Home Cart 0 Sign in  

[ CAS No. 22818-40-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 22818-40-2
Chemical Structure| 22818-40-2
Structure of 22818-40-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 22818-40-2 ]

Related Doc. of [ 22818-40-2 ]

Alternatived Products of [ 22818-40-2 ]

Product Details of [ 22818-40-2 ]

CAS No. :22818-40-2 MDL No. :MFCD00004262
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LJCWONGJFPCTTL-SSDOTTSWSA-N
M.W : 167.16 Pubchem ID :89853
Synonyms :
4-Hydroxy-D-phenylglycine;D-(-)-4-Hydroxyphenylglycine

Calculated chemistry of [ 22818-40-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.72
TPSA : 83.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.57
Log Po/w (XLOGP3) : -2.06
Log Po/w (WLOGP) : 0.15
Log Po/w (MLOGP) : -2.01
Log Po/w (SILICOS-IT) : 0.04
Consensus Log Po/w : -0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.18
Solubility : 255.0 mg/ml ; 1.53 mol/l
Class : Highly soluble
Log S (Ali) : 0.83
Solubility : 1140.0 mg/ml ; 6.79 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.88
Solubility : 22.1 mg/ml ; 0.132 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 22818-40-2 ]

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 [ 22818-40-2 ]

* 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 [ 22818-40-2 ]
  • Downstream synthetic route of [ 22818-40-2 ]

