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[ CAS No. 62173-99-3 ] {[proInfo.proName]}

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Chemical Structure| 62173-99-3
Chemical Structure| 62173-99-3
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Product Details of [ 62173-99-3 ]

CAS No. :62173-99-3 MDL No. :MFCD00274325
Formula : C15H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :JFKWZVQEMSKSBU-AWEZNQCLSA-N
M.W : 242.27 Pubchem ID :667423
Synonyms :

Safety of [ 62173-99-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 62173-99-3 ]

* 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 [ 62173-99-3 ]

[ 62173-99-3 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 908094-04-2 ]
  • [ 611-71-2 ]
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  • 2
  • [ 62173-99-3 ]
  • phenyl-sulfooxy-acetic acid benzyl ester [ No CAS ]
  • 3
  • [ 611-71-2 ]
  • [ 100-51-6 ]
  • [ 62173-99-3 ]
  • 4
  • [ 67-56-1 ]
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  • 5
  • [ 64-17-5 ]
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  • [ 774-40-3 ]
  • 6
  • [ 14758-41-9 ]
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  • 7
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  • [ 71-36-3 ]
  • [ 14007-02-4 ]
  • 8
  • [ 62173-99-3 ]
  • [ 62977-82-6 ]
YieldReaction ConditionsOperation in experiment
50% With benzeneseleninic acid; In water; acetone; at 40℃; for 6.0h; 1mmol of theMandelic acid methyl ester0.05 mmolBenzene selenite(CAS: 6996-92-5)Mixed in2 mL of acetone,The reaction was stirred at a temperature of 60 C for 6 hours at a mixed system.After the reaction, the solvent was evaporated to dryness, separated by preparative thin layer chromatography,The oxidation product, methyl benzoylformate, was obtained in a yield of 73%.
  • 11
  • [ 100-44-7 ]
  • sodium salt of/the/ mandelic acid [ No CAS ]
  • [ 62173-99-3 ]
  • 12
  • [ 51146-57-7 ]
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  • (R)-2-(4-Isobutyl-phenyl)-propionic acid (S)-carboxy-phenyl-methyl ester [ No CAS ]
  • 13
  • [ 91-01-0 ]
  • [ 611-71-2 ]
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  • 15
  • 3-endo-dicarboxylic acid [ No CAS ]
  • [ 62173-99-3 ]
  • (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-en-2, 3-dicarboxylic acid 2-(benzyl D-mandelate) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; sodium chloride; In tetrahydrofuran; hexane; (1) Preparation of (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-en-2, 3-dicarboxylic acid 2-(benzyl D-mandelate) ester 2 STR17 In a nitrogen atmosphere, a solution 5.33 g (22.0 mmol) of benzyl D-mandelate in 50 ml of tetrahydrofuran (THF) is cooled to -78 C., then 13.13 ml (21.0 mmol) of 1.6M solution of n-butyllithium in hexane is added dropwise and the mixture is stirred for 15 minutes. To the reaction mixture is added a solution of 3.32 g (20.0 mmol) of bicyclo[2.2.1]hept-5-en-2-endo, 3-endo-dicarboxylic acid 1 in 20 ml of THF and the resulting mixture is stirred for an hour at -78 C. The reaction mixture is acidified with 2N hydrochloric acid and the product is extracted with ethyl acetate. The organic layer is washed with water and an aqueous solution of sodium chloride and concentrated to give 9.33 g of the crude product 2 which is purified by column chromatography on silica gel (toluene-ethyl acetate). IR(film)numax: 3600-2400, 1748, 1710, 1498, 1456, 1342, 1257, 1208, 1165, 1084, 1072, 912, 732, 696 cm-1.
  • 16
  • 3-endo-dicarboxylic anhydride [ No CAS ]
  • [ 62173-99-3 ]
  • (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-en-2, 3-dicarboxylic acid 2-(benzyl D-mandelate) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; sodium chloride; In tetrahydrofuran; hexane; (1) Preparation of (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-en-2, 3-dicarboxylic acid 2-(benzyl D-mandelate) ester 2 STR8 In a nitrogen atmosphere, a solution of benzyl D-mandelate (5.33 g (22.0 mmol)) in 50 ml of tetrahydrofuran (THF) is cooled to -78 C., then 13.13 ml (21.0 mmol) of 1.6M solution of n-butyllithium in hexane is added dropwise and the mixture is stirred for 15 minutes. To the reaction mixture is added a solution of 3.32 g (20.0 mmol) of bicyclo [2.2.1]hept-5-en-2-endo, 3-endo-dicarboxylic anhydride 1 in 20 ml of THF and the resulting mixture is stirred for an hour at -78 C. The reaction mixture is acidified with 2N hydrochloric acid and the product is extracted with ethyl acetate. The organic layer is washed with water and an aqueous solution of sodium chloride and concentrated to give 9.33 g of the crude product 2 which is purified by column chromatography on silica gel (toluene - ethyl acetate). IR(film)nu max: 3600-2400, 1748, 1710, 1498, 1456, 1342, 1257, 1208, 1165, 1084, 1072, 912, 732, 696 cm-1.
