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Chemical Structure| 91-48-5 Chemical Structure| 91-48-5

Structure of 91-48-5

Chemical Structure| 91-48-5

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Product Details of [ 91-48-5 ]

CAS No. :91-48-5
Formula : C15H12O2
M.W : 224.25
SMILES Code : O=C(O)/C(C1=CC=CC=C1)=C/C2=CC=CC=C2
MDL No. :MFCD00004252
InChI Key :BIDDLDNGQCUOJQ-SDNWHVSQSA-N
Pubchem ID :700620

Safety of [ 91-48-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 91-48-5 ]

* 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.

  • Upstream synthesis route of [ 91-48-5 ]

[ 91-48-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 91-48-5 ]
  • [ 3333-15-1 ]
  • [ 17040-62-9 ]
YieldReaction ConditionsOperation in experiment
83 % ee With 5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin In 1,4-dioxane; water at 22.84℃; General procedure: A 5percentPd/C catalyst was obtained from N.E. Chemcat (5percent STD type)in a 51percent wet form, and stored at 280 K until use. PCA (1) wasused after recrystallization from acetone, and all the other substrates(2–9) were prepared by Perkin reaction using a methodreported [15]. The hydrogenation conditions were as follows.5percentPd/C (23 mg calculated as a dry form, 10 mol of Pd) was pretreatedat 353 K in wet dioxane (dioxane containing v/v 2.5percent water)under atmospheric hydrogen for 30 min. After cooling to 296 K,CD (0.05–100 mol) in wet dioxane was added to the catalyst.A substrate (0.5 mmol) and then benzylamine (1.0 equiv.) in wetdioxane were added (total amount of the solvent = 10 ml) to the CDmodifiedcatalyst with stirring. Within 3–6 h the substrate was fullyconverted to the expected products at 296 K under 105 Pa of hydrogen.The product eepercent were determined by chiral high performanceliquid chromatography (HPLC). The relative initial hydrogenationrates were determined at 25percent conversion by measuring hydrogenconsumption and normalized to the corresponding rates at 0-M ofCD (relative initial rate = observed initial rate over the modified catalyst/the initial rate over the unmodified catalyst). HPLC conditionsare shown in Table 1.
82 % ee
Stage #1: With 5%-palladium/activated carbon; hydrogen; benzylamine; Cinchonidin In 1,4-dioxane; water at 22.84 - 79.84℃; for 2 h;
Stage #2: With hydrogenchloride In water
General procedure: All chemicals were purchasedfrom commercial sources andpurified viadistillation when necessary. 6-hydroxy CD (6-OHCDin Scheme 1) was preparedfrom QN via de-methylation(55percentyield). The enantioselective hydrogenation reactions ofPCA and DMPCA were carried out over chiral modified Pd/Casfollows.4,9Astirring suspension of 5percentPd/C (43 mg as a50percentcontent, wetform, STD-type supplied by N.E. Chemcat)and 5 mL of 2.5percentH2O-containing dioxane was heated under105Pa ofhydrogen at 353 Kfor 30 min. After cooling to 296 K,asolution of modifier (0.001512 mg)in the solvent (1 mL)was added. After 30 min, 0.5 mmol of the substrate acidinthe solvent (4 mL) and then benzylamine (BnNH2,55L) wasadded. The Pd/substrate molar ratio was 10/500 (inmolin10mL of polar wet dioxane). The reaction temperature and pressure were 296 K and 105Pa of hydrogen, respectively. Thecatalytic activity was calculated from the rate of hydrogenconsumption at 25percentconversion. The hydrogen consumptioncontinuedfor 13h. After additional 2h, a 2M HCl aqueoussolution (1 mL) was added to the solution,followed byfiltration ofthe reaction mixture to remove the catalyst. Thefiltratewas extracted with ethyl acetate (2 mL) and washed with water(2 mL). The extract was analyzed by HPLC with a chiral column (Daicel OJ-3for PCA and AD-3for DMPCA).
54 % ee
