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Chemistry
Organic Building Blocks
Aryls
phenoxypropanoic
(R)-2-Phenoxypropanoic acid
Chemistry
Organic Building Blocks
Aryls
Ethers Carboxylic Acids Benzene Compounds
phenoxypropanoic
benzyl 2-phenoxypropanoic acid

[ CAS No. 1129-46-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Product Details of [ 1129-46-0 ]

CAS No. :1129-46-0 MDL No. :MFCD04038077
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SXERGJJQSKIUIC-SSDOTTSWSA-N
M.W : 166.17 Pubchem ID :643326
Synonyms :

Safety of [ 1129-46-0 ]

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

Application In Synthesis of [ 1129-46-0 ]

* 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 [ 1129-46-0 ]

[ 1129-46-0 ] Synthesis Path-Downstream   1~75

  • 1
  • [ 1129-46-0 ]
  • [ 32403-66-0 ]
Reference： [1]Arkiv foer Kemi,1953,vol. 6,p. 365,370
  • 2
  • [ 551-16-6 ]
  • [ 1129-46-0 ]
  • [ 34378-72-8 ]
Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 3934 - 3938
  • 3
  • [ 1004-84-8 ]
  • [ 1129-46-0 ]
  • (1R,6S,7S)-7-<<((R)-1-phenoxyethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane [ No CAS ]
  • (1S,6R,7R)-7-<<((R)-1-phenoxyethyl)carbonyl>oxy>-9-methylenebicyclo<4.3.0>nonane [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6579 - 6587
[2]Journal of Organic Chemistry,1992,vol. 57,p. 6579 - 6587
  • 4
  • [ 940-31-8 ]
  • [ 1129-46-0 ]
  • [ 87860-35-3 ]
Reference： [1]Agricultural and Biological Chemistry,1984,vol. 48,p. 1373 - 1374
  • 5
  • [ 42412-84-0 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Tetrahedron Asymmetry,1991,vol. 2,p. 39 - 42
  • 6
  • [ 2065-24-9 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Tetrahedron Asymmetry,1991,vol. 2,p. 39 - 42
[2]Tetrahedron Asymmetry,1991,vol. 2,p. 39 - 42
[3]Canadian Journal of Chemistry,1988,vol. 66,p. 1219 - 1222
[4]Recueil des Travaux Chimiques des Pays-Bas,1992,vol. 111,p. 490 - 495
  • 7
  • [ 2065-24-9 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
  • [ 115880-50-7 ]
  • [ 115880-48-3 ]
Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 4661 - 4664
[2]Tetrahedron Letters,1987,vol. 28,p. 4661 - 4664
  • 8
  • [ 1129-46-0 ]
  • [ 147851-69-2 ]
YieldReaction ConditionsOperation in experiment
99% With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 6h; Oxalyl chloride (1.09 mL, 12.5 mmol) was added to a solution of acid (R)-5 (0.83 g, 5 mmol) and DMF (5 μL) in CH2Cl2 (20 mL). The reaction mixture was stirred at room temperature for 6 h, and then evaporated to dryness under reduced pressure. The residue was dried over P2O5 in vacuo to afford 0.92 g (99%) of compound (R)-2a as a yellowish oil, which had an unpleasant odor. Anal. Calcd for C9H9ClO2: C, 58.55; H, 4.91. Found: C, 58.78; H, 5.07. 1H NMR spectrum was identical to that published for racemic chloride 2a. 5
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
[2]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 9
  • [ 76671-56-2 ]
