[ CAS No. 56-53-1 ] {[proInfo.proName]}

Name: 56-53-1|(E)-4,4'-(Hex-3-ene-3,4-diyl)diphenol|98%
Brand: Ambeed
SKU: A174248
Rating: 93 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

2D 3D

Structure of 56-53-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 56-53-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 56-53-1 ]

SDS Specification

Alternatived Products of [ 56-53-1 ]

Product Details of [ 56-53-1 ]

CAS No. :	56-53-1	MDL No. :
Formula :	C₁₈H₂₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RGLYKWWBQGJZGM-ISLYRVAYSA-N
M.W :	268.35	Pubchem ID :	448537
Synonyms :	Stilbestrol

Calculated chemistry of [ 56-53-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	85.09
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.74
Log Po/w (XLOGP3) :	5.07
Log Po/w (WLOGP) :	4.83
Log Po/w (MLOGP) :	3.86
Log Po/w (SILICOS-IT) :	4.25
Consensus Log Po/w :	4.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.88
Solubility :	0.00355 mg/ml ; 0.0000132 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.66
Solubility :	0.000584 mg/ml ; 0.00000218 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.44
Solubility :	0.000977 mg/ml ; 0.00000364 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 56-53-1 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P202-P264-P270-P280-P301+P312-P308+P313-P330-P403-P501	UN#:	3077
Hazard Statements:	H302-H350-H411	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 56-53-1 ]

* 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 [ 56-53-1 ]
Downstream synthetic route of [ 56-53-1 ]

[ 56-53-1 ] Synthesis Path-Upstream 1~2

1
[ 56-53-1 ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1] Chemische Berichte, 1941, vol. 74, p. 777,782
[2] Journal of Organic Chemistry, 1944, vol. 9, p. 175
[3] Journal of Organic Chemistry, 1944, vol. 9, p. 175
[4] Patent: US2421402, 1945, ,

2
[ 56-53-1 ]
[ 84-16-2 ]

Reference： [1] Patent: US2421401, 1944, ,
[2] Patent: GB596095, 1945, ,

[ 56-53-1 ] Synthesis Path-Downstream 1~18

1
[ 56-53-1 ]
[ 84-16-2 ]

Reference： [1]Patent: US2421401,1944,
[2]Patent: GB596095,1945,

2
[ 56-53-1 ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1]Chemische Berichte,1941,vol. 74,p. 777,782
[2]Journal of Organic Chemistry,1944,vol. 9,p. 175
[3]Journal of Organic Chemistry,1944,vol. 9,p. 175
[4]Patent: US2421402,1945,

3
[ 130-79-0 ]
[ 56-53-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: Diethylstilbestrol dimethyl ether With boron tribromide In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: With water In dichloromethane at 0℃; for 0.5h;	2 4.2.2. (E)-4,40-(Hex-3-ene-3,4-diyl)diphenol (2) The solution of (E)-4,4'-(hex-3-ene-3,4-diyl)bis(methoxybenzene) (1) (6.42 g, 22.0 mmol) in dry CH2Cl2 (150 mL) was cooled to -78 °C and then BBr3 (6.36 mL, 66.0 mmol) was added dropwise under argon atmosphere. The mixture was then stirred for 2 h at room temperature and poured into the mixture of ice/H2O (350 mL). The mixture was stirred for 30 min and extracted with CH2Cl2 (2 * 200 mL). Combined organic phases were washed with brine (1 * 300 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was then purified by column chromatography with ethyl acetate/hexane as an eluent to afford compound 2 as an off-white solid. Yield: 3.66 g (63%); IR (ATR) ν 3405, 2975, 2931, 1608, 1589, 1509, 1426, 1335, 1245, 1199, 1171, 829, 805 cm-1; 1H NMR (400 MHz, DMSO-d6) δ 0.71 (t, 6H, J = 7.4 Hz, 2 * CH3), 2.07 (q, 4H, J = 7.4 Hz, 2 * CH2), 6.74-6.79 (m, 4H, 4 * Ar-H), 6.96-7.01 (m, 4H, 4 * Ar-H), 9.33 (s, 2H, 2 * OH) ppm; 13C NMR (101 MHz, DMSO-d6) δ 13.32 (2C), 28.03 (2C), 114.85 (4C), 129.30 (4C), 132.48 (2C), 137.93 (2C), 155.68 (2C) ppm. HRMS m/z for C18H20O2 ([M + H+]+): calcd 269.1542; found 269.1545. HPLC: Method B, retention time: 14.93 min (99.9% at 254 nm).
50.2%	With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane at 83.5℃; for 576h;
	With potassium hydroxide; Dipropylene glycol at 215 - 235℃;

