32846-66-5|Pentacyclo[4.2.0.02,5.03,8.04,7]octane-1,4-dicarboxylic acid| Ambeed

CAS No. :	32846-66-5
Formula :	C₁₀H₈O₄
M.W :	192.17
SMILES Code :	O=C(C12C3C4C5(C(O)=O)C3C1C5C24)O
MDL No. :	MFCD08458496
InChI Key :	JFKXMJUMOJJTCQ-UHFFFAOYSA-N
Pubchem ID :	276350

Safety of [ 32846-66-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 32846-66-5 ]

* 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 [ 32846-66-5 ]

[ 32846-66-5 ] Synthesis Path-Downstream 1~54

1
[ 67-56-1 ]
[ 32846-66-5 ]
[ 29412-62-2 ]

References: [1]Organic Process Research and Development,2013,vol. 17,p. 1503 - 1509.
[2]Journal of the American Chemical Society,1976,vol. 98,p. 3075 - 3085.
[3]Russian Chemical Bulletin,1993,vol. 42,p. 770 - 771.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 801 - 802.
[4]Australian Journal of Chemistry,1997,vol. 50,p. 189 - 192.
[5]Synthesis,2010,p. 98 - 102.
[6]Thermochimica Acta,2010,vol. 499,p. 15 - 20.
[7]Organic Letters,2017,vol. 19,p. 2698 - 2701.

2
[ 53510-13-7 ]
[ 32846-66-5 ]
bis(2-fluoro-2,2-dinitroethyl) pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1,4-dicarboxylate [ No CAS ]

References: [1]Russian Chemical Bulletin,1993,vol. 42,p. 770 - 771.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 801 - 802.

3
[ 918-54-7 ]
[ 32846-66-5 ]
bis(2,2,2-trinitroethyl) pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>-octane-1,4-dicarboxylate [ No CAS ]

References: [1]Russian Chemical Bulletin,1993,vol. 42,p. 770 - 771.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 801 - 802.

4
[ 29412-62-2 ]
[ 32846-66-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 14h;Inert atmosphere;	A 2.5 M solution of NaOH in MeOH (7.60 mL, 19.1 mmol, 1.05 equiv.) was added dropwise to a solution of 27 (4.00 g, 18.2 mmol) in THF (125 mL) at rt. The mixture was stirred for 14 h and the solvent evaporated in vacuo without heating. The residue was diluted with H2O (45 mL) and extracted with CHCl3 (3 × 15 mL). The aqueous layer was acidified to pH 3 with 32% aq. HCl, extracted with CHCl3 (1 × 60 mL, 2 × 35 mL), and the combined organic layers dried (MgSO4). The solvent was evaporated under reduced pressure to give 28 as a colourless crystalline solid (3.46 g, 92%) with spectroscopic properties matching those previously reported:3 m.p. 183-184.5 C; (lit. m.p.3 182-183 C); 1H NMR (200.1 MHz, CDCl3); delta 4.30-4.24 (6H, m, CH), 3.72 (3H, s, CH3).
70%		Cubane-1 ,4-dicarboxylic acid dimethyl esther(Pharmatech International Inc.) (3.10 g, 14.1 mmol) is dissolved in 15 ml of hot methanol in a 250 ml in a round-bottomed flask equipped with a condenser. Solid reagent NaOH (0.560 g, 14.1 mmol) is added, and the reaction mixture is heated under refluxed for a 13-15 hr period. The reaction mixture is then cooled to room temperature. The reaction mixture is diluted with 120 ml of water and extracted 3 times with 50 ml portions of ether, which is discarded.. The aqueous portion is acidified to ca. pH 3 with 6N HCl and then extracted with chloroform (4 portions of ca. 50 ml each). The combined chloroform extracts are dried and reduced by rotary evaporation to produce the diacid as an off-white powder in 70% yield.
	With water; sodium hydroxide;	Dimethyl cubane-1,4-dicarboxylate (3a) was prepared according to a known literature method.25 The diester was converted to the diacid upon treatment with NaOH/H2O, then precipitated with HCl/H2O, and washed thoroughly with distdwater. The diacid was recrystallized twice from glacial acetic acid, and was dried in vacuo prior to use. Compound 6 is a white powder. deltaH (250MHz, DMSO-d6): 4.10 (s, 6H). deltaC (62.5MHz, DMSO-d6): 172.7 (2C, carbonyl), 55.8 (2C, quaternary), 46.3 (6C, CH).