  • [ 1129-46-0 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide; In ethanol; at 4 - 20℃; for 24h; At first, 2 M NaOH (5.2 mL, 10.4 mmol) was added dropwise to a solution of compound (R)-4 (1.01 g, 5.2 mmol) in ethanol (20 mL) with stirring at 4 C. The reaction mixture was stirred at room temperature for 24 h, and then evaporated to dryness under reduced pressure. The residue was dissolved in water (40 mL), washed with ethyl ether (2 * 10 mL), acidified with 4 M HCl to pH 1-2 and extracted with ethyl ether (4 * 20 mL). The organic layers were washed with saturated aqueous NaCl (2 * 40 mL), dried over MgSO4, and evaporated to dryness under reduced pressure. The residue was recrystallized from hexane to yield 0.77 g (89%) of compound (R)-5 as a colorless solid, mp 86-88 C (hexane) (lit. 85-87 C, 12 83 C 13 ); [α]D20 = +16.2 (c 0.6, CHCl3) {lit. 13 [α]D20 = +19 (c 1.0, CHCl3)}. HPLC (Chiralpak AD, n-hexane-iPrOH-TFA 20:1:0.02): 95.6% ee. Anal. Calcd for C9H10O3: C, 65.05; H, 6.06. Found: C, 64.95; H, 6.24. 1H and 13C NMR spectra were identical to those published for (S)-5.14
Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12616 - 12617
[2]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
[3]Journal of Organic Chemistry,1992,vol. 57,p. 6579 - 6587
[4]Il Farmaco,1993,vol. 48,p. 1401 - 1416
  • 10
  • [ 54656-96-1 ]
  • [ 446878-78-0 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
  • [ 94559-16-7 ]
  • [ 94559-15-6 ]
Reference： [1]Chemische Berichte,1984,vol. 117,p. 3457 - 3462
[2]Chemische Berichte,1984,vol. 117,p. 3457 - 3462
[3]Chemische Berichte,1984,vol. 117,p. 3457 - 3462
  • 11
  • [ 115880-50-7 ]
  • [ 1129-46-0 ]
Reference： [1]Synthetic Communications,2009,vol. 39,p. 3459 - 3470
[2]Il Farmaco,1993,vol. 48,p. 1401 - 1416
  • 12
  • [ 1129-46-0 ]
  • [ 89209-34-7 ]
  • [ 91712-57-1 ]
  • [ 89255-52-7 ]
Reference： [1]Journal of the American Chemical Society,1984,vol. 106,p. 5997
  • 13
  • [ 163104-06-1 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
  • [ 163104-05-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 14
  • (R)-2-Phenoxy-propionic acid (1S,2S,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl ester [ No CAS ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
  • [ 163104-05-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 15
  • (R)-2-Phenoxy-propionic acid (1S,2S,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl ester [ No CAS ]
  • [ 1129-46-0 ]
  • [ 163104-05-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 16
  • [ 940-31-8 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 301 - 302
[2]Russian Chemical Bulletin,2021,vol. 70,p. 900 - 907
    Izv. Akad. Nauk, Ser. Khim.,2021,p. 900 - 907
[3]Chirality,2022
  • 17
  • [ 513-49-5 ]
  • [ 1129-46-0 ]
  • (R)-N-((S)-sec-Butyl)-2-phenoxy-propionamide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 18
  • [ 13250-12-9 ]
  • [ 1129-46-0 ]
  • (R)-N-((R)-sec-Butyl)-2-phenoxy-propionamide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 19
  • D-Valine methyl ester [ No CAS ]
  • [ 1129-46-0 ]
  • (R)-3-Methyl-2-((R)-2-phenoxy-propionylamino)-butyric acid methyl ester [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 20
  • [ 4070-48-8 ]
  • [ 1129-46-0 ]
  • (S)-3-Methyl-2-((R)-2-phenoxy-propionylamino)-butyric acid methyl ester [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 21
  • [ 2627-86-3 ]
  • [ 1129-46-0 ]
  • [ 184178-55-0 ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 22
  • [ 3886-69-9 ]
  • [ 1129-46-0 ]
  • (R)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 7285 - 7290
  • 23
  • [ 184178-55-0 ]
  • [ 1129-46-0 ]
Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 2307 - 2310