	With potassium hydroxide at 200℃;
	With potassium hydroxide at 200 - 210℃;
	With potassium hydroxide; ethylene glycol at 180 - 215℃;
	With potassium hydroxide; diethylene glycol at 215 - 235℃;
	With potassium hydroxide at 200 - 210℃;

Reference： [1]Hodnik, Žiga; Tomašič, Tihomir; Smodiš, Domen; D'Amore, Claudio; Mašič, Lucija Peterlin; Fiorucci, Stefano; Kikelj, Danijel [European Journal of Medicinal Chemistry, 2015, vol. 103, p. 551 - 562]
[2]Williard, Paul G.; Fryhle, Craig B. [Tetrahedron Letters, 1980, vol. 21, p. 3731 - 3734]
[3]Current Patent Assignee: ELI LILLY & CO - US2325307, 1941, A Current Patent Assignee: BURTON T BUSH - US2410463, 1943, A
[4]Peteri [Journal of the Chemical Society, 1940, p. 833]
[5]Dodds et al. [Proceedings of the Royal Society of London. Series B, Biological sciences, 1939, vol. 127, p. 140,153 Anm. 154][Proceedings of the Royal Society of London, 1944, vol. 132, p. 83,91] Current Patent Assignee: SANOFI - DE717653, 1939, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.]
[6]Current Patent Assignee: BURTON T BUSH - US2410463, 1943, A
[7]Current Patent Assignee: ELI LILLY & CO - US2325307, 1941, A Current Patent Assignee: BURTON T BUSH - US2410463, 1943, A
[8]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2248019, 1940, A

4
[ 56-53-1 ]
[ 123-62-6 ]
[ 130-80-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 25℃;
	With pyridine
	With pyridine Ambient temperature;

Reference： [1]Wessely et al. [Monatshefte fur Chemie, 1948, vol. 79, p. 596,702]
[2]Dodds et al. [Proceedings of the Royal Society of London. Series B, Biological sciences, 1939, vol. 127, p. 140,153 Anm. 154][Proceedings of the Royal Society of London, 1944, vol. 132, p. 83,91] Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - GB531178, 1939, A Current Patent Assignee: I.G. FARBENINDUSTRIE AG (historic) - DE738521, 1938, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - CH225257, 1938, A
[3]Marson,L.M. [Bollettino Chimico Farmaceutico, 1963, vol. 102, p. 317 - 321]
[4]Inamori; Kubo; Ogawa; Moriwaki; Tsujibo; Baba; Kozawa [Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 10, p. 4478 - 4483]
[5]Current Patent Assignee: CIBA PHARMACEUTICAL PRODUCTS, INC. - US2353684, 1939, A

