37905-02-5|(2E,6E)-3,7-Dimethyl-8-oxoocta-2,6-dien-1-yl acetate| Ambeed

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Quality Control of [ 37905-02-5 ] Purity: 98% SDS Specification

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Product Details of [ 37905-02-5 ]

CAS No. :	37905-02-5
Formula :	C₁₂H₁₈O₃
M.W :	210.27
SMILES Code :	CC(OC/C=C(CC/C=C(C=O)\C)\C)=O
MDL No. :	MFCD31922286
InChI Key :	YODDEHYDMMDDCV-NXAIOARDSA-N
Pubchem ID :	10058953

Safety of [ 37905-02-5 ]

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

Application In Synthesis of [ 37905-02-5 ]

* 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.

Downstream synthetic route of [ 37905-02-5 ]

[ 37905-02-5 ] Synthesis Path-Downstream 1~35

1
[ 105-87-3 ]
[ 37905-02-5 ]

Yield	Reaction Conditions	Operation in experiment
41%	With selenium(IV) oxide; In ethanol; for 22h;Reflux;	Geranyl acetate (7) (6.84 g, 34.9 mmol) pre-dissolved in 100 mL of 95% ethanol was added dropwise over 40 min to a refluxing solution of SeO2(5.8 g, 52 mmol) in 300 mL of 95% ethanol. The mixture was heated under reflux for 22 h. The black precipitate was removed by vacuum filtration over a pad of silica-gel, and washed with 95% ethanol. Solvent was removed at reduced pressure, and 400 mL of ethyl ether was added. Organic layer was washed with brine (4×80 mL), dried overNa2SO4, and concentrated under vacuum. The residue was purified byusing silica gel column chromatography to give a light yellow oil(2.8 g) with a yield of 41%.
24%	In ethanol;	Next, the carbon atom at position 8 was subjected to selenium oxidation in ethanol to obtain an aldehyde form (compound represented by (bii) below) (yield: 24%).
		Example 8General Preparation of Lycophyll 2HCrocetindialdehyde (238) was obtained from SynChem, Inc. (Des Plaines, Ill.) as a brick-red solid and was used without further purification. Lycopene was obtained from ChromaDex (Santa Ana, Calif.) as a red solid and was used without further purification. Acetic acid 3,7-dimethyl-8-oxo-octa-2,6-dienyl ester (230a) (Liu and Prestwich 2002) was synthesized by literature procedures from commercially available geranyl acetate (228a). All other reagents and solvents used were purchased from Across Organics (Morris Plains, N.J.) and Sigma-Aldrich (St. Louis, Mo.) and were used without further purification. All reactions were performed under a nitrogen atmosphere. All flash chromatographic purifications were performed on Natland International Corporation 230-400 mesh silica gel using indicated solvents. LC/MS (APCI and ESI+modes) were recorded on an Agilent 1100 LC/MSD VL system; column: Zorbax Eclipse XDB-C18 Rapid Resolution (4.6×75 mm, 3.5 μm); temperature: 25'.C; flow rate: 1.0 mL/min.; mobile phase (A=0.025% TFA in H2O, B=0.025% TFA in acetonitrile). Gradient program (for intermediates 230a-236a and 216a): 70% A/30% B (start), step gradient to 50% B over 5 minutes, step gradient to 100% B over 1.3 minutes, hold at 100% B over 4.9 minutes. Gradient program (for intermediates 218a, 2H): 70% A/30% B (start), step gradient to 50% B over 5 minutes, step gradient to 98% B over 3.3 minutes, hold at 98% B over 16.9 minutes. All-trans lycophyll was obtained from crude material using a Waters 996 Photo Diode Array detector, Millipore 600E System Controller and Waters 717 Autosampler; column: YMC C30 Carotenoid S-5, (10×250 mm, 5 μm column); temperature: 25 C.; flow rate: 4.7 mL/min; mobile phase (A=methanol (MeOH), B=methyl-t-butyl ether (MTBE)) Gradient program: 60% A/40% B (start), step gradient to 80% A over 1 minute, hold at 80% A over 119 minutes. Fractions were collected from 55-66 minutes. Fraction analysis was performed on a YMC C30 Carotenoid S-5, (4.6×250 mm, 5 μm column). Proton nuclear magnetic resonance (NMR) spectra were obtained on a Varian Unity INOVA 500 spectrometer operating at 500.111 MHz (megahertz). Electronic absorption spectra were recorded on a Cary 50 Bio UV-Visible spectrophotometer.