  • 24
  • [ 1129-46-0 ]
  • [ 94050-90-5 ]
Reference： [1]Pesticide Science,1996,vol. 46,p. 33 - 35
  • 26
  • inactive form [ No CAS ]
  • [ 1129-46-0 ]
Reference： [1]Bulletin de la Societe Chimique de France,1922,vol. &lt;4&gt; 31,p. 990
    Bulletin de la Societe Chimique de France,1923,vol. &lt;4&gt; 33,p. 459
  • 27
  • [ 1129-46-0 ]
  • /PBMZE017-1320/ [ No CAS ]
  • (S)-2-Phenoxy-propionic acid 3,8,13-triethoxy-7,12-bis-((R)-2-phenoxy-propionyloxy)-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-yl ester [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 1299
  • 28
  • n-butyl 2-phenoxypropionate [ No CAS ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 3698 - 3702
[2]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 1386 - 1390
[3]Bulletin of the Chemical Society of Japan,2008,vol. 81,p. 617 - 622
  • 29
  • [ 908094-01-9 ]
  • [ 1129-46-0 ]
  • [ 115880-50-7 ]
Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7234 - 7242
[2]Organic letters,2002,vol. 4,p. 371 - 373
  • 30
  • [ 940-31-8 ]
  • [ 1129-46-0 ]
Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 7234 - 7242
[2]Organic letters,2002,vol. 4,p. 371 - 373
[3]Tetrahedron Letters,1999,vol. 40,p. 2307 - 2310
  • 31
  • [ 1129-46-0 ]
  • [ 474809-21-7 ]
  • [2-(2-phenoxy-propionylamino)-pyridin-4-ylmethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
Reference： [1]Organic Letters,2002,vol. 4,p. 3423 - 3426
  • 32
  • [ 1129-46-0 ]
  • [ 106-50-3 ]
  • <i>N</i>-(4-amino-phenyl)-2-phenoxy-propionamide [ No CAS ]
Reference： [1]Organic Letters,2002,vol. 4,p. 3423 - 3426
  • 33
  • [ 940-31-8 ]
  • [ 71-36-3 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
  • (R)-2-Phenoxy-propionic acid butyl ester [ No CAS ]
  • (S)-2-Phenoxy-propionic acid butyl ester [ No CAS ]
Reference： [1]Bulletin of the Chemical Society of Japan,2003,vol. 76,p. 399 - 403
  • 34
  • [ 57057-80-4 ]
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Acta Crystallographica Section B: Structural Science,2003,vol. 59,p. 132 - 140
  • 35
  • [ 1129-46-0 ]
  • [ 917-54-4 ]
  • [ 189300-43-4 ]
Reference： [1]Tetrahedron,2004,vol. 60,p. 449 - 457
  • 36
  • [ 32644-15-8 ]
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Organic Letters,2002,vol. 4,p. 3423 - 3426
  • 37
  • [ 10009-70-8 ]
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Organic Letters,2002,vol. 4,p. 3423 - 3426
  • 38
  • 3-(2-phenoxy-propionyl)-4-phenyl-oxazolidin-2-one [ No CAS ]
  • [ 1129-46-0 ]
Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 476 - 482
  • 39
  • N,N-diisopropyl-3-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-3-phenylpropanamine [ No CAS ]
  • [ 1129-46-0 ]
  • (R)-2-[3-(diisopropylamino)-1-phenylpropyl]-4-(2-hydroxyethyl)phenol (R)-2-phenoxypropionic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% In ethyl acetate; at 80℃; for 48h; (S)-2-Phenoxypropionic acid (3.4Og, 20.5 mmol, 1 equiv) was added to a solution of 2-[3- (diisopropylamino)-l-phenylpropyl]-4-(2-hydroxyethyl)phenol (Example 9, 7.28g, 20.5 mmol, 1 equiv) in ethyl acetate. The mixture was heated at 80 0C for 2 days, upon which the mixture was cooled to room temperature, filtered and washed with ethyl acetate and dried in vacuo at 50 0C overnight to give the title compound as a white solid (3.9g, 7.48 mmol, 37% yield, 94% ee).