5
[ 56-53-1 ]
[ 91318-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diclazuril; deuteromethanol In water-d2 at 85℃; for 216h;
82.5 %	With ruthenium trichloride; 10 % platinum on carbon; 10% Pd/C; water-d2; caesium carbonate In tetrahydrofuran at 60℃; Autoclave; Inert atmosphere;	1-3 A synthetic method of deuterium-labeled diethylstilbestrol, comprising the steps of: (1)2.68g diethylstilbestrol is placed in the autoclave; (2)adding a mixed solvent and ultrasonically dissolving it, specifically, the mixed solvent is 20g deuterium water and 20g tetrahydrofuran; (3)After nitrogen bubbling to remove oxygen, add mixed metal catalyst and strong base catalyst, specifically, described mixed metal catalyst is: 1.06g 10% palladium carbon, 1.95g 10% platinum carbon and 0.104g anhydrous ruthenium chloride ; Specifically, the strong base catalyst is 0.325g cesium carbonate; (4) After stirring and mixing evenly, place it at 60°C and 2 atmospheric pressure for 1 hour; (5) Post-treatment: After cooling down to room temperature, add hydrochloric acid to adjust the pH of the solution to 6-7, filter through diatomaceous earth, extract 3 times with 50 mL of dichloromethane, combine the organic phases, and wash once with saturated brine. Then dry it overnight with anhydrous sodium sulfate, filter it with suction, concentrate, and pass through a chromatography column. The elution solvent is n-hexane:ethyl acetate 4:1, Finally, 2.21 g of the target product with the structure shown in formula (I) was obtained with a yield of 82.5%. According to the analysis of the purity and isotope abundance detection method, the chromatographic purity of the product is 99.3%, and the isotope abundance is 99.1%. This invention has remarkable effects.

Reference： [1]Oda; Sato; Kodama; Saito [Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2397 - 2399]
[2]Current Patent Assignee: FOCUSED PHOTONICS (HANGZHOU), INC. - CN115353443, 2022, A Location in patent: Paragraph 0062-0093

6
[ 110-98-5 ]
[ 130-79-0 ]
KOH [ No CAS ]
[ 56-53-1 ]

Reference： [1]Patent: US2325307,1941,

7
[ 67-56-1 ]
[ 56-53-1 ]
Raney nickel [ No CAS ]
[ 84-16-2 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 2629,2631

8
[ 56-53-1 ]
[ 10034-85-2 ]
[ 64-19-7 ]
red phosphorus [ No CAS ]
[ 84-16-2 ]

Reference： [1]Patent: US2421401,1944,

9
[ 56-53-1 ]
nickel-aluminium-alloy [ No CAS ]
aqueous NaOH [ No CAS ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1]Journal of Organic Chemistry,1944,vol. 9,p. 175

10
[ 56-53-1 ]
[ 67-64-1 ]
palladium/charcoal [ No CAS ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1]Proceedings of the Royal Society of London. Series B, Biological sciences,1939,vol. 127,p. 140,153 Anm. 154
Proceedings of the Royal Society of London,1944,vol. 132,p. 83,91

11
[ 56-53-1 ]
[ 64-19-7 ]
palladium [ No CAS ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1]Chemische Berichte,1941,vol. 74,p. 777,782

12
[ 67-56-1 ]
[ 56-53-1 ]
Raney nickel [ No CAS ]
disodium-salt of 4,4'-dihydroxy-α.α'-diethyl-<i>trans</i>-stilbene [ No CAS ]
[ 84-16-2 ]
[ 84-16-2 ]

Reference： [1]Journal of Organic Chemistry,1945,vol. 10,p. 307,312

13
[ 741270-61-1 ]
[ 56-53-1 ]
[ 29753-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	With water In dimethylsulfoxide-d6 at 110℃;

Reference： [1]Lee, Kangwon; Ki, Chang Do; Kim, Hasuck; Chang, Ji Young [Macromolecules, 2004, vol. 37, # 15, p. 5544 - 5549]