[ 22818-40-2 ] Synthesis Path-Upstream   1~35

  • 1
  • [ 6324-01-2 ]
  • [ 22818-40-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 4, p. 965 - 970
[2] Synthetic Communications, 1994, vol. 24, # 17, p. 2449 - 2459
[3] Tetrahedron Asymmetry, 2000, vol. 11, # 6, p. 1343 - 1351
[4] Journal of the Chemical Society. Perkin transactions 1, 1976, # 5, p. 475 - 481
[5] Patent: CN105418443, 2016, A, . Location in patent: Paragraph 0022; 0023; 0024
  • 2
  • [ 37763-23-8 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
[2] Patent: US2015/112057, 2015, A1, . Location in patent: Paragraph 0062
  • 3
  • [ 67-56-1 ]
  • [ 1327278-14-7 ]
  • [ 22818-40-2 ]
  • [ 37763-23-8 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 4
  • [ 6324-01-2 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Patent: US6639103, 2003, B1, . Location in patent: Page/Page column 12-13
[2] Chirality, 2017, vol. 29, # 6, p. 315 - 324
[3] Chinese Journal of Chemistry, 2017, vol. 35, # 7, p. 1037 - 1042
  • 5
  • [ 54582-01-3 ]
  • [ 22818-40-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1729 - 1735
  • 6
  • [ 2420-17-9 ]
  • [ 22818-40-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 355 - 362
[2] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 715 - 720
[3] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 715 - 720
[4] Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 355 - 362
  • 7
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Tetrahedron Asymmetry, 2004, vol. 15, # 12, p. 1933 - 1936
  • 8
  • [ 1327278-02-3 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 9
  • [ 1327278-09-0 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 10
  • [ 1327278-14-7 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 11
  • [ 1327277-97-3 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 12
  • [ 65448-20-6 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 13
  • [ 38177-33-2 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 14
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
  • [ 37763-23-8 ]
  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 15
  • [ 69598-75-0 ]
  • [ 22818-40-2 ]
  • [ 25698-18-4 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 37, p. 4987 - 4990
  • 16
  • [ 68780-35-8 ]
  • [ 22818-40-2 ]
Reference: [1] Tetrahedron Asymmetry, 1995, vol. 6, # 6, p. 1257 - 1260
  • 17
  • [ 60114-00-3 ]
  • [ 22818-40-2 ]
Reference: [1] Journal of Antibiotics, 1976, vol. 29, # 9, p. 890 - 901
  • 18
  • [ 39391-39-4 ]
  • [ 22818-40-2 ]
Reference: [1] Journal of Antibiotics, 1976, vol. 29, # 9, p. 890 - 901
  • 19
  • [ 54713-12-1 ]
  • [ 103-82-2 ]
  • [ 54582-01-3 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1729 - 1735
  • 20
  • [ 72500-37-9 ]
  • [ 22818-40-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 721 - 728
[2] Agricultural and Biological Chemistry, 1987, vol. 51, # 3, p. 721 - 728
  • 21
  • [ 43189-38-4 ]
  • [ 22818-40-2 ]
Reference: [1] Journal of the Chemical Society. Perkin transactions 1, 1976, # 5, p. 475 - 481
  • 22
  • [ 27460-85-1 ]
  • [ 104-15-4 ]
  • [ 75-05-8 ]
  • [ 762-84-5 ]
  • [ 22818-40-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 11, p. 3333 - 3334
  • 23
  • [ 13253-44-6 ]
  • [ 22818-40-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 355 - 362
  • 24
  • [ 1007-06-3 ]
  • [ 22818-40-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1987, vol. 51, # 2, p. 355 - 362
  • 25
  • [ 104-15-4 ]
  • [ 75-05-8 ]
  • [ 22818-40-2 ]
  • [ 35103-34-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 11, p. 3333 - 3334
  • 26
  • [ 22818-40-2 ]
  • [ 38250-16-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3946 - 3952
[2] Patent: WO2013/33093, 2013, A1,
  • 27
  • [ 24424-99-5 ]
  • [ 22818-40-2 ]
  • [ 69651-48-5 ]
Reference: [1] Tetrahedron, 1983, vol. 39, # 15, p. 2563 - 2570
  • 28
  • [ 6324-01-2 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Patent: US6639103, 2003, B1, . Location in patent: Page/Page column 12-13
[2] Chirality, 2017, vol. 29, # 6, p. 315 - 324
[3] Chinese Journal of Chemistry, 2017, vol. 35, # 7, p. 1037 - 1042
  • 29
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Tetrahedron Asymmetry, 2004, vol. 15, # 12, p. 1933 - 1936
  • 30
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
  • [ 37763-23-8 ]
  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 31
  • [ 54713-12-1 ]
  • [ 103-82-2 ]
  • [ 54582-01-3 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1729 - 1735
  • 32
  • [ 67-56-1 ]
  • [ 22818-40-2 ]
  • [ 37763-23-8 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 10 h; Step 1:To a solution of (R)-2-amino-2-(4-hydroxyphenyl)acetic acid 25a(D-4Hydroxyphenyl glycine, 10.0 g, 60.1 mmol) in methanol (200 mL) was added dropwise thionyl chloride (8 mL) and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuum and the residue was washed twice with ether to yield (Pv)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester 25b (13.0 g, 60.0 mmol, 100percent) as a white solid. 1H NMR (300 MHz, DMSO- 6) ? 3.68 (s, 3 H), 5.07 (s, 1 H), 6.85 (d, J= 8.5 Hz, 2 H), 7.29 (d, J= 8.6 Hz, 2 H), 9.03 (s, 3 H), 10.02 (s, 1 H). Step 2:(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate 25b (©-4-hydroxyphenylglycine methyl ester, 0.302 g, 1.39 mmol) was dissolved in a freshly prepared aqueous solution of glyoxylic acid (1.27 g, 13.8 mmol) and copper(II) sulfate pentahydrate (0.35 g, 1.40 mmol) in a buffer containing 2.5 M pyridine and 0.5 M acetic acid. The mixture was stirred for 10 h at room temperature and then extracted with three portions of methylene chloride (10 mL). The organic layers were combined, washed three times with 0.5 M HC1 (20 mL), dried, filtered and concentrated in vacuum to dryness. The residue was purified by flash column chromatography (silica gel, eluting with chloroform) to yield methyl2- (4-hydroxyphenyl)-2-oxoacetate 25c (0.109 g, 6.06 mmol, 44percent) as a clear oil. 1H NMR (300 MHz, CDCls) ? 3.99 (s, 3 H), 5.41 (br s, 1 H), 6.95 (d, J= 8.8 Hz, 2 H), 8.00 (d, J = 8.8 Hz, 2 H).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3946 - 3952
[2] Patent: WO2013/33093, 2013, A1, . Location in patent: Page/Page column 137; 138
[3] Angewandte Chemie - International Edition, 1997, vol. 37, # 19, p. 2708 - 2714
[4] Organic Letters, 2015, vol. 17, # 4, p. 1018 - 1021
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 4555 - 4568
[6] Tetrahedron Asymmetry, 2000, vol. 11, # 8, p. 1789 - 1796
[7] Chemistry - A European Journal, 1999, vol. 5, # 9, p. 2602 - 2621
[8] Journal of the American Chemical Society, 2004, vol. 126, # 14, p. 4490 - 4491
[9] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 19, p. 5161 - 5169
[10] Organic Letters, 2000, vol. 2, # 16, p. 2459 - 2462
[11] Patent: EP1144368, 2004, B1, . Location in patent: Page 78
[12] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3320 - 3334
[13] Patent: WO2011/113486, 2011, A1, . Location in patent: Page/Page column 7-9
[14] Patent: WO2011/161645, 2011, A1, . Location in patent: Page/Page column 23
[15] Patent: WO2013/129879, 2013, A1, . Location in patent: Page/Page column 74
[16] Patent: WO2018/192462, 2018, A1, . Location in patent: Paragraph 295; 296
  • 33
  • [ 67-56-1 ]
  • [ 1327278-14-7 ]
  • [ 22818-40-2 ]
  • [ 37763-23-8 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 34
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
  • [ 37763-23-8 ]
  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 35
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
  • [ 37763-23-8 ]
  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 22818-40-2 ]

Amino Acid Derivatives

Chemical Structure| 271583-17-6

[ 271583-17-6 ]

2-Amino-2-(2-methoxyphenyl)acetic acid

Similarity: 0.89

Chemical Structure| 127369-30-6

[ 127369-30-6 ]

(S)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

Similarity: 0.89

Chemical Structure| 57591-61-4

[ 57591-61-4 ]

(R)-Methyl 2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

Similarity: 0.89

Chemical Structure| 1212977-59-7

[ 1212977-59-7 ]

(S)-2-Amino-2-(3-ethoxy-4-methoxyphenyl)acetic acid

Similarity: 0.86

Chemical Structure| 2835-06-5

[ 2835-06-5 ]

H-DL-Phg-OH

Similarity: 0.86