Reference： [1]Patent: WO2007/138440,2007,A1 .Location in patent: Page/Page column 19-20
  • 40
  • [ 1129-46-0 ]
  • [ 664374-43-0 ]
Reference： [1]Tetrahedron,2004,vol. 60,p. 449 - 457
  • 41
  • [ 1129-46-0 ]
  • <i>N</i>-(4-aminomethyl-pyridin-2-yl)-2-phenoxy-propionamide [ No CAS ]
Reference： [1]Organic Letters,2002,vol. 4,p. 3423 - 3426
  • 42
  • 2-Phenoxy-propionic acid 2,2,2-trifluoro-ethyl ester [ No CAS ]
  • [ 1129-46-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
[2]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
[3]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 43
  • [ 161969-67-1 ]
  • [ 1129-46-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 44
  • [ 161969-69-3 ]
  • [ 1129-46-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
[2]Journal of the Chemical Society. Perkin transactions I,1994,p. 1509 - 1516
  • 45
  • [ 100-67-4 ]
  • copper powder [ No CAS ]
  • [ 1129-46-0 ]
Reference： [1]Il Farmaco,1993,vol. 48,p. 1401 - 1416
[2]Il Farmaco,1993,vol. 48,p. 1401 - 1416
  • 46
  • [ 1129-46-0 ]
  • (1S,2R,5S)-menthyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 47
  • [ 1129-46-0 ]
  • (1R,2S,5R)-menthyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
[2]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 48
  • [ 1129-46-0 ]
  • (S)-1-phenylethyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 49
  • [ 1129-46-0 ]
  • (R)-1-phenylethyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 50
  • [ 1129-46-0 ]
  • (S)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
[2]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 51
  • [ 1129-46-0 ]
  • (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (R)-2-phenoxypropionate [ No CAS ]
Reference： [1]Acta Chemica Scandinavica,1993,vol. 47,p. 492 - 499
  • 52
  • [ 1129-46-0 ]
  • [ 4169-04-4 ]
Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 1299
[2]Journal of the American Chemical Society,1985,vol. 107,p. 1299
  • 53
  • [ 108-95-2 ]
  • phosphorous oxychloride [ No CAS ]
  • [ 1129-46-0 ]
Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 6579 - 6587
  • 54
  • [ 62784-66-1 ]
  • [ 446878-78-0 ]
  • [ 1213744-22-9 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304
  • 55
  • [ 16929-35-4 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1172 - 1179
  • 56
  • [ 940-31-8 ]
  • [ 62784-66-1 ]
  • [ 1213744-22-9 ]
  • [ 1345458-52-7 ]
  • [ 1129-46-0 ]
  • [ 1912-23-8 ]
Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 11296 - 11304
[2]Heterocycles,2012,vol. 86,p. 1227 - 1252
  • 57
  • [ 116435-79-1 ]
  • [ 1129-46-0 ]
Reference： [1]Organic Letters,2012,vol. 14,p. 194 - 197
  • 58
  • [ 1129-46-0 ]
  • 3-(3-tolyl)-1H-1,2,4-triazol-5-amine [ No CAS ]
  • [ 1391916-84-9 ]
Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 715 - 720
  • 59
  • [ 1402665-69-3 ]
  • [ 1129-46-0 ]
  • [ 1419334-50-1 ]
Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8051 - 8054
  • 60
  • [ 1402665-70-6 ]
  • [ 1129-46-0 ]
  • [ 1419334-63-6 ]
Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8051 - 8054
  • 61
  • [ 2065-24-9 ]
  • [ 1129-46-0 ]
  • [ 115880-48-3 ]
Reference： [1]Bioorganic Chemistry,2016,vol. 65,p. 1 - 8
  • 62
  • [ 82419-33-8 ]
  • [ 147851-69-2 ]
  • 7,8-difluoro-3,4-dihydro-3-methyl-N-(2′-phenoxypropionyl)-2H-[1,4]benzoxazine [ No CAS ]
  • [ 1129-46-0 ]
YieldReaction ConditionsOperation in experiment
76% A solution of amine (RS)-1b (0.28g, 0.15mmol) and PhNEt2 (0.22g, 1.5mmol) in toluene (20mL) was added to a solution of acyl chloride 2a (1.84g, 10mmol) [obtained from scalemic acid (R)-3, 96.5% ee] in toluene (30mL). The reaction mixture was kept at room temperature for 24h and then evaporated to dryness under reduced pressure. Acetonitrile (20mL) and saturated aqueous Na2CO3 (20mL) were added to the residue and the reaction mixture was stirred vigorously for 1h, after which acetonitrile was removed under reduced pressure, and the aqueous solution was washed with chloroform (4×15mL), acidified with 4M HCl to pH 1-2 and extracted with chloroform (4×10mL). The organic layers were washed with saturated aqueous NaCl (4×20mL), dried over MgSO4 and evaporated to dryness under reduced pressure to afford 1.26g (76%) of acid (R)-5 as a colorless solid, mp 88-90C; [α]D20=+21.1 (c 1.0, CHCl3). HPLC (Chiralpak AD, n-hexane-iPrOH-TFA 20:1:0.02): 99.6% ee. Anal. Calcd for C9H10O3: C, 65.05; H, 6.06. Found: C, 65.18; H, 6.25.