14
[ 927-68-4 ]
[ 56-53-1 ]
(E)-((hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl) diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With caesium carbonate; In acetone; at 60℃; for 48h;	General procedure: To the solution of (E)-4,40-(hex-3-ene-3,4-diyl)diphenol (2) (134 mg, 0.5 mmol) in acetone (20 mL) were added cesium carbonate (489 mg, 1.5 mmol) and 2-<strong>[927-68-4]bromoethyl acetate</strong> (116 mL, 1.05 mmol) or 4-bromobutyl acetate (152 mL, 1.05 mmol). The mixture was stirred at 60 C for 48 h, concentrated in vacuo and dissolved in ethyl acetate (50 mL). Solution was washed with 10% citric acid (250 mL) and brine (150 mL). Organic phase was dried over Na2SO4 and concentrated under reduced pressure. Crude product was then purified by column chromatography with dichloromethane/methanol (40:1) as an eluent to afford compound 3 or 5. 4.2.3.1 (E)-((Hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))bis(ethane-2,1-diyl) diacetate (3) Yield: 183 mg (83%); white solid; IR (ATR) nu2958, 2929, 2869, 1736, 1607, 1508, 1466, 1368, 1233, 1176, 1047, 960, 821 cm-1; 1H NMR (400 MHz, CDCl3) delta 0.78 (t, 6H, J = 7.4 Hz, 2 * CH3), 2.14 (q, 4H, J = 7.4 Hz, 2 * CH2), 2.14 (s, 6H, 2 * CH3), 4.20-4.25 (m, 4H, 2 * CH2), 4.45-4.49 (m, 4H, 2 * CH2), 6.92-6.97 (m, 4H, 4 * Ar-H), 7.12-7.17 (m, 4H, 4 * Ar-H) ppm; 13C NMR (101 MHz, CDCl3) delta 13.39 (2C), 20.97 (2C), 28.58 (2C), 62.98 (2C), 65.86 (2C), 114.08 (4C), 129.81 (4C), 135.53 (2C), 138.71 (2C), 156.88 (2C), 171.10 (2C) ppm. HRMS m/z for C26H32O6 ([M + H+]+): calcd 441.2277; found 441.2271. Elemental analysis calculated (%) for C26H32O6: C 70.89, H 7.32. Found: C: 70.79, H 7.43.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 551 - 562

15
[ 4753-59-7 ]
[ 56-53-1 ]
(E)-((hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))bis(butane-4,1-diyl) diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With caesium carbonate In acetone at 60℃; for 48h;	2 4.2.3. Synthesis of compounds 3 and 5 General procedure: To the solution of (E)-4,40-(hex-3-ene-3,4-diyl)diphenol (2) (134 mg, 0.5 mmol) in acetone (20 mL) were added cesium carbonate (489 mg, 1.5 mmol) and 2-bromoethyl acetate (116 mL, 1.05 mmol) or 4-bromobutyl acetate (152 mL, 1.05 mmol). The mixture was stirred at 60 °C for 48 h, concentrated in vacuo and dissolved in ethyl acetate (50 mL). Solution was washed with 10% citric acid (250 mL) and brine (150 mL). Organic phase was dried over Na2SO4 and concentrated under reduced pressure. Crude product was then purified by column chromatography with dichloromethane/methanol (40:1) as an eluent to afford compound 3 or 5. 4.2.3.2 (E)-((Hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))bis(butane-4,1-diyl) diacetate (5) Yield: 213 mg (86%); white solid; IR (ATR) ν 2982, 2953, 2929, 2869, 1732, 1608, 1531, 1472, 1364, 1241, 1178, 1060, 1034, 949, 841, 810 cm-1; 1H NMR (400 MHz, CDCl3) δ 0.79 (t, 6H, J = 7.4 Hz, 2 * CH3), 1.83-1.95 (m, 8H, 4 * CH2), 2.08 (s, 6H, 2 * CH3), 2.15 (q, 4H, J = 7.4 Hz, 2 * CH2), 4.04 (t, 4H, J = 6.0 Hz, 2 * CH2), 4.18 (t, 4H, J = 6.0 Hz, 2 * CH2), 6.88-6.93 (m, 4H, 4 * Ar-H), 7.11-7.15 (m, 4H, 4 * Ar-H) ppm; 13C NMR (101 MHz, CDCl3) δ 13.43 (2C), 21.03 (2C), 25.45 (2C), 25.98 (2C), 28.59 (2C), 64.21 (2C), 67.16 (2C), 113.89 (4C), 129.74 (4C), 135.06 (2C), 138.72 (2C), 157.32 (2C), 171.26 (2C) ppm. HRMS m/z for C30H40O6 ([M + H+]+): calcd 497.2903; 497.2895 found. Elemental analysis calculated (%) for C30H40O6: C 72.55, H 8.12. Found: C: 72.28, H 8.28.

