[ CAS No. 459-80-3 ] {[proInfo.proName]}

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Quality Control of [ 459-80-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 459-80-3 ]

CAS No. :	459-80-3	MDL No. :	MFCD00036493
Formula :	C₁₀H₁₆O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZHYZQXUYZJNEHD-VQHVLOKHSA-N
M.W :	168.23	Pubchem ID :	5275520
Synonyms :

Safety of [ 459-80-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H312-H315	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 459-80-3 ]

* 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 [ 459-80-3 ]

[ 459-80-3 ] Synthesis Path-Downstream 1~11

1
[ 5392-40-5 ]
[ 459-80-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium chlorite; sodium dihydrogenphosphate In water; <i>tert</i>-butyl alcohol Ambient temperature;
46%	With sodium chlorite; sodium dihydrogenphosphate; dimethyl sulfoxide In water Ambient temperature;
17.4%	With oxygen In dichloromethane at 60℃; for 4h; autoclave;	In a 35-ml steel autoclave was added 3.21 g (20 mmol) Citral (1), 394 mg (0.02mmol Au) catalyst (3) followed by 15 ml Dichloromethane. The suspension was stirred at 250 RPM and heated to 60°C (internal temperature) under oxygen gas (10 bar) for 4 hours. After cooling (2O0C), the catalyst was separated by filtration and the cake rinsed with Dichlromethane. The mother liquor was evaporated under reduced pressure (30 mbar, 4O0C) and the resulting oil analyzed by GC-MS. ResultsWeight: 3.07 gCitral [BIZ) (1): 52.7 % Geranic acid (2): 19.4 %Conversion of 1; 46.9 %Yield of 2: 17.4 %Selectivity: 37.1 %

	With silver(l) oxide
	With silver(l) oxide
	With manganese(IV) oxide In hexane at 0℃; for 0.5h;
	With aldehyde dehydrogenase from pseudomonas putida KT₂₄₄₀; water; nicotinamide adenine dinucleotide phosphate
	With sodium chlorite; sodium dihydrogenphosphate; limonene. In water; <i>tert</i>-butyl alcohol at 15 - 35℃; for 16h;	1.1 Step 1: Using citral as raw material,The modified Pinnick oxidation reaction gives a geranic acid intermediate. specifically:Add citral (100g) and dipentene (446g) to a 5L three-necked flask.Tert-butanol (486 g), 902 g of a 16.8% aqueous solution of sodium dihydrogen phosphate was added.Slowly add 379.6 g of a 20% sodium chlorite solution at 15 ° C.The temperature is not higher than 35 ° C; after the completion of the dropwise addition, the reaction is stirred at room temperature for 16 h;After the raw material is completely reacted, the liquid is separated, and the upper organic phase is separated.The lower aqueous phase was extracted with toluene (2 x 100 mL) and the organic phases were combined.Rotating to remove t-butanol and toluene therein;Then 10% sodium hydroxide solution 400g, stirred for 0.5h,The liquid phase was separated, and the aqueous phase was extracted with toluene (2×100 mL), and the organic phase was discarded.The extracted aqueous phase was adjusted to pH 2.0 with 31% sulfuric acid to separate the organic phase.The aqueous phase was extracted with toluene (2×50 mL), and the organic phases were combined and evaporated.The crude product was 117.8 g, which was geranic acid, and the content was 77.4% (the sum of the two isomers).Directly invest in the next step;

Reference： [1]Bal, Balkrishna S.; Childers, Wayne E.; Pinnick, Harold W. [Tetrahedron, 1981, vol. 37, p. 2091 - 2096]
[2]Dalcanale, Enrico; Montanari, Fernando [Journal of Organic Chemistry, 1986, vol. 51, # 4, p. 567 - 569]
[3]Current Patent Assignee: KONINKLIJKE DSM N.V. - WO2008/148549, 2008, A2 Location in patent: Page/Page column 27-28
[4]Bernhauer; Forster [Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 147, p. 199,201]
[5]Semmler [Chemische Berichte, 1890, vol. 23, p. 3556]
[6]Duettmann,H.; Weyerstahl,P. [Justus Liebigs Annalen der Chemie, 1976, p. 1753 - 1756]
[7]Andersen, John F.; Walding, Jennifer K.; Evans, Philip H.; Bowers, William S.; Feyereisen, Rene [Chemical Research in Toxicology, 1997, vol. 10, # 2, p. 156 - 164]
[8]Winkler, Till; Groeger, Harald; Hummel, Werner [ChemCatChem, 2014, vol. 6, # 4, p. 961 - 964]
[9]Current Patent Assignee: XIAMEN OAMIC BIOTECH CO LTD - CN109053407, 2018, A Location in patent: Paragraph 0048; 0049; 0050