	With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; water; for 48h;	Procedure adapted from literature procedures.15 Selenium dioxide (0.742 g, 6.68 mmol, 14mol %) was suspended in 75 ml DCM in a 500 ml round bottom flask. tert-Butyl hydroperoxide (25 ml,186.8 mmol, 2 equiv.; Luperox 70 wt. % in H2O) was added and the reaction was stirred for 30 min generating a clear, biphasic solution. Geranial acetate (20 ml, 93.3 mmol; Alfa Aesar) was added via syringe. A reflux condenser was attached and the reaction was stirred for 48 h without heating. The reaction was diluted with 100 ml MeOH and cooled to 0 C. Sodium borohydride was added slowly until aldehyde not observed by TLC (Rf = 0.52 (2:1 Hex:EtOAc; KMnO4). Solution turned from clear to red toyellow to clear during this process. The reaction was diluted with another 100 ml DCM and 100 ml H2O
	With tert.-butylhydroperoxide; selenium(IV) oxide; silica gel; salicylic acid; In dichloromethane; at 20℃; for 26h;Inert atmosphere;	A suspension of selenium dioxide (5.6 mg, 1.0 mmol) tert-butyl hydroperoxide (0.24 mL, 2.5 mmol), salicylic acid (12 mol%, 16.6 mg) in anhydrous dichloromethane (20 mL) was stirred for 20 min at room temperature, and then silica gel (230-400 mesh, 72.0 mg) was added. After 30 min, the geranyl acetate 9 (196.3 mg,1.0 mmol) was slowly added. The mixture was stirred for 26 h, filtered through Celite, and washed with 10% potassium hydroxide and brine. The extract was dried over Na2SO4 and concentrated under vacuum. The resulting dark orange residue was dissolved in 4 mL of ethanol and cooled to 0 C, and sodium borohydride (37.8 mg, 1.0 mmol) was added in several portions. After 30 min, a saturated solution of NH4Cl (5 mL), brine, and ethyl acetate was added. The mixture was extracted with ethyl acetate and once with dichloromethane, dried, and concentrated. The residue was purified by flash chromatography eluting with hexane/AcOEt (9/1, v/v) to give alcohol 10 as a yellow oil (160.0 mg, 75%). 1H NMR (400 MHz, CDCl3): δ (ppm)5.38-5.28 (m, 2H), 4.55 (2H, d, J 7.2), 3.96 (2H, s), 2.28-2.06 (5H,m), 2.05 (3H, s), 1.70 (3H, s), 1.60 (3H, s).

References: [1]Organic Process Research and Development,2005,vol. 9,p. 830 - 836.
[2]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 3182 - 3186.
[3]Journal of Organic Chemistry,2000,vol. 65,p. 3027 - 3033.
[4]Journal of Chemical Research - Part S,1997,p. 264 - 265.
[5]Tetrahedron Letters,2019,vol. 60.
[6]Tetrahedron,1985,vol. 41,p. 4359 - 4364.
[7]Chemistry Letters,2010,vol. 39,p. 622 - 623.
[8]Organic Letters,2004,vol. 6,p. 775 - 777.
[9]Journal of the Chemical Society. Perkin transactions I,1981,p. 761 - 769.
[10]Journal of Organic Chemistry,2007,vol. 72,p. 9291 - 9297.
[11]Biochimica et Biophysica Acta - General Subjects,2013,vol. 1830,p. 3635 - 3642.
[12]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 351 - 361.
[13]Patent: US2014/171675,2014,A1 .Location in patent: Paragraph 195-196.
[14]Journal of Agricultural and Food Chemistry,2018,vol. 66,p. 2324 - 2333.
[15]Tetrahedron,1974,vol. 30,p. 715 - 718.
[16]Tetrahedron Letters,1973,p. 281 - 284.
[17]Journal of the American Chemical Society,1977,vol. 99,p. 5526 - 5528.
[18]Journal of the Chemical Society. Chemical communications,1972,p. 486 - 487.
[19]Journal of Organic Chemistry,1990,vol. 55,p. 5088 - 5107.
[20]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2639 - 2651.
[21]Chemistry Letters,1985,p. 1395 - 1398.
[22]Journal of Organic Chemistry,1997,vol. 62,p. 1912 - 1913.
[23]Synlett,1997,vol. 1997,p. 899 - 902.
[24]Journal of Chemical Ecology,1996,vol. 22,p. 729 - 738.
[25]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 221 - 228.
[26]Organic Letters,2003,vol. 5,p. 4843 - 4846.
[27]Journal of Organic Chemistry,1999,vol. 64,p. 807 - 818.
[28]Heterocycles,1998,vol. 47,p. 139 - 142.
[29]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 293 - 299.
[30]Journal of Organic Chemistry,1985,vol. 50,p. 3767 - 3774.
[31]Journal of Organic Chemistry,1986,vol. 51,p. 3834 - 3838.
[32]Tetrahedron,1984,vol. 40,p. 3481 - 3490.
[33]Patent: US2008/221377,2008,A1 .Location in patent: Page/Page column 39; 19.
[34]Patent: EP2636663,2013,A1 .
[35]Journal of the American Chemical Society,2014,vol. 136,p. 642 - 645.
[36]Journal of labelled compounds and radiopharmaceuticals,2013,vol. 56,p. 485 - 491.
[37]Synthesis,2018,vol. 50,p. 4343 - 4350.
[38]Tetrahedron,2020,vol. 76.

2
[ 37905-02-5 ]
[ 37905-03-6 ]

Yield	Reaction Conditions	Operation in experiment
1.517 g	With sodium tetrahydroborate; ethanol; at 0℃; for 1h;	General procedure: SeO2 (602 mg, 5.43 mmol) was added to a solution of geranyl acetate (Compound 29, 1.0 ml, 4.7 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and EtOH (20 ml) was then added to the residue. The mixture was cooled to 0C. NaBH4 (58 mg, 1.5 mmol) was added to this cooled mixture followed by stirring for one hour. A 2 M aqueous HCl solution (2 ml) was added to the reaction solution followed by stirring for 5 minutes. The mixture was then poured into H2O (30 ml). After extraction with EtOAc, the combined organic layer was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was subjected to column chromatography on silica gel (Hexane:EtOAc= 2:1) to yield a partially purified primary alcohol (Compound 30) (1.517 g).
160.0 mg	With sodium tetrahydroborate; In dichloromethane; at 0℃; for 0.5h;Inert atmosphere;	A suspension of selenium dioxide (5.6 mg, 1.0 mmol) tert-butyl hydroperoxide (0.24 mL, 2.5 mmol), salicylic acid (12 mol%, 16.6 mg) in anhydrous dichloromethane (20 mL) was stirred for 20 min at room temperature, and then silica gel (230-400 mesh, 72.0 mg) was added. After 30 min, the geranyl acetate 9 (196.3 mg,1.0 mmol) was slowly added. The mixture was stirred for 26 h, filtered through Celite, and washed with 10% potassium hydroxide and brine. The extract was dried over Na2SO4 and concentrated under vacuum. The resulting dark orange residue was dissolved in 4 mL of ethanol and cooled to 0 C, and sodium borohydride (37.8 mg, 1.0 mmol) was added in several portions. After 30 min, a saturated solution of NH4Cl (5 mL), brine, and ethyl acetate was added. The mixture was extracted with ethyl acetate and once with dichloromethane, dried, and concentrated. The residue was purified by flash chromatography eluting with hexane/AcOEt (9/1, v/v) to give alcohol 10 as a yellow oil (160.0 mg, 75%). 1H NMR (400 MHz, CDCl3): δ (ppm)5.38-5.28 (m, 2H), 4.55 (2H, d, J 7.2), 3.96 (2H, s), 2.28-2.06 (5H,m), 2.05 (3H, s), 1.70 (3H, s), 1.60 (3H, s).

References: [1]Tetrahedron Letters,1984,vol. 25,p. 761 - 764.
[2]Journal of the Chemical Society. Perkin transactions I,1981,p. 761 - 769.
[3]Journal of Agricultural and Food Chemistry,2018,vol. 66,p. 2324 - 2333.
[4]Journal of Organic Chemistry,1990,vol. 55,p. 5088 - 5107.
[5]Journal of the Chemical Society. Chemical communications,1972,p. 486 - 487.
[6]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2639 - 2651.
[7]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 351 - 361.
[8]Journal of Chemical Ecology,1996,vol. 22,p. 729 - 738.
[9]Tetrahedron Letters,2001,vol. 42,p. 2205 - 2208.
[10]Patent: EP2636663,2013,A1 .Location in patent: Paragraph 0250; 0251.
[11]Journal of labelled compounds and radiopharmaceuticals,2013,vol. 56,p. 485 - 491.
[12]Tetrahedron,2020,vol. 76.

3
[ 37905-02-5 ]
[ 38290-51-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In methanol; at 20℃; for 4h;	Ground 296 K2CO3 (0.802 g, 5.803 mmol) was added to a solution of aldehyde 31 (2.226 g, 10.59 mmol) in 18 MeOH (50 ml) at room temperature, was stirred for 4 hours. 32 H2O was added to the reaction solution, which was extracted with EtOAc twice then with Et2O once. The combined organic layer was washed with a saturated aqueous NH4Cl solution then with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 2:1 to 1:2) to yield the corresponding primary alcohol (1.266 g, 71 %).
42%	With water; potassium hydroxide;	Next, the aldehyde was alkaline-hydrolyzed using potassium hydroxide to obtain an alcohol form (compound represented by (ciii) below) (yield: 42%).

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 20 - 21.
[2]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 351 - 361.
[3]Synlett,1997,vol. 1997,p. 899 - 902.
[4]Patent: EP2636663,2013,A1 .Location in patent: Paragraph 0207; 0208.
[5]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1417 - 1429.
[6]Patent: US2014/171675,2014,A1 .Location in patent: Paragraph 197-198.
[7]Tetrahedron,1974,vol. 30,p. 715 - 718.
[8]Organic Letters,2003,vol. 5,p. 4843 - 4846.
[9]Journal of Organic Chemistry,2004,vol. 69,p. 8186 - 8193.
[10]Journal of Organic Chemistry,2007,vol. 72,p. 9291 - 9297.

4
[ 115-22-0 ]
[ 37905-02-5 ]
[ 99477-54-0 ]

References: [1]Tetrahedron,1985,vol. 41,p. 3049 - 3062.

5
[ 106-24-1 ]
[ 37905-02-5 ]

References: [1]Tetrahedron,1985,vol. 41,p. 3049 - 3062.
[2]Chemistry Letters,1986,p. 2035 - 2038.
[3]Patent: US2014/171675,2014,A1 .
[4]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1347 - 1353.
[5]Biochimica et Biophysica Acta - General Subjects,2013,vol. 1830,p. 3635 - 3642.
[6]Chemistry - A European Journal,2015,vol. 21,p. 12396 - 12404.
[7]Tetrahedron Letters,2019,vol. 60.
[8]Tetrahedron,2020,vol. 76.

6
[ 105-87-3 ]
[ 37905-03-6 ]
[ 37905-02-5 ]