References: [1]Synthesis,1995,p. 501 - 502.
[2]Thermochimica Acta,2010,vol. 499,p. 15 - 20.
[3]Journal of Organic Chemistry,1989,vol. 54,p. 5783 - 5788.
[4]Organic Letters,2014,vol. 16,p. 4094 - 4097.
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4059 - 4063.
[6]Organic and Biomolecular Chemistry,2019,vol. 17,p. 1067 - 1070.
[7]Patent: WO2007/59330,2007,A2 .Location in patent: Page/Page column 40.
[8]Chemistry - A European Journal,2019,vol. 25,p. 8344 - 8352.
[9]Journal of Organic Chemistry,1991,vol. 56,p. 5138 - 5142.
[10]Journal of Physical Chemistry,1996,vol. 100,p. 9598 - 9604.
[11]Tetrahedron,2013,vol. 69,p. 5160 - 5163.
[12]ACS Chemical Neuroscience,2014,vol. 5,p. 335 - 339.
[13]Journal of Physical Chemistry A,2016,vol. 120,p. 4418 - 4428.

5
[ 25867-85-0 ]
[ 32846-66-5 ]
C₁₀H₈O₄ [ No CAS ]

References: [1]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 2676 - 2681.

6
[ 32846-66-5 ]
[ 59346-70-2 ]

References: [1]Canadian Journal of Chemistry,1992,vol. 70,p. 910 - 914.
[2]Journal of the American Chemical Society,1976,vol. 98,p. 3075 - 3085.
[3]Journal of Physical Chemistry,1996,vol. 100,p. 9598 - 9604.

7
[ 32846-66-5 ]
[ 60462-24-0 ]

References: [1]Journal of the American Chemical Society,1976,vol. 98,p. 3075 - 3085.
[2]Tetrahedron Letters,1989,vol. 30,p. 6967 - 6968.
[3]Journal of Organic Chemistry,1991,vol. 56,p. 1305 - 1307.
[4]Journal of Organic Chemistry,1988,vol. 53,p. 5353 - 5355.
[5]Synthesis,1995,p. 501 - 502.
[6]Journal of Organic Chemistry,1995,vol. 60,p. 966 - 968.
[7]Liebigs Annales,1996,p. 311 - 315.
[8]Russian Chemical Bulletin,1998,vol. 47,p. 441 - 446.
[9]Journal of Physical Chemistry A,2016,vol. 120,p. 4418 - 4428.
[10]Organic and Biomolecular Chemistry,2019,vol. 17,p. 1067 - 1070.
[11]Journal of the American Chemical Society,2019.

8
[ 32846-66-5 ]
[ 129380-05-8 ]
[ 129380-06-9 ]
[ 97229-08-8 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 805 - 806.

9
[ 32846-66-5 ]
[ 129380-05-8 ]
[ 97229-08-8 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 805 - 806.
[2]Tetrahedron Letters,1990,vol. 31,p. 805 - 806.

10
[ 32846-66-5 ]
[ 97229-08-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; In 1,2-dichloro-ethane; for 2h;Reflux; Irradiation;Product distribution / selectivity;	EXAMPLE 3; Radical iodo-de-caboxylation induced by TV-iodo amides/V-iodo amideR-COOH - R-lGeneral procedure[00111] Procedure: A mixture of R-COOH (1 mmol), N-iodo amide (1-4 equiv), and solvent (3-6 mL) was refluxed (Delta) for 1-24 h in the dark (NL) or under irradiation with 500 W tungsten lamp (TL) or under fluorescent room lighting (FL).[00112] Treatment: The reaction mixture was cooled to rt, and washed with aq NaHS03 and NaHC03 to destroy excess of iodination agent and dissolve unreacted carboxylic acid. The organic solution was dried (Na2S04), filtered through short silica or alumina pad and concentrated in vacuo to give iodide R-I. 100113J Purification: Optionally, the iodide R-I was further purified by crystallization (if the iodide is crystalline compound), or rectification (if the iodide is liquid compound). Analytical sample of the product was purified by column chromatography./V-iodoamideAlk-COOH - Alk-I[00114] A mixture of Alk-COOH (1 mmol), N-iodo amide (1-3 equiv), and solvent (4 mL) was refluxed (Delta) in the dark (NL) or under irradiation with 500 W tungsten lamp (TL), or under fluorescent room lighting (FL).