16
[ 56-53-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: diethylstilbestrol With chlorosulfonic acid In pyridine at -16 - 20℃; for 24h; Inert atmosphere; Stage #2: With sodium hydroxide In pyridine; water at 0 - 20℃; for 24h; Inert atmosphere;	1 4.2.6. Synthesis of compounds 9-12 General procedure: Compound 2, 6, 7 or 8 (0.25 mmol) was dissolved in anhydrous pyridine (10 mL) under argon atmosphere and the solution was cooled to 16 °C. Chlorosulfonic acid (330mL, 5.0 mmol) was added dropwise and the yellow suspension was stirred at room temperature for 24 h. The suspension was cooled to 0 °C and the pH was adjusted to 10 with 5 M NaOH(aq). Reaction mixture was then stirred for 24 h at room temperature and concentrated under reduced pressure. The solid residue was washed with the mixture of methanol and ethanol (1:1) (430 mL) and the combined organic phases were concentrated in vacuo. The crude product was purified by reversed-phase column chromatography with methanol/water as an eluent to afford compounds 9-12. 4.2.6.1 Sodium (E)-hex-3-ene-3,4-diylbis(4,1-phenylene) bis(sulfate) (9) Prepared from (E)-4,4'-(hex-3-ene-3,4-diyl)diphenol (2) (66 mg, 0.25 mmol) according to general procedure. Yield: 81 mg (69%); off-white solid; IR (ATR) ν 3567, 2974, 2959, 2359, 2338, 1499, 1250, 1201, 1044, 1014, 861 cm-1; 1H NMR (400 MHz, DMSO-d6) δ 0.74 (t, 6H, J = 7.4 Hz, 2 * CH3), 2.10 (q, 4H, J = 7.4 Hz, 2 * CH2), 7.08-7.14 (m, 4H, 4 * Ar-H), 7.15-7.21 (m, 4H, 4 * Ar-H) ppm; 13C NMR (101 MHz, DMSO-d6) δ 13.23 (2C), 28.03 (2C), 120.06 (4C), 128.70 (4C), 136.49 (2C), 138.08 (2C), 151.92 (2C) ppm. HRMS m/z for C18H18Na2O8S2 ([M-Na+]-): calcd 449.0341; found 449.0333. HPLC: Method A, retention time: 15.69 min (95.7% at 254 nm).

17
[ 628-09-1 ]
[ 56-53-1 ]
(E)-((hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))bis(propane-3,1-diyl) diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		(E)-4,4'-(Hex-3-ene-3,4-diyl)diphenol (2) (188 mg, 0.7 mmol) was dissolved in DMF (15 mL) and cooled to 0 C. 95% sodium hydride (32 mg, 1.4 mmol) was added and the solution was stirred for 30 min at room temperature. Reaction mixture was cooled to 0 C again and 3-<strong>[628-09-1]chloropropyl acetate</strong> (180 muL, 1.47 mmol) was added. The mixture was stirred for 18 h at 60 C, concentrated in vacuo and suspended in ethyl acetate (50 mL). Suspension was washed with water (1 * 40 mL), 10% citric acid (1 * 40 mL) and brine (1 * 40 mL). Organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was then purified by column chromatography with dichloromethane/methanol (40:1) as an eluent to afford 4 as white solid. Yield: 200 mg (61%); IR (ATR) nu 2950, 2929, 2869, 1739, 1607, 1510, 1467, 1367, 1230, 1175, 1046, 960, 821 cm-1; 1H NMR (400 MHz, CDCl3) delta 0.79 (t, 6H, J = 7.4 Hz, 2 * CH3), 2.10 (s, 6H, 2 * CH3), 2.11-2.18 (m, 8H, 4 * CH2), 4.10 (t, 4H, J = 6.2 Hz, 2 * CH2), 4.31 (t, 4H, J = 6.2 Hz, 2 * CH2), 6.89-6.94 (m, 4H, 4 * Ar-H), 7.11-7.16 (m, 4H, 4 * Ar-H) ppm; 13C NMR (101 MHz, CDCl3) delta 13.43 (2C), 21.02 (2C), 28.60 (2C), 28.71 (2C), 61.41 (2C), 64.19 (2C), 113.92 (4C), 129.75 (4C), 135.18 (2C), 138.72 (2C), 157.18 (2C), 171.14 (2C) ppm. HRMS m/z for C28H36O6 ([M + H+]+): calcd 469.2590; found 469.2579. Elemental analysis calculated (%) for C28H36O6: C 71.77, H 7.74. Found: C: 71.56, H 7.81.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 551 - 562