Yield	Reaction Conditions	Operation in experiment
45%; 19%	With selenium(IV) oxide; tert-butyl hydroperoxide; In dichloromethane; at 0℃; for 5h;Inert atmosphere;	General procedure: Starting material (1.00 mmol) was added to a solution of selenium dioxide (44 mg, 0.40 mmol) and t-BuOOH (453 mg, 3.10 mmol) in dichloromethane (5 mL) at 0C. After stirring under nitrogen at 0C for a time t (vide infra), the mixture was diluted with ethyl acetate (15 mL), and washed successively with water (2 x 10 mL), saturated NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The organic layer was then dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (hexanes / ethyl acetate).
	With selenium(IV) oxide; In ethanol; for 1h;Reflux;	SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3108 - 3117.
[2]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1417 - 1429.
[3]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 1347 - 1353.
[4]Tetrahedron,2008,vol. 64,p. 4972 - 4978.
[5]Tetrahedron Letters,2001,vol. 42,p. 2205 - 2208.
[6]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 293 - 299.
[7]Tetrahedron Letters,1984,vol. 25,p. 761 - 764.
[8]Journal of the American Chemical Society,2002,vol. 124,p. 20 - 21.
[9]Journal of Organic Chemistry,1986,vol. 51,p. 3834 - 3838.
[10]Helvetica Chimica Acta,1986,vol. 69,p. 1959 - 1970.
[11]Chemistry of Natural Compounds,1993,vol. 29,p. 618 - 621.
Khimiya Prirodnykh Soedinenii,1993,p. 697 - 701.
[12]Journal of Organic Chemistry,1986,vol. 51,p. 3834 - 3838.
[13]Helvetica Chimica Acta,1986,vol. 69,p. 1959 - 1970.
[14]Patent: EP2636663,2013,A1 .Location in patent: Paragraph 0181; 0182.

7
[ 37905-03-6 ]
[ 37905-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; In diethyl ether; for 15h;	SeO2 (4.34 g, 37.9 mmol) was added to a solution of geranyl acetate (Compound 29, 7.7 ml, 36 mmol) in EtOH (20 ml) at room temperature, and the mixture was refluxed for one hour. The reaction solution was allowed to warm to room temperature, and was filtered through celite. The filtrate was concentrated, and the residue was then subjected to column chromatography on silica gel (Hexane:EtOAc = 1:1). The fractions containing alcohol (Compound 30) and aldehyde (Compound 31) were collected. After evaporation of the solvent, the residue was dissolved in Et2O (100 ml). MnO2 (85% purity, 22.5 g, 220 mmol) was added to this solution followed by stirring for 15 hours. The reaction solution was filtered through celite, and the filtrate was washed with a saturated aqueous NaCl solution, and was dried over Na2SO4. After evaporation of the solvent, the residue was purified by column chromatography on silica gel (Hexane:EtOAc = 4:1) to yield the aldehyde (Compound 31) (2.142 g, 28%).

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 293 - 299.
[2]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1417 - 1429.
[3]Journal of Organic Chemistry,1999,vol. 64,p. 807 - 818.
[4]Organic Letters,2003,vol. 5,p. 4843 - 4846.
[5]Chemistry of Natural Compounds,1991,vol. 27,p. 745 - 747.
Khimiya Prirodnykh Soedinenii,1991,p. 844 - 847.
[6]Tetrahedron,1984,vol. 40,p. 3481 - 3490.
[7]Journal of Organic Chemistry,1986,vol. 51,p. 3834 - 3838.
[8]Journal of Organic Chemistry,1985,vol. 50,p. 3767 - 3774.
[9]Heterocycles,1998,vol. 47,p. 139 - 142.
[10]Patent: EP2636663,2013,A1 .Location in patent: Paragraph 0181; 0182.
[11]Journal of the American Chemical Society,2014,vol. 136,p. 642 - 645.

8
[ 37905-02-5 ]
[ 56691-74-8 ]
[ 103905-01-7 ]

References: [1]Chemistry Letters,1985,p. 1883 - 1886.
[2]Journal of Organic Chemistry,1986,vol. 51,p. 3834 - 3838.
[3]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 779 - 780.

9
[ 74514-19-5 ]
[ 37905-02-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3287 - 3288.

10
[ 74514-19-5 ]
[ 37905-02-5 ]
(Z)-8-acetoxy-2,6-dimethyl-2,6-octadienal [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3287 - 3288.

11
Acetic acid (2E,6E)-8-chloro-3,7-dimethyl-octa-2,6-dienyl ester [ No CAS ]
[ 37905-02-5 ]

References: [1]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 3287 - 3288.