References: [1]Patent: WO2011/154953,2011,A1 .Location in patent: Page/Page column 28-30.
[2]Journal of the American Chemical Society,1999,vol. 121,p. 4111 - 4123.
[3]Thermochimica Acta,2010,vol. 499,p. 15 - 20.
[4]Journal of Organic Chemistry,1989,vol. 54,p. 722 - 723.
[5]Organic Letters,2014,vol. 16,p. 4094 - 4097.
[6]Canadian Journal of Chemistry,1992,vol. 70,p. 910 - 914.

11
[ 32846-66-5 ]
C₁₀H₉BrO₄ [ No CAS ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2823 - 2826.

12
[ 32846-66-5 ]
[ 125848-35-3 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 2823 - 2826.

13
[ 32846-66-5 ]
[ 67-63-0 ]
di-iso-propyl pentacyclo<4.2.0.0^2,5.0^3,8.0^4,7>octane-1,4-dicarboxylate [ No CAS ]

References: [1]Russian Chemical Bulletin,1993,vol. 42,p. 770 - 771.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1993,p. 801 - 802.

14
[ 32846-66-5 ]
[ 75-65-0 ]
[ 87830-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; triethylamine; for 16h;Reflux;	Example 4A: cubane-1, 4-diamine dihydrochloride A 50 mL round bottom flask, equipped with a magnetic stir bar, was charged with cubane-l,4-dicarboxylic acid (Aldrich, CASNo. 32846-66-5, 800 mg, 4.16 mmol), triethylamine (1.16 mL, 8.32 mmol), diphenylphosphoryl azide (1.8 mL, 8.35 mmol), and /-butanol (12.8 mL). The flask was fitted with a reflux condenser equipped with a calcium sulfate drying tube, and the reaction mixture was stirred at reflux for 16 hours. The reaction mixture was allowed to cool to ambient temperature, and then poured into saturated aqueous sodium bicarbonate (50 niL). The precipitate was collected by filtration and washed with water. The solid was dissolved in a hot mixture of dichloromethane, tetrahydrofuran, ethyl acetate, and ethanol. This warm solution was dried (MgSC) and filtered. The filtrate was concentrated under reduced pressure to give a beige solid that was treated with ether and collected by filtration. The crude, bis-(Yer/-butoxy-carbonyl)-protected intermediate was suspended in methanol (30 mL) and treated with 4 M HC1 in dioxane (30 mL, 120 mmol, 47.4 equivalents). The reaction mixture was stirred at ambient temperature for 4 hours. Volatiles were removed under reduced pressure to give a pale brown solid that was washed with diethyl ether and then with ethyl acetate. The solid was dissolved in hot methanol and treated with acetone to induce precipitation. The title intermediate solid was collected by filtration (125 mg, 14.5% yield). XH NMR (methanol-^) 5 Dppm 4.23 (s, 6H). MS (DCI-NH3) m/z 135 (M+H)+, m/z 152 (M+NH4)+, m/z 169 (M+NH4+NH3)+.

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 185 - 186.
[2]Journal of Organic Chemistry,1989,vol. 54,p. 5783 - 5788.
[3]Patent: WO2017/193034,2017,A1 .Location in patent: Page/Page column 224-225.

15
[ 32846-66-5 ]
[ 60462-27-3 ]

References: [1]Russian Chemical Bulletin,1998,vol. 47,p. 1349 - 1352.
[2]Journal of the American Chemical Society,1976,vol. 98,p. 3075 - 3085.
[3]Organic Letters,2017,vol. 19,p. 2698 - 2701.

16
[ 25867-88-3 ]
[ 32846-66-5 ]

References: [1]Journal of the American Chemical Society,1976,vol. 98,p. 3075 - 3085.

17
[ 29412-62-2 ]
[ 24539-28-4 ]
[ 32846-66-5 ]

References: [1]Synthesis,1995,p. 501 - 502.
[2]Australian Journal of Chemistry,1986,vol. 39,p. 2061 - 2066.

18
[ 60462-18-2 ]
[ 53578-15-7 ]
[ 32846-66-5 ]

References: [1]Australian Journal of Chemistry,1986,vol. 39,p. 2061 - 2066.

19
[ 25867-85-0 ]
[ 32846-66-5 ]

References: [1]Australian Journal of Chemistry,1997,vol. 50,p. 189 - 192.

20
[ 100-02-7 ]
[ 32846-66-5 ]
1,4-Bis(4-nitrophenoxycarbonyl)cubane [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 463 - 469.

22
[ 32846-66-5 ]
SOCl₂ [ No CAS ]
[ 60462-24-0 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 5138 - 5142.

23
[ 32846-66-5 ]
4,4'-dimethylbicubyl [ No CAS ]