2
[ 106-25-2 ]
[ 459-80-3 ]

Yield	Reaction Conditions	Operation in experiment
38.5%	With sodium hydroxide; oxygen; lead acetate In water at 25℃; for 6h;

Reference： [1]Akada, Mitsuo; Nakano, Shinji; Sugiyama, Toshiyuki; Ichitoh, Kazumoto; Nakao, Hiroki; et al. [Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 5, p. 1511 - 1515]

3
[ 71-44-3 ]
[ 459-80-3 ]
[ 1394833-43-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	Example 1: General procedure for the synthesis of the compounds 1-7 according to the invention; The general synthetic pathway for the preparation of polyaminoisoprenyl derivatives 1-7 of the invention can be illustrated by the example below which represents the preparation of compound 7 (yield: 75% by weight).; In a 50 mL two necked round flask were placed at room temperature under argon geranic acid (250 mg, 1.5 10"3 mol) and spermine (303 mg, 1.5 10"3 mol) in anhydrous CH2CI2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (200 muL, 1.5 10"2 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 mug, 1.5 10"3 mol) dissolved in 5 mL of anhydrous CH2CI2. The reaction was stirred for 12 hours at 20C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CTLCVMeOH/ H4OH (7/3/1) eluent affording the expected coupling product 7 in 75% yield.Compound 7, Yellow solid; 1H MR (MeOD): <5 = 5.49-5.21 (m, 2H), 3.51 (m, 2H), 2.71- 2.03 (m, 24H), 1.74-1.61 (m, 12H). 13C (MeOD): <5 = 170.41, 153.39, 133.58, 124.96, 119.62, 56.40, 54.04, 50.56, 47.96, 45.92, 42.21, 38.00, 30.22, 28.33, 27.68, 26.36, 25.69, 19.02, 18.25. C20H40N4O m/z 353.3275 (100%, (M+H+))
69%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: In a 50 mL two necked round flask were placed at room temperature under argon geranic acid 1 (250 mg, 1.5 × 10-3 mol) and 1,2-ethylenediamine (90 mg, 1.5 × 10-3 mol) in anhydrous CH2Cl2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (195 muL, 1.5 × 10-3 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 mug, 1.5 × 10-3 mol) dissolved in 5 mL of anhydrous CH2Cl2. The reaction was stirred for 12 h at 20 C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CH2Cl2/MeOH/NH4OH (7:3:1) eluent affording the expected coupling product 3 in 75% yield.

Reference： [1]Patent: WO2012/113891,2012,A1 .Location in patent: Page/Page column 23
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1174 - 1179

4
[ 7663-77-6 ]
[ 459-80-3 ]
[ 1394833-65-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	4.2 General procedure for the synthesis of the compounds 3-14 General procedure: In a 50 mL two necked round flask were placed at room temperature under argon geranic acid 1 (250 mg, 1.5 × 10-3 mol) and 1,2-ethylenediamine (90 mg, 1.5 × 10-3 mol) in anhydrous CH2Cl2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (195 μL, 1.5 × 10-3 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 μg, 1.5 × 10-3 mol) dissolved in 5 mL of anhydrous CH2Cl2. The reaction was stirred for 12 h at 20 °C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CH2Cl2/MeOH/NH4OH (7:3:1) eluent affording the expected coupling product 3 in 75% yield.

Reference： [1]Brunel, Jean Michel; Lieutaud, Aurélie; Lome, Vincent; Pagès, Jean-Marie; Bolla, Jean-Michel [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1174 - 1179]

5
[ 123-00-2 ]
[ 459-80-3 ]
[ 1394833-66-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: In a 50 mL two necked round flask were placed at room temperature under argon geranic acid 1 (250 mg, 1.5 × 10-3 mol) and 1,2-ethylenediamine (90 mg, 1.5 × 10-3 mol) in anhydrous CH2Cl2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (195 muL, 1.5 × 10-3 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 mug, 1.5 × 10-3 mol) dissolved in 5 mL of anhydrous CH2Cl2. The reaction was stirred for 12 h at 20 C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CH2Cl2/MeOH/NH4OH (7:3:1) eluent affording the expected coupling product 3 in 75% yield.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1174 - 1179