18
[ 56-53-1 ]
[ 2800928-63-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
50%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 16h;	Compounds 4-28; General Procedure for the Phenolic PharmaceuticalScope of the Prodrug Synthesis Reaction General procedure: To an oven-dried 8-mL vial equipped with a magnetic stir bar wasadded phosphoramidate (0.24 mmol, 1.2 equiv), phenolic drug (0.2mmol, 1.0 equiv), and anhydrous CH3CN (1 mL). Then, DBU (60 L, 0.4mmol, 2.0 equiv) was added via microsyringe. After stirring at 25 °Cfor 16 h, the reaction mixture was diluted with EtOAc (~5 mL), followedby the addition of 1 M HCl or H2O (2 mL). The organic layer wasseparated, and the aqueous layer was extracted with EtOAc (2 × 2 mL).The combined organic layer was filtered through a pad of anhydrousNa2SO4 and concentrated under reduced pressure to afford crudeproduct. The residue was purified by silica gel column chromatographyto give the target product. Methyl N-((2,6-Diisopropylphenoxy)(ethoxy)phosphoryl)glycinate(4)After purification by silica gel column chromatography (25-50% EtOAcin PE), the title compound was isolated as a yellow oil (60.2 mg, 84%yield).1H NMR (500 MHz, CDCl3): = 7.12 (s, 3 H), 4.12 (p, J = 7.2 Hz, 2 H),3.92-3.85 (m, 1 H), 3.83-3.77 (m, 1 H), 3.76 (s, 3 H), 3.53-3.44 (m, 2H), 3.42-3.37 (m, 1 H), 1.28 (t, J = 7.1 Hz, 3 H), 1.22 (t, J = 6.9 Hz, 12 H).13C NMR (126 MHz, CDCl3): = 171.32 (d, JC-P = 8.6 Hz), 145.72 (d, JC-P =9.0 Hz), 140.73 (d, JC-P = 3.2 Hz), 125.61 (d, JC-P = 1.9 Hz), 124.22 (d, JC-P =1.8 Hz), 63.45 (d, JC-P = 5.2 Hz), 52.48, 43.20 (d, JC-P = 1.8 Hz), 27.10,23.66 (d, JC-P = 3.8 Hz), 16.17 (d, JC-P = 7.0 Hz).31P NMR (203 MHz, CDCl3): = 2.51.HRMS (ESI): m/z calcd for C17H29NO5P+ [M + H]+: 358.1778; found:358.1779.

Reference： [1]Yao, Jie; Huang, Chengjie; Wu, Fan; Zhao, Yufen; Ni, Feng [Synthesis, 2022, vol. 54, # 13, p. 3005 - 3014]

Same Skeleton Products

Related Products

Historical Records

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 56-53-1 ] {[proInfo.proName]}

Quality Control of [ 56-53-1 ]

Related Doc. of [ 56-53-1 ]

Product Details of [ 56-53-1 ]

Calculated chemistry of [ 56-53-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 56-53-1 ]

Application In Synthesis of [ 56-53-1 ]

[ 56-53-1 ] Synthesis Path-Upstream 1~2

[ 56-53-1 ] Synthesis Path-Downstream 1~18

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry