19250-17-0|6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylic acid| Ambeed

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Quality Control of [ 19250-17-0 ] Purity: 95% SDS Specification

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Product Details of [ 19250-17-0 ]

CAS No. :	19250-17-0
Formula :	C₁₀H₁₄O₂
M.W :	166.22
SMILES Code :	O=C(C1=CCC2C(C)(C)C1C2)O
MDL No. :	MFCD20620912
InChI Key :	XPHVDOXZJRTIMV-UHFFFAOYSA-N
Pubchem ID :	86840

Safety of [ 19250-17-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 19250-17-0 ]

* 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 [ 19250-17-0 ]

[ 19250-17-0 ] Synthesis Path-Downstream 1~26

1
[ 19250-17-0 ]
6,6-dimethylbicyclo[3.1.1]heptane-2-carboxylic acid [ No CAS ]

References: [1]Chemische Berichte,1907,vol. 40,p. 1369.

2
[ 515-00-4 ]
[ 19250-17-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1965,vol. 38,p. 1503 - 1505.

3
[ 515-00-4 ]
[ 19250-17-0 ]
[ 564-94-3 ]

References: [1]Russian Chemical Bulletin,1996,vol. 45,p. 1781 - 1782.

6
myrtenal oxime [ No CAS ]
[ 19250-17-0 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 1369.

7
[ 71-41-0 ]
[ 19250-17-0 ]
sodium [ No CAS ]
6,6-dimethylbicyclo[3.1.1]heptane-2-carboxylic acid [ No CAS ]

References: [1]Chemische Berichte,1907,vol. 40,p. 1369.

8
[ 177698-18-9 ]
[ 19250-17-0 ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.
[2]Patent: CN113121426,2021,A .
[3]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12956 - 12965.

9
[ 564-94-3 ]
[ 19250-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile; at 10℃; for 7h;	A solution of NaClO2 (8.0 g, 70 mmol) in H2O (70 mL) was added slowly in 2 h toa stirred mixture of myrtenal (GC purity 97.2%, 7.7 g, 50 mmol) in CH3CN (50 mL), NaH2PO4 (1.6 g) in water (20 mL), H2O2(35%, 5.0 mL, 52 mmol), and polyethylene glycol (PEG-400, 3.0 g) at 10C with ice-water cooling. The reaction was conductedfor 7 h. Then Na2SO3 (0.5 g) was added to destroy the unreacted HOCl and H2O2. The resulting mixture was acidified with10% aqueous HCl to pH 3 and extracted several times with diethyl ether. The separated organic phase was washed withsaturated NaHSO3 and deionized H2O, and then dried over anhydrous Na2SO4. It was then distilled in a warm bath to removethe ethyl ether, and later distilled in vacuum to give 7.0 g of myrtenic acid (3, mp 130.0-131.0C at 0.53 kPa [29], 117.0C at0.27 kPa) in 80.0% yield as a colorless transparent viscous liquid, which was kept at room temperature to afford a white waxysolid (LC purity 94.5%). UV-vis (EtOH, max, nm): 232.60. IR (KBr, , cm-1): 3500-2500 (br, O-H), 2976, 2921, 2822 (C-H),2673, 2609, 2527 (combination bands), 1682 (conjugated C=O), 1623 (C=C), 1423 ( C-O), 1273 ( C-O). 1H NMR (600 MHz,CDCl3, , ppm, J/Hz): 10.30 (1H, br, H-10), 6.98 (1H, s, H-3), 2.78 (1H, t, J = 5.6, 5.5, H-1), 2.48-2.39 (3H, m, H-4, 7), 2.13(1H, m, H-5), 1.33 (3H, s, H-9), 1.11 (1H, d, J = 9.2, H-7), 0.79 (3H, s, H-8). 13C NMR (150 MHz, CDCl3, , ppm): 171.7 (C-10),139.7 (C-2), 139.5 (C-3), 40.6 (C-5), 40.2 (C-1), 37.7 (C-6), 32.4 (C-7), 31.3 (C-4), 25.8 (C-9), 20.9 (C-8). MS (EI, 70 eV),m/z 164.82 [M - H]-.
		Dissolve 15.5g of myrylene aldehyde in 100mL of acetonitrile, and then add 5.3g of PEG-400, 40mL of 7.4% NaH2PO4 aqueous solution, 9.7mL of 30% H2O2 aqueous solution, and stir in an ice bath for 10 minutes. Cool it to below 10C, continue to stir and slowly add 100 mL of 17% NaClO2 aqueous solution dropwise. After dropping, continue to stir at room temperature for 7 hours. After the reaction, add 1.0g of sodium sulfite, and then adjust the pH of the reaction solution with an appropriate amount of dilute HCl. 3.0, then extract 3 times with anhydrous ether, 50mL each time, combine the organic phases, wash with saturated NaHSO3 and saturated brine successively, and dry the obtained organic phase with anhydrous sodium sulfate. After the ether is evaporated, the residue is depressurized Distillation, collect the 105106/6mmHg fraction to obtain a colorless viscous liquid, and let it stand for a period of time to become a waxy solid;