6
[ 2783-17-7 ]
[ 459-80-3 ]
[ 1394833-42-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: In a 50 mL two necked round flask were placed at room temperature under argon geranic acid 1 (250 mg, 1.5 × 10-3 mol) and 1,2-ethylenediamine (90 mg, 1.5 × 10-3 mol) in anhydrous CH2Cl2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (195 muL, 1.5 × 10-3 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 mug, 1.5 × 10-3 mol) dissolved in 5 mL of anhydrous CH2Cl2. The reaction was stirred for 12 h at 20 C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CH2Cl2/MeOH/NH4OH (7:3:1) eluent affording the expected coupling product 3 in 75% yield.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1174 - 1179

7
[ 459-80-3 ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
C₅₁H₈₈N₁₄O₉ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 625 - 639

8
[ 459-80-3 ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
C₇₁H₁₁₉N₁₃O₁₈ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 625 - 639

9
[ 459-80-3 ]
[ 17364-16-8 ]
1'-palmitoyl-2'-geranoyl-sn-glycero-3'-phosphocholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 40℃; for 72h;Inert atmosphere; Darkness;	General procedure: Terpene acids (1a or 1b, 0.604 mmol), solution of DMAP (74 mg, 0.6 mmol) in 3 mL of CH2Cl2 and finally a solution of DCC (267 mg, 1.3 mmol) in 5 mL of CH2Cl2 were added to the solution of 1-palmitoyl-2-hydroxy-sn-3-glycero-phosphocholine (6)(150 mg, 0.302 mmol) dissolved in 4 mL of anhydrous CH2Cl2. The reaction was carried out for 72 h under a nitrogen atmosphere in the dark at 40C. The product was extracted according to the method described for compound 3a and 3b. 1-Palmitoyl-2-isoprenoyl-sn-glycero-3-phosphocholine (7) was obtained as the mixture of two stereoisomers.

Reference： [1]PLoS ONE,2016,vol. 11

10
[ 502-65-8 ]
[ 459-80-3 ]

Yield	Reaction Conditions	Operation in experiment
1.036 g	With oxygen; In ethyl acetate; at 68℃; for 21h;	Lycopene (817 mg) was placed in a 3-neck flask with stir bar, reflux condenser and 02 inlet (Pasteur pipette). Ethyl acetate (20.4 mL) was added, 02 was bubbled through and the stirred mixture was lowered into an oil bath at 68C. After 21 h, the reaction was stopped and the slightly cloudy yellow liquid was cooled to room temp. The absorbance of a filtered sample was measured as 0.272 at 380 nm in a 1 cm cuvette at ca. 1.0 g/L. The cloudy yellow liquid was centrifuged, the supernatant decanted and the solid residue rinsed/centrifuged with ethyl acetate (2 3 mL), decanting the supernatant each time. The solid residue was dried under vacuum for 4 h to give a pale yellow, flaky solid (38 mg). The combined supernatant liquids were transferred to a 50 mL round bottom flask and solvent was removed on the rotary- evaporator at 40 C down to a pressure of 30 mm Hg. The residue was transferred to a vacuum pump and dried for 4 h to give a foam-like, yellow solid (1.036 g) as OxLyc.

Reference： [1]Patent: WO2017/143460,2017,A1 .Location in patent: Paragraph 00107

11
[ 459-80-3 ]
[ 23696-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: phosphoric acid / toluene / 8 h / 100 °C 2.1: thionyl chloride / toluene / Reflux 2.2: 6 h / 145 - 150 °C / Inert atmosphere 3.1: magnesium / tetrahydrofuran / 1 h / 20 - 42 °C 3.2: 1 h / 25 °C 3.3: 12 h / Inert atmosphere; Reflux 4.1: sodium acetate; peracetic acid / water; dichloromethane / 10 - 25 °C 5.1: potassium carbonate / methanol / 5.5 h / Inert atmosphere; Reflux 6.1: toluene-4-sulfonic acid / dichloromethane / 12 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: XIAMEN OAMIC BIOTECH CO LTD - CN109053407, 2018, A

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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. 459-80-3 ] {[proInfo.proName]}

Quality Control of [ 459-80-3 ]

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[ 459-80-3 ] Synthesis Path-Downstream 1~11

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