With n-butyllithium; sodium chloride; In tetrahydrofuran; hexane; EXAMPLE 1 Preparation of (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-en-2,3-dicarboxylic acid, 2-(benzyl D-mandelate) ester II-1-D(e1) STR18 In a nitrogen atmosphere, a solution of benzyl D-mandelate (5.33 g, 22.0 mmol) in 50 ml of THF was cooled to -78 C., then 13.13 ml (21.0 mmol) of 1.6M solution of n-butyllithium in hexane was added dropwise and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of 3.32 g (20.0 mmol) of bicyclo[2.2.1]hept-5-en-2-endo, 3-endo-dicarboxylic anhydride I-1 in 20 ml of THF and the resulting mixture was stirred for an hour at -78 C. The reaction mixture was acidified with 2N hydrochloric acid and the product was extracted with ethyl acetate. The organic layer was washed with water and an aqueous solution of sodium chloride and concentrated to give 9.33 g of the mixture of the aimed product II-1-D(e1) and its by-product II'-1-D(e1). The aimed product II-1-D(e1) was purified by column chromatography on silica gel (toluene - ethyl acetate). IR(film) numax: 3600-2400, 1748, 1710, 1498, 1456, 1342, 1257, 1208, 1165, 1084, 1072, 912, 732, 696 cm-1. 1 H-NMR(CDCl3 TMS) delta ppm: 1.33(ABq, Apart, J=8.9 Hz; 1H), 1.48(ABq, Bpart, J=8.9 Hz, 1H), 3.16(br. s, 1H), 3.21(br. s, 1H), 3.30(dABq, Apart, J=3.2, 10.2 Hz, 1H), 3.47(dABq, Bpart, J=3.4 Hz, 10.2 Hz, 1H), 5.13(s, 2H), 5.97(s, 1H), 6.11(dABq, Apart, J=2.9 Hz, 5.9 Hz, 1H), 6.28(dABq, Bpart, J=2.8, 5.9 Hz, 1H), 7.13~7.52(m, 10H).
  • 17
  • [ 144-55-8 ]
  • [ 611-71-2 ]
  • [ 62173-99-3 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; benzyl alcohol; In chloroform; benzene; EXAMPLE 5 Preparation of cephalotaxyl L-mandelate, trichloroethylcarbonate ester STR9 L-Mandelic acid (10 g.), 6.91 g. of benzyl alcohol, and 75 mg. of p-toluenesulfonic acid in 70 ml. of benzene was refluxed under a Dean-Stark trap for a total of 28 hours on 4 consecutive days. The crude benzyl ester was obtained by successively concentrating the liquor and cooling it to about 10 C. a number of times. The fractions melting between 97 C. and 105 C. were combined, dissolved in CHCl3 and washed twice with 15-ml. portions of 5% aqueous NaHCO3 solution. After evaporation of the CHCl3, the product was recrystallized from benzene to give benzyl L-mandelate, m.p. 104-106 C., yield 42%.
  • 18
  • [ 611-71-2 ]
  • [ 62173-99-3 ]
YieldReaction ConditionsOperation in experiment
91% With toluene-4-sulfonic acid; benzyl alcohol; In benzene; (1) Benzyl D-mandelate STR53 A solution of 85.1 g (559 mmol) of D-mandelic acid, 65 ml (628 mmol) of benzyl alcohol, and 1.01 g (5.35 mmol) of p-toluenesulfonic acid in 700 ml of benzene was refluxed for 6.5 hours. The mixture was washed with water and concentrated. The residue was recrystallized from ether to give 123.5 g of the aimed compound D-2 in 91% yield. Mp. 103.5-105 C. Anal. Calcd. (%) for C15 H14 O3: C, 74.36; H, 5.82; Found (%): C, 74.53; H, 5.90. 1 H-NMR(CDCl3 -TMS) delta ppm: 3.44(d, J=5.6 Hz, 1H), 5.14(ABq, Apart, J=12.3 Hz, 1H), 5.22(d, J=5.6 Hz, 1H), 5.24(ABq, Bpart, J=12.3 Hz, 1H), 7.15~7.50(m, 10H). [alpha]D =-55.7+-1.0 (CHCl3, C=1.003%, 24 C.).
  • 19
  • [ 524-38-9 ]
  • [ 62173-99-3 ]
  • [ 931119-44-7 ]
YieldReaction ConditionsOperation in experiment
98% With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at -20℃; for 1.0h; To a solution of benzyl-2-hydroxy-2-phenylacetate (2.42 g, 10 mmol), N-hydroxyphthalimide (1.96 g, 12 mmol) and PPh3 (3.4 g, 13 mmol) in CH2Cl2 (30 mL) was added DIAD (2.63 g, 13 mmol) at -20 C. The resulting mixture was stirred at -20 C. for 1 hour. The reaction mixture was concentrated and purified by flash chromatography (silica gel, Hexanes/CH2Cl2=1/3) giving 3.8 g (98%) of the title compound.
  • 20
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  • [ 73818-55-0 ]
  • [ 165337-03-1 ]
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  • [ 102-16-9 ]
  • 22
  • [ 1192-63-8 ]
  • [ 62173-99-3 ]
  • [ 1041400-01-4 ]
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