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 63
  • (3S,2'R)-3,4-dihydro-3-methyl-N-(2'-phenoxypropionyl)-2H-[1,4]benzothiazine [ No CAS ]
  • [ 1185454-10-7 ]
  • [ 1129-46-0 ]
YieldReaction ConditionsOperation in experiment
92%; 94% With hydrogenchloride; In water; acetic acid; at 90 - 95℃; for 20h; A solution of acyl chloride (R)-2a (0.92g, 5mmol) in toluene (50mL) was added to a solution of amine 1c (1.65g, 10mmol) in toluene (50mL) under stirring at -20C. The reaction mixture was stirred at -20C for 24h, then successively washed with 4M HCl (2×50mL), saturated aqueous NaCl (3×100mL), 5% NaHCO3 (2×50mL) and H2O (2×100mL), dried over MgSO4, and evaporated to dryness under reduced pressure. The residue was recrystallized from n-hexane-ethyl acetate to afford 1.25g (80%) of amide (S,R)-6c (de >99.9% according to GC) as colorless crystals. Amide (S,R)-6c (1.25g, 4mmol) was dissolved in glacial acetic acid (9mL), after which concentrated HCl (9mL) was added to the resulting solution. The reaction mixture was heated at 90-95C for 20h, then cooled to room temperature, evaporated to half the volume, poured into 4M HCl (50mL) and extracted with ethyl acetate (3×10mL). The organic layers were washed with saturated aqueous NaCl (3×20mL), dried over MgSO4, and evaporated to dryness. The residue was purified by flash column chromatography on silica gel (n-hexane-ethyl acetate) to yield 0.62g (94%) of acid (R)-5 as colorless crystals, mp 84-86C, [α]D20=+21.1 (c 1.0, CHCl3). HPLC (Chiralpak AD, n-hexane-iPrOH-TFA 20:1:0.02): 99.4% ee. Anal. Calcd for C9H10O3: C, 65.05; H, 6.06. Found: C, 65.03; H, 6.21. 1H and 13C NMR spectra were identical to those published for (S)-5.14 The acidic aqueous layer was alkalized with Na2CO3 and extracted with benzene (3×10mL). The organic layers were washed with water (3×20mL), dried over Na2SO4, and evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (from n-hexane-benzene to benzene) to afford 0.61g (92%) of amine (S)-1c as a colorless oil. [α]D20=-77.8 (c 1.0, CHCl3) {lit.15 [α]D20=-79.0 (c 1.2, CHCl3)}. HPLC (Chiralcel OD-H, n-hexane-iPrOH-MeOH 100:1:0.5): >99.9% ee. 1H and 13C NMR spectra were identical to those published for (S)-1c.15 HRMS (ESI) calcd for C9H12NS [M+H]+ 166.0685. Found: 166.0687.
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 64
  • [ 1129-46-0 ]
  • (3S,2'R)-7,8-difluoro-3,4-dihydro-3-methyl-N-(2'-phenoxypropionyl)-2H-[1,4]benzoxazine [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 65
  • [ 1129-46-0 ]
  • (2R,2'R)-2-methyl-N-(2'-phenoxypropionyl)indoline [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 66
  • [ 1129-46-0 ]
  • (2R,2'R)-6-fluoro-2-methyl-N-(2'-phenoxypropionyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 67
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 1231 - 1237
  • 68
  • [ 1129-46-0 ]
  • [ 109-07-9 ]
  • (R)-2-methylpiperazine tri((R)-2-phenoxypropionic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
48 g In isopropyl alcohol;Reflux; (Comparative Example 2) (±) -2- methylpiperazine 15.0g (0.15mol), (R) -2- phenoxypropionicacid 69.8 g (0.42 mol), was mixed 2-propanol 250 ml, heated to reflux the contents, lysis did.After dissolution, the solution was cooled overnight to 25 C. The resulting separated crystalswere dried to give crude diastereomeric salt 48.0 g. [Alpha] D: + 21.2 (C = 1.0, methanol). (In FIG. 2, 2 crystallization, 3 crystallization was described as) The crude diastereomeric salt of 2-propanol from twice recrystallized by, purified diastereomeric salt (R)-2-methylpiperazine three ((R) -2-phenoxypropionic acid) 41.3g. [Alpha] D: + 23.0 (C = 1.0, methanol) melting point 149 C.
