CAS No.130931-83-8,(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	130931-83-8
Name:	(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
Article Data:	23

Formula:	C₆H₇NO
Molecular Weight:	109.128
Synonyms:	2-Azabicyclo[2.2.1]hept-5-en-3-one,(1S)-;(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one;
EINECS:	421-830-3
Density:	1.199 g/cm³
Melting Point:	94-97 °C(lit.)
Boiling Point:	319.302 °C at 760 mmHg
Flash Point:	167.131 °C
Appearance:	off-white to beige crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
PSA:	29.10000
LogP:	0.38970

Synthetic route

: 157810-20-3
(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With ammonium hydroxide In methanol at 20℃; for 4h;	95%
With ammonium hydroxide In methanol for 12h; Ambient temperature;	45%
With methanol; ammonium hydroxide for 13h; Ambient temperature;	38%

: 49805-30-3
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With resin-supported recombinant Candida antarctica lipase B; water In tert-butyl methyl ether at 60℃; for 102h; enantioselective reaction;	48%
With citrophilla (ATCC No.21285) In phosphate buffer for 24h; pH=7.5;	31.8%
With lipase B Candida antarctica recombined fromAspergillus oryzae In aq. phosphate buffer for 168h; Reagent/catalyst; Enzymatic reaction;	n/a
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction 3: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction 3: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme

: 49805-30-3
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

A: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

B: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With lipase B from Candida antarctica In water; isopropyl alcohol at 60℃; for 4h; Enzymatic reaction; stereospecific reaction;	A 46% B 48%
With water In tert-butyl methyl ether Enzymatic reaction; optical yield given as %ee;

: 169104-33-0
(1S,4R)-2-[(4-methoxyphenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 2.5h;	26%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1R,6S)-6-Chlorocarbonyl-cyclohex-3-enecarboxylic acid isopropyl ester

A: 88586-06-5
(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With sodium tetrahydroborate; camphor-10-sulfonic acid 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h; Yield given. Multistep reaction;

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

A: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With brucine In methanol at 20℃; for 6h;
With Methylobacterium sp. Y1-6 at 30℃; for 24h; Overall yield = 19 %Chromat.;	A n/a B n/a
With malonamidase E2 (MAE2) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	A n/a B n/a
With Cu-(R)-2,2'-dihydroxy-1,1'-binaphthalene-6,6'-dicarboxylic acid organic framework silica composite In ethanol; hexane Resolution of racemate;

: 157732-10-0
2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 45 percent / aq. NH3 / methanol / 12 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 2: 38 percent / Nh4OH, MeOH / 13 h / Ambient temperature View Scheme

: 181136-52-7
(1S,6R)-6-(isopropoxycarbonyl)cyclohex-3-enecarboxylic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 3 h / Ambient temperature 2: 1.) NaBH4; 2.) camphorsulfonic acid / 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h View Scheme

: 935-79-5
cis-1,2,3,6-tetrahydrophthalic anhydride

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) TADDOL / 1.) Et2O, r.t., 3 h; 2.) THF, -20 degC, 10 d 2: CH2Cl2 / 3 h / Ambient temperature 3: 1.) NaBH4; 2.) camphorsulfonic acid / 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h View Scheme

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Specification

The (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one, with the CAS registry number 130931-83-8, is also known as ZINC00158452. It belongs to the product categories of Chiral Building Blocks; Lactams; Organic Building Blocks. This chemical's molecular formula is C₆H₇NO and molecular weight is 109.12588. Its IUPAC name is called (1R,4S)-3-azabicyclo[2.2.1]hept-5-en-2-one. This chemical is off-white to beige crystalline powder. The product should be sealed and stored in cool and dry place.

Physical properties of (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one: (1)ACD/LogP: -1.22; (2)ACD/LogD (pH 5.5): -1.22; (3)ACD/LogD (pH 7.4): -1.22; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.18; (7)ACD/KOC (pH 7.4): 5.18; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.545; (11)Molar Refractivity: 28.8 cm³; (12)Molar Volume: 91 cm³; (13)Surface Tension: 39.4 dyne/cm; (14)Density: 1.198 g/cm³; (15)Flash Point: 167.1 °C; (16)Enthalpy of Vaporization: 56.09 kJ/mol; (17)Boiling Point: 319.3 °C at 760 mmHg; (18)Vapour Pressure: 0.000342 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C2C=CC1NC2=O
(2)Isomeric SMILES: C1[C@@H]2C=C[C@H]1NC2=O
(3)InChI: InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
(4)InChIKey: DDUFYKNOXPZZIW-CRCLSJGQSA-N