasi-spherical molecule building blocks with directional intermolecular interactions provides an efficient route to precisely design new eminent molecular ferroelectrics.

Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes

Budweg, Svenja,Junge, Kathrin,Beller, Matthias

supporting information, p. 14143 - 14146 (2019/12/02)

Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.

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