Reference： [1]Patent: JP2016/37495,2016,A .Location in patent: Paragraph 0062; 0063
  • 69
  • ethyl 6,6-dimethyl-3-[1-(trimethylsilyl)cyclopropanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate [ No CAS ]
  • [ 1129-46-0 ]
  • (R)-N-[6,6-dimethyl-5-(2-phenoxypropanoyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl]-1-(trimethylsilyl)cyclopropane carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% To a solution of 154 mg (0.424 mmol) of ethyl 6,6-dimethyl-3-[1-(trimethylsilyl)cyclopropanecarboxamido]-5,6-dihydr opyrrolo[3,4-c]pyrazole-2(4H)-carboxylate synthesized in the similar manner as in Reference Example 46 and 0.38 ml (2.2 mmol) of DIPEA in 2 ml of dehydrated dichloromethane, a solution of the obtained concentration residue in 1 ml of dehydrated dichloromethane was added at 0C in a nitrogen atmosphere and then stirred for 1.5 hours with the temperature unchanged. Subsequently, 0.24 ml (2.2 mmol) of N,N-dimethylethane-1,2-diamine was added to the reaction solution at 0C and then stirred at room temperature for 2 hours. After the completion of the reaction, the reaction solution diluted with dichloromethane was washed with a 5% aqueous potassium bisulfate solution and then separated into an aqueous layer and an organic layer. The aqueous layer was subjected to extraction with dichloromethane twice, and then, all of the obtained organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to silica gel column chromatography (DIOL silica gel, elution solvent: n-hexane:ethyl acetate = 80:20 to 50:50 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 155 mg of the title compound (yield: 83%) as a white solid. Mass spectrum (CI, m/z): 441 [M+1]+. 1H-NMR spectrum (400 MHz, DMSO-d6) δ: 12.33 & 12.02 (br s, total 1H), 10.03 - 9.76 (m, 1H), 7.30 - 7.22 (m, 2H), 6.94 - 6.87 (m, 1H), 6.85 - 6.78 (m, 2H), 4.95 - 4.70 (m, 2H), 4.67 - 4.51 (m, 1H), 1.70 - 1.52 (m, 6H), 1.45 (d, J = 6.4 Hz, 3H), 0.98 (br s, 2H), 0.80 - 0.59 (m, 2H), 0.01 (br s, 9H).
Reference： [1]Patent: EP3214086,2017,A1 .Location in patent: Paragraph 0413-0417
  • 70
  • ethyl 6,6-dimethyl-3-[1-(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate [ No CAS ]
  • [ 1129-46-0 ]
  • (R)-N-[6,6-dimethyl-5-(2-phenoxypropanoyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl]-1-(trimethylsilyl)cyclobutane carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% To a solution of 58.3 mg (0.351 mmol) of <strong>[1129-46-0](R)-2-phenoxypropanoic acid</strong> in 2 ml of dehydrated DMF, 0.12 ml (0.69 mmol) of DIPEA and 152 mg (0.354 mmol) of (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholin ocarbenium hexafluorophosphate [COMU (trade name)] were added in this order at 0C in a nitrogen atmosphere and then stirred for 20 minutes with the temperature unchanged. Subsequently, 104 mg (0.274 mmol) of ethyl 6,6-dimethyl-3-[1-(trimethylsilyl)cyclobutanecarboxamido]-5,6-dihydro pyrrolo[3,4-c]pyrazole-1(4H)-carboxylate synthesized in the similar manner as in Reference Example 5 was added at 0C and then stirred at room temperature for 15.5 hours. Subsequently, 0.10 ml (1.7 mmol) of 2-aminoethanol was added to the reaction solution at room temperature and then stirred for 2.5 hours with the temperature unchanged. After the completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added to the reaction solution and stirred, followed by extraction with