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CAS No.: | 5442-12-6 |
---|---|
Name: | Norcantharidin |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C8H8O4 |
Molecular Weight: | 168.149 |
Synonyms: | 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylicanhydride (8CI);4,10-Dioxatricyclo[5.2.1.02,6]decane-3,5-dione;NSC 14003;4,7-Epoxyisobenzofuran-1,3-dione,hexahydro-; |
EINECS: | 637-280-4 |
Density: | 1.468 g/cm3 |
Melting Point: | 110 °C |
Boiling Point: | 362.464 °C at 760 mmHg |
Flash Point: | 167.017 °C |
Appearance: | solid |
PSA: | 52.60000 |
LogP: | -0.13660 |
endo-7-oxabicyclo<2.2.1>heptane-2,3-dicarboxylic acid
endothall anhydride
Conditions | Yield |
---|---|
In acetyl chloride | 99% |
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In ethyl acetate for 16h; Heating / reflux; | 98% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 24h; | 97% |
With hydrogen In ethyl acetate at 280℃; | 81% |
methanol
endothall anhydride
3-(methoxycarbonyl)-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid
Conditions | Yield |
---|---|
at 60℃; for 16h; | 98% |
for 3h; Heating / reflux; | 96% |
at 80 - 85℃; for 3.5h; | 72.2% |
at 80 - 85℃; for 15.5h; Cooling; | 24.2% |
endothall anhydride
ethanol
7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid monoethyl ester
Conditions | Yield |
---|---|
at 80℃; for 4.5h; | 87% |
at 80℃; for 4.5h; | 87% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
In toluene for 2h; Heating / reflux; | 74% |
endothall anhydride
benzyl alcohol
7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid, mono (phenylmethyl)ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 160℃; for 6h; | 71.2% |
endothall anhydride
1-t-Butoxycarbonylpiperazine
4-(3-carboxy-7-oxa-bicyclo[2.2.1]heptane-2-carbonyl)piperazine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
In toluene at 100 - 110℃; for 8h; | 47% |
In toluene at 100℃; for 8h; |
Conditions | Yield |
---|---|
With zeolite Y with a silica-alumina at 200℃; Inert atmosphere; | A 41% B 23% |
endothall anhydride
4-amino-1-(2-(4-methoxyphenyl)ethyl)piperidine
3-{1-[2-(4-methoxy-phenyl)-ethyl]piperidin-4-ylcarbamoyl}-7-oxa-bicyclo[2.2.1]-heptane-2-carboxylic acid
Conditions | Yield |
---|---|
In toluene at 100℃; for 20h; | 36% |
The Norcantharidin, with the CAS registry number 5442-12-6, is also known as 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride. It belongs to the product categories of Norbornene Derivatives; Plant extract. This chemical's molecular formula is C8H8O4 and molecular weight is 168.15. What's more, its systematic name is 4,10-Dioxatricyclo[5.2.1.02,6]decane-3,5-dione. It is used as antineoplastic agents.
Physical properties of Norcantharidin are: (1)ACD/LogP: -0.971; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.97; (4)ACD/LogD (pH 7.4): -0.97; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 7.06; (8)ACD/KOC (pH 7.4): 7.06; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 52.6 Å2; (13)Index of Refraction: 1.55; (14)Molar Refractivity: 36.47 cm3; (15)Molar Volume: 114.53 cm3; (16)Polarizability: 14.458×10-24cm3; (17)Surface Tension: 50.12 dyne/cm; (18)Density: 1.468 g/cm3; (19)Flash Point: 167.017 °C; (20)Enthalpy of Vaporization: 60.841 kJ/mol; (21)Boiling Point: 362.464 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: C1CC2C3C(C1O2)C(=O)OC3=O
(2)Std. InChI: InChI=1S/C8H8O4/c9-7-5-3-1-2-4(11-3)6(5)8(10)12-7/h3-6H,1-2H2
(3)Std. InChIKey: JAABVEXCGCXWRR-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 10mg/kg (10mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#05066. |