12
[ 37905-02-5 ]
[ 26488-97-1 ]

References: [1]Bioorganic and Medicinal Chemistry,1996,vol. 4,p. 351 - 361.

13
[ 37905-02-5 ]
[ 1099-45-2 ]
(2Z,4E,8E)-10-Acetoxy-4,8-dimethyl-deca-2,4,8-trienoic acid ethyl ester [ No CAS ]
[ 180728-43-2 ]

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 6454 - 6455.

14
[ 109-80-8 ]
[ 37905-02-5 ]
[ 220343-93-1 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 9609 - 9612.

15
[ 37905-02-5 ]
[ 100-58-3 ]
[ 221656-69-5 ]

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 807 - 818.

16
[ 37905-02-5 ]
[ 62-53-3 ]
(2E,6Z)-8-aniline-3,7-dimethyl-1-acetoxy-2,6-octadiene [ No CAS ]
(2E,6E)-8-aniline-3,7-dimethyl-1-acetoxy-2,6-octadiene [ No CAS ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 3027 - 3033.

17
[ 37905-02-5 ]
[ 62-53-3 ]
C₁₂H₁₈O₂NHTC₆H₅ [ No CAS ]
C₁₂H₁₈O₂NHTC₆H₅ [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 3602 - 3605.

18
[ 37905-02-5 ]
[ 406486-15-5 ]
[ 406486-16-6 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 2263 - 2266.

19
[ 771-60-8 ]
[ 37905-02-5 ]
[ 447454-15-1 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

20
[ 37905-02-5 ]
[ 100-01-6 ]
[ 447454-14-0 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

21
[ 37905-02-5 ]
[ 147752-43-0 ]
Acetic acid (2E,6E)-8-(5-dimethylsulfamoyl-naphthalen-1-ylamino)-3,7-dimethyl-octa-2,6-dienyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 8186 - 8193.

22
[ 37905-02-5 ]
[ 1779-51-7 ]
[ 406486-12-2 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 2263 - 2266.

23
[ 37905-02-5 ]
[ 56553-60-7 ]
[ 294187-78-3 ]
[ 447454-16-2 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

24
[ 37905-02-5 ]
[ 1877-77-6 ]
C₁₉H₂₇NO₃ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 9291 - 9297.

25
[ 37905-02-5 ]
[ 2450-71-7 ]
C₁₅H₂₃NO₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 9291 - 9297.

26
[ 37905-02-5 ]
[ 138842-85-0 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 8186 - 8193.
[2]Organic Letters,2003,vol. 5,p. 4843 - 4846.
[3]Journal of the American Chemical Society,2002,vol. 124,p. 20 - 21.
[4]Patent: EP2636663,2013,A1 .

27
[ 37905-02-5 ]
[ 447454-18-4 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

28
[ 37905-02-5 ]
[ 447454-21-9 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

29
[ 37905-02-5 ]
[ 447454-19-5 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

30
[ 37905-02-5 ]
[ 447454-22-0 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

31
[ 37905-02-5 ]
[ 447454-20-8 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

32
[ 37905-02-5 ]
[ 447454-23-1 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

33
[ 37905-02-5 ]
C₁₆H₂₁N₂O₂P₂O₇^(3-)*3N(C₄H₉)4⁽¹⁺⁾ [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

34
[ 37905-02-5 ]
C₁₆H₁₇NF₅P₂O₇^(3-)*3(C₄H₉)4N⁽¹⁺⁾ [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

35
[ 37905-02-5 ]
C₁₈H₂₁N₄F₄P₂O₇^(3-)*3(C₄H₉)4N⁽¹⁺⁾ [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 8206 - 8219.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Oxidation States of Sulfur Compounds • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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P282	Wear cold insulating gloves/face shield/eye protection.
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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:
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P320
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P321
P322
P330	Rinse mouth.
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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.
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P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
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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.
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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.
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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

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
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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

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CAS No.: 37905-02-5

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CAS No.: 37905-02-5

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[ 37905-02-5 ] Synthesis Path-Downstream 1~35

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