dichloromethane three times. All of the obtained organic layers were dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The operation of adding toluene to the obtained concentration residue, followed by concentration under reduced pressure again was repeated twice, then the resultant was subjected to silica gel column chromatography (DIOL silica gel, elution solvent: n-hexane:ethyl acetate = 75:25 to 50:50 (V/V)), and a fraction containing the compound of interest was concentrated under reduced pressure. The obtained concentration residue was dissolved in ethyl acetate, then n-hexane was added, and the deposited solid was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain 75 mg of the title compound (yield: 60%) as a white solid. Mass spectrum (EI, m/z): 454 [M]+. 1H-NMR spectrum (400 MHz, DMSO-d6) δ: 12.53 - 11.80 (m, 1H), 9.69 (br s, 1H), 7.30 - 7.21 (m, 2H), 6.94 - 6.87 (m, 1H), 6.85 - 6.78 (m, 2H), 4.90 (q, J = 6.5 Hz, 1H), 4.87 - 4.78 (m, 1H), 4.67 - 4.57 (m, 1H), 2.56 - 2.38 (m, 2H), 2.25 - 2.12 (m, 2H), 1.87 - 1.74 (m, 2H), 1.67 - 1.58 (m, 6H), 1.46 (d, J = 6.5 Hz, 3H), 0.06 (s, 9H).
Reference： [1]Patent: EP3214086,2017,A1 .Location in patent: Paragraph 0404-0406
  • 71
  • [ 74533-11-2 ]
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
YieldReaction ConditionsOperation in experiment
42.61% 28.23 g of phenol (0.3 mol) was added to a 1000 mL three-necked flask.50mL 300g / L sodium hydroxide aqueous solution, stirring at room temperature under an anaerobic condition at 500rpm for 1h,0.36 mol of sodium (S)-2-chloropropionate prepared in the step (1) was slowly added dropwise using a constant pressure separatory funnel.Add 0.075 mol of potassium iodide and reflux at 125 C for 1.5 h. During the reflux,The pH of the reaction system is 12-13. After the reaction, the reaction solution is acidified with hydrochloric acid to pH=4.0, and a yellow oil precipitates.The aqueous phase is separated from the hot water, and the aqueous phase is acidified to pH ≤ 2.0 with hydrochloric acid to precipitate a large amount of white powdery solid, which is filtered and dried.(R)-PPA 23.52 g, molar yield 42.61%.
Reference： [1]Patent: CN109111355,2019,A .Location in patent: Paragraph 0020; 0036; 0046; 0049; 0050
  • 72
  • rimantadine [ No CAS ]
  • [ 1129-46-0 ]
  • C9H10O3*C12H21N [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.9% In water; acetone; at 20 - 50℃; for 24.5h; General procedure: To the solution of racemic rimantadine 10 in acetone with 5% H2O, resolving reagent 1326 wasadded in acetone with 5% H2O at 50 C. The amount of solvent was adjusted to 12 volumes. Themixture was stirred for 30 min at 50 C, then cooled to room temperature and stirred for 24 h to form thecorresponding salt. The salt was filtered, washed with acetone with 5% H2O, and dried under vacuum(<0.5 mmHg) at room temperature (rt). The solvent for crystallization is indicated in Tables 1-4 foreach particular experiment and salt compound (Supplementary Materials).3.3.1. Rimantadine (10) (R)-2-Phenoxy Propionic Acid (13) 0.5 Eq. Salt (99.7% ee)Molecular weight (Mw): 51.1 g, 92.9% yield, 99.7% ee (S) from 55.0 g, 98.7% ee (S) salt, meltingpoint (mp): 167-171 C. 1H NMR (400 MHz, CD3OD): δ = 7.15-7.29 (m, 2H), 6.80-6.92 (m, 3H), 4.40 (q,J = 6.7 Hz, 1H), 2.75 (q, J = 6.6 Hz, 1H), 1.96-2.09 (m, 3H), 1.55-1.86 (m, 12H), 1.42-1.52 (m, 4H), 1.15 (d,J = 6.6 Hz, 3H).
