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39746-01-5

Basic Information
CAS No.: 39746-01-5
Name: (-)-Corey aldehyde benzoate
Article Data: 17
Molecular Structure:
Molecular Structure of 39746-01-5 ((-)-Corey aldehyde benzoate)
Formula: C15H14O5
Molecular Weight: 274.273
Synonyms: 2H-Cyclopenta[b]furan-4-carboxaldehyde,5-(benzoyloxy)hexahydro-2-oxo-, [3aR-(3aa,4a,5b,6aa)]-;(1S,5R,6R,7R)-6-Formyl-7-(benzyloxy)-2-oxabicyclo[3.3.0]octan-3-one;3b-Benzoyloxy-2b-carboxaldehyde-5a-hydroxy-1a-cyclopentaneacetic acid g-lactone;PGX 5;
Density: 1.33 g/cm3
Melting Point: 128-138 °C(lit.)
Boiling Point: 470.427 °C at 760 mmHg
Flash Point: 211.802 °C
PSA: 69.67000
LogP: 1.36250
Synthetic route
39746-00-4

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 1h;100%
With Dess-Martin periodane In dichloromethane at 0 - 10℃; for 2h;96.7%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; carbonic acid dimethyl ester In ethyl acetate at 0 - 5℃; Inert atmosphere;95.6%
39746-00-4

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

A

51260-12-9

(1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde

B

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

Conditions
ConditionsYield
With sulfur trioxide pyridine complex Inert atmosphere;
39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

51260-12-9

(1S,5S)-3-oxo-2-oxabicyclo<3.3.0>oct-6-en-6-carbaldehyde

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78℃; for 1h; Elimination;100%
500871-68-1

dimethyl (7-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

(3aR,4R,5R,6aS)-4-(E)-8-(tert-butyldimethylsilyloxy)-3-oxooct-1-enyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Conditions
ConditionsYield
Stage #1: dimethyl (7-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran; mineral oil at 0 - 20℃; for 2.5h; Inert atmosphere;
100%
39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

1099-45-2

ethyl (triphenylphosphoranylidene)acetate

1027275-03-1

Benzoic acid (3aR,4R,5R,6aS)-4-((E)-2-ethoxycarbonyl-vinyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
In benzene at 20℃; for 0.5h; Wittig reaction;98%
41693-11-2

1-(triphenylphosphoranylidene)-2-hexanone

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

C21H24O5

Conditions
ConditionsYield
In dichloromethane at 20 - 25℃; for 8h; Wittig Olefination;97.1%
36969-89-8

dimethyl 2-oxoheptylphosphonate

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

A

49673-16-7

(3aR,6aS)-4-((E)-3-Oxo-oct-1-enyl)-3,3a,6,6a-tetrahydro-cyclopenta[b]furan-2-one

B

40834-86-4

(3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Horner-Emmons reaction;A 1%
B 96%
61728-15-2

2-oxohexylphosphonic acid dimethyl ester

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

40834-86-4

(3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;96%

(2,2-difluoro-3-phenoxypropyl) diethyl phosphate

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

209861-00-7

(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybutan-1-en-1-yl)-hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate

Conditions
ConditionsYield
Stage #1: (2,2-difluoro-3-phenoxypropyl) diethyl phosphate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 30℃; for 0.25h; Inert atmosphere; Cooling with ice;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran; mineral oil at 40℃; for 2h;
93.6%
36969-89-8

dimethyl 2-oxoheptylphosphonate

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

40834-86-4

(3aR,4R,5R,6aS)-benzoic acid 2-oxo-4-[(1E)-3-oxo-oct-1-enyl]-hexahydro-cyclopenta[b]furan-5-yl ester

Conditions
ConditionsYield
Stage #1: dimethyl 2-oxoheptylphosphonate With lithium hydroxide In tert-butyl methyl ether at 20℃; for 1h;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tert-butyl methyl ether; water at 20℃; for 1h;
91.5%
Stage #1: dimethyl 2-oxoheptylphosphonate; (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one With lithium chloride In tetrahydrofuran; dichloromethane at -20℃; for 2.5h;
Stage #2: With triethylamine In tetrahydrofuran; dichloromethane at -5℃; for 19h;
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Specification

This chemical is called (-)-Corey aldehyde benzoate, and its systematic name is (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate. With the molecular formula of C15H14O5, its molecular weight is 274.27. The CAS registry number of this chemical is 39746-01-5.

Other characteristics of the (-)-Corey aldehyde benzoate can be summarised as followings: (1)ACD/LogP: 1.01; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 4; (6)ACD/BCF (pH 7.4): 4; (7)ACD/KOC (pH 5.5): 100; (8)ACD/KOC (pH 7.4): 100; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 69.67 Å2; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 68.312 cm3; (15)Molar Volume: 206.271 cm3; (16)Polarizability: 27.081×10-24cm3; (17)Surface Tension: 53.183 dyne/cm; (18)Density: 1.33 g/cm3; (19)Flash Point: 211.802 °C; (20)Enthalpy of Vaporization: 73.298 kJ/mol; (21)Boiling Point: 470.427 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
1.SMILES: O=C2O[C@H]3C[C@@H](OC(=O)c1ccccc1)[C@H](C=O)[C@H]3C2
2.InChI: InChI=1/C15H14O5/c16-8-11-10-6-14(17)19-12(10)7-13(11)20-15(18)9-4-2-1-3-5-9/h1-5,8,10-13H,6-7H2/t10-,11-,12+,13-/m1/s1
3.InChIKey: NDHMOBCVFGMXRK-FVCCEPFGBU