Stage #1: With 5%-palladium/activated carbon; hydrogen; benzylamine; (+)-cinchonine In 1,4-dioxane; water at 22.84℃;
General procedure: All chemicals were purchasedfrom commercial sources andpurified viadistillation when necessary. 6-hydroxy CD (6-OHCDin Scheme 1) was preparedfrom QN via de-methylation(55percentyield). The enantioselective hydrogenation reactions ofPCA and DMPCA were carried out over chiral modified Pd/Casfollows.4,9Astirring suspension of 5percentPd/C (43 mg as a50percentcontent, wetform, STD-type supplied by N.E. Chemcat)and 5 mL of 2.5percentH2O-containing dioxane was heated under105Pa ofhydrogen at 353 Kfor 30 min. After cooling to 296 K,asolution of modifier (0.001512 mg)in the solvent (1 mL)was added. After 30 min, 0.5 mmol of the substrate acidinthe solvent (4 mL) and then benzylamine (BnNH2,55L) wasadded. The Pd/substrate molar ratio was 10/500 (inmolin10mL of polar wet dioxane). The reaction temperature and pressure were 296 K and 105Pa of hydrogen, respectively. Thecatalytic activity was calculated from the rate of hydrogenconsumption at 25percentconversion. The hydrogen consumptioncontinuedfor 13h. After additional 2h, a 2M HCl aqueoussolution (1 mL) was added to the solution,followed byfiltration ofthe reaction mixture to remove the catalyst. Thefiltratewas extracted with ethyl acetate (2 mL) and washed with water(2 mL). The extract was analyzed by HPLC with a chiral column (Daicel OJ-3for PCA and AD-3for DMPCA).
References: [1] Chemistry Letters, 1996, # 10, p. 897 - 898.
[2] Chemistry Letters, 1998, # 2, p. 161 - 162.
[3] Chemistry Letters, 1998, # 2, p. 161 - 162.
[4] Journal of Organic Chemistry, 1996, vol. 61, # 16, p. 5510 - 5516.
[5] Chemistry Letters, 1999, # 7, p. 635 - 636.
[6] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 11, p. 2635 - 2641.
[7] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 10, p. 1971 - 1972.
[8] Helvetica Chimica Acta, 2003, vol. 86, # 5, p. 1753 - 1759.
[9] Tetrahedron Asymmetry, 2005, vol. 16, # 9, p. 1573 - 1575.
[10] Angewandte Chemie - International Edition, 2005, vol. 44, # 27, p. 4209 - 4212.
[11] Journal of Catalysis, 2009, vol. 262, # 1, p. 57 - 64.
[12] Advanced Synthesis and Catalysis, 2008, vol. 350, # 17, p. 2804 - 2814.
[13] Journal of Catalysis, 2010, vol. 276, # 2, p. 259 - 267.
[14] Journal of Catalysis, 2010, vol. 276, # 2, p. 259 - 267.
[15] Catalysis Letters, 2012, vol. 142, # 3, p. 345 - 351.
[16] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178.
[17] Chemistry--A European Journal, 2012, vol. 18, # 39, p. 12458 - 12478,21.
[18] Chemistry--A European Journal, 2012, vol. 18, # 39, p. 12458 - 12478,21.
[19] Organometallics, 2013, vol. 32, # 4, p. 1075 - 1084.
[20] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 223 - 233.
[21] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 223 - 233.
[22] Catalysis Today, 2015, vol. 245, p. 129 - 133.
[23] Applied Catalysis A: General, 2015, vol. 505, p. 319 - 325.
[24] Journal of Raman Spectroscopy, 2015, vol. 46, # 11, p. 1102 - 1109.
[25] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 10, p. 1187 - 1191.
[26] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 10, p. 1187 - 1191.
  • 2
  • [ 91-48-5 ]
  • [ 3333-15-1 ]
References: [1] Tetrahedron, 1969, vol. 25, p. 2301 - 2311.
[2] Arkivoc, 2012, vol. 2012, # 5, p. 16 - 27.
  • 3
  • [ 13702-35-7 ]
  • [ 91-48-5 ]
  • [ 3333-15-1 ]
  • [ 17040-62-9 ]
References: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 223 - 233.
  • 4
  • [ 36854-27-0 ]
  • [ 91-48-5 ]
  • [ 3333-15-1 ]
  • [ 17040-62-9 ]
References: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 223 - 233.
 

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