Reference： [1]Molecules,2019,vol. 24
  • 73
  • rimantadine [ No CAS ]
  • [ 1129-46-0 ]
  • C9H10O3*C12H21N [ No CAS ]
  • C9H10O3*C12H21N [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetone; at 0 - 50℃; for 19.5h; To the solution of rac-Rimantadine 10 (100 g, 558 mmol) in acetone with 5% H2O (600 mL) wasadded (R)-2- phenoxypropionic acid 13 (46.3 g, 279 mmol) in acetone with 5% H2O (600 mL). Themixture was stirred for 30 minutes at 50 C, then cooled to room temperature and stirred for 15 hoursto form precipitate. After that the suspension was cooled to 0 C and stirred for 4 hours. Theprecipitate was filtered, washed with acetone with 5% H2O and dried under vacuum at 40 C toafford 1st salt 32 (66.9 g, 34.7%, 88.4% ee).
Reference： [1]Molecules,2019,vol. 24
  • 74
  • [ 29617-66-1 ]
  • [ 108-95-2 ]
  • [ 1129-46-0 ]
YieldReaction ConditionsOperation in experiment
96.6% Add 94.1 g (1 mol) of phenol and170 mL (1.49 mol NaOH) of a 35% mass concentration sodium hydroxide aqueous solution into a 1L four-necked flask. The temperature is raised to 55C and stirred for 30 minutes. Add dropwise (S)-(-)-2-chloropropionic acid 108.5g (1mol), keep it at 60C for 2h condensation reaction, and detect the area normalized content of raw material phenol in liquid phase Use concentrated hydrochloric acid (mass concentration of36%) to adjust the pH of the obtained product material to 1, and then filter and dry the obtained material to obtain an off-white solid, namely R-(+)-2-phenoxypropionic acid 160.6 g, liquid content HPLC=98.6%, yield 96.6%;
95% With water; sodium hydroxide; at 50 - 70℃;Inert atmosphere; To 1000ml, add 94g (1mol, 1.0eq) of phenol, 108.5g (1mol, 1.0eq) of S-2-chloropropionic acid, 200g (1.5mol, 1.5eq) of 30% sodium hydroxide, 470g of water, and replace with nitrogen three times. It is heated to 50-70 C, and the reaction is kept for 4 to 6 hours. The reaction is completed by HPLC monitoring S-2-chloropropionic acid ≤0.5%.Cool down, adjust pH
Reference： [1]Patent: CN112812002,2021,A .Location in patent: Paragraph 0052-0053; 0055-0056; 0058-0059; 0061-0062
[2]Patent: CN110803987,2020,A .Location in patent: Paragraph 0067-0069
  • 75
  • [ 1129-46-0 ]
  • [ 46232-97-7 ]
YieldReaction ConditionsOperation in experiment
95.1% With N-Bromosuccinimide; In water; N,N-dimethyl-formamide; at 20 - 30℃; for 8h; Dissolve 2-phenoxypropionic acid 838 (0.51 ^ 1, 1.069) in water, add 0.6g (0.0075mol,0 · 015eq), NBS 102g (0.575mol, 1.15eq) was added at 20-30C. After the addition was completed, the reaction was performed at 20-30C for 8h.HPLC monitors that 2-phenoxypropionic acid is less than or equal to 2%. Cool down, adjust pH <1 with 31% hydrochloric acid, separate layers, and cool the water phase toBelow 10C, stir for 30 minutes to crystallize, suction filter to obtain 116.5g of 2- (4-bromophenoxy) propionic acid, yield 95.1%, purity98.7%.
Reference： [1]Patent: CN110803987,2020,A .Location in patent: Paragraph 0070-0072

Tags: 1129-46-0 synthesis path| 1129-46-0 SDS| 1129-46-0 COA| 1129-46-0 purity| 1129-46-0 application| 1129-46-0 NMR| 1129-46-0 COA| 1129-46-0 structure

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benzyl
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phenoxypropanoic
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Aryls

Technical Information

• Acetal Formation • Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hunsdiecker-Borodin Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nomenclature of Ethers • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Preparation of Ethers • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Ethers • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Ring Opening of Oxacyclopropane • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Sulfonation of Benzene • Synthesis of Alcohols from Tertiary Ethers • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • The Nucleophilic Opening of Oxacyclopropanes • Ugi Reaction • Vilsmeier-Haack Reaction
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; ;