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.
[2]Patent: CN113121426,2021,A .Location in patent: Paragraph 0046; 0051-0052.
[3]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12956 - 12965.

10
[ 19250-17-0 ]
N-(4-(N'-pyrimidin-2-ylsulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

11
[ 19250-17-0 ]
N-(4-(N'-(4-methylpyrimidin-2-yl)sulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

12
[ 19250-17-0 ]
N-(4-(N'-(6-methoxypyridazin-3-yl)sulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

13
[ 19250-17-0 ]
N-(4-(N'-(6-chloropyridazin-3-yl)sulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

14
[ 19250-17-0 ]
myrtenoyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With thionyl chloride; N,N-dimethyl-formamide; In benzene; for 5h;Reflux;	Under an anhydrous atmosphere, a solution of SOCl2 (8.2 g, 99.0%, 68.9 mmol)in benzene (10 mL) was added slowly to a solution of <strong>[19250-17-0]myrtenic acid</strong> (LC purity 94.5%, 10.0 g, 57.4 mmol) in benzene (30 mL)at room temperature. Subsequently, three drops of DMF was added, and the mixture was refluxed for 5 h. Afterwards, thereaction solution was distilled at atmospheric pressure to remove the low-boiling components, and in vacuum to give myrtenylchloride (4, mp 76.0C at 0.27 kPa) in 75.0% yield as a faint yellow liquid (GC purity 96.9% determined in methanol). UV-vis(cyclohexane, max, nm): 250.20. IR (KBr, , cm-1): 2915, 2937, 2890 (C-H), 1747 (C=O), 1616 (C=C), 807 (C-Cl). 1H NMR(600 MHz, CDCl3, , ppm, J/Hz): 7.29 (1H, s, H-3), 2.85 (1H, m, H-1), 2.61-2.48 (3H, m, H-4, 7), 2.16 (1H, m, H-5), 1.33(3H, s, H-9), 1.11 (1H, d, J = 9.4, H-7), 0.77 (3H, s, H-8). 13C NMR (150 MHz, CDCl3, , ppm): 166.0 (C-10), 147.7 (C-2),144.5 (C-3), 42.4 (C-5), 39.9 (C-1), 37.9 (C-6), 33.0 (C-7), 31.2 (C-4), 25.6 (C-9), 20.8 (C-8).General Procedure for the Synthesis of N-(4-(N-Substituted Sulfamoyl)phenyl)myrtenamides
	With thionyl chloride; N,N-dimethyl-formamide; In benzene;Reflux;	Under absolute water conditions, dissolve 20.0g of myryl acid in 50mL of benzene, add a few drops of N,N-dimethylformamide, and slowly add a solution of 17.3g of thionyl chloride and 20mL of benzene under stirring. After the dripping, the temperature is raised and refluxed for 6-8 hours. After the reaction is completed, the benzene and unreacted thionyl chloride are removed by atmospheric distillation, and the 70-71C/5mmHg fraction is collected by vacuum distillation to obtain a pale yellow liquid.

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.
[2]Patent: CN113121426,2021,A .Location in patent: Paragraph 0046; 0053-0054.
[3]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 12956 - 12965.

15
[ 19250-17-0 ]
N-(4-sulfamoylphenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

16
[ 19250-17-0 ]
N-(4-(N'-thiazol-2-ylsulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

17
[ 19250-17-0 ]
N-(4-(N'-(5-methyl-1,3,4-thiazol-2-yl)sulfamoyl)phenyl)myrtenamide [ No CAS ]

References: [1]Chemistry of Natural Compounds,2018,vol. 54,p. 56 - 62.
Khim. Prir. Soedin.,2018,p. 52 - 57,6.

18
[ 19250-17-0 ]
C₁₆H₁₈ClN₃O₂ [ No CAS ]