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77-23-6

Basic Information
CAS No.: 77-23-6
Name: Cyclopentanecarboxylicacid, 1-phenyl-,2-[2-(diethylamino)ethoxy]ethyl ester
Molecular Structure:
Molecular Structure of 77-23-6 (Cyclopentanecarboxylicacid, 1-phenyl-,2-[2-(diethylamino)ethoxy]ethyl ester)
Formula: C20H31NO3
Molecular Weight: 333.46
Synonyms: 1-Phenylcyclopentane-1-carboxylicacid diethylaminoethoxyethyl ester;2-(2-Diethylaminoethoxy)ethyl1-phenylcyclopentanecarboxylate;2-(Diethylaminoethoxy)ethyl1-phenyl-1-cyclopentanecarboxylate;Atussil;Carbetapentane;Pentoxiverine;
EINECS: 201-014-1
Density: 1.048 g/cm3
Melting Point:
Boiling Point: 435.5 °C at 760 mmHg
Flash Point: 217.2 °C
Solubility:
Appearance:
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 38.77000
LogP: 3.40000
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Specification

The CAS registry number of Cyclopentanecarboxylic acid,1-phenyl-,2-[2-(diethylamino)ethoxy]ethyl ester is 77-23-6. Its EINECS registry number is 201-014-1. The IUPAC name is 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate. In addition, the molecular formula is C20H31NO3 and the molecular weight is 333.47. It belongs to the class of Miscellaneous Biochemicals.

Physical properties about this chemical are: (1)ACD/LogP: 3.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.22; (4)ACD/LogD (pH 7.4): 1.06; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.1; (7)ACD/KOC (pH 5.5): 1.26; (8)ACD/KOC (pH 7.4): 8.69; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 38.77 Å2; (13)Index of Refraction: 1.517; (14)Molar Refractivity: 96.25 cm3; (15)Molar Volume: 318.1 cm3; (16)Polarizability: 38.15×10-24cm3; (17)Surface Tension: 40.7 dyne/cm; (18)Density: 1.048 g/cm3; (19)Flash Point: 217.2 °C; (20)Enthalpy of Vaporization: 69.18 kJ/mol; (21)Boiling Point: 435.5 °C at 760 mmHg; (22)Vapour Pressure: 8.73E-08 mmHg at 25°C.

Preparation and uses of Cyclopentanecarboxylic acid,1-phenyl-,2-[2-(diethylamino)ethoxy]ethyl ester: it can be prepared by tetrahydrofuran. The reaction is as follows: (1)Add tetrahydrofuran into hydrobromic acid at first, then add sulfuric acid into the mixture. Via a series of cooling, separation and neutralization you can get 1,4-dibromobutane; (2)1,4-Dibromobutane react with cyanobenzyl to give 1-phenyl-1-cyanocyclopentane; (3)Add water and sulfuric acid into 1-phenyl-1-cyanocyclopentane. After the reaction, you can obtain 1-phenylcyclopentanecarboxylic acid; (4) Add 1-phenylcyclopentanecarboxylic acid into anhydrous trichloroethene. Then add phosphorus trichloride into the mixture with stirring. You can get 1-phenylcyclopentaneformyl chloride through this reaction; (5) 1-phenylcyclopentaneformyl chloride can react with diethylaminoethoxyethanol to give the desired product by esterification. In addition, it can be used as non-narcotic central antitussive.

You can still convert the following datas into molecular structure: 
(1)SMILES: O=C(OCCOCCN(CC)CC)C2(c1ccccc1)CCCC2
(2)InChI: InChI=1/C20H31NO3/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3
(3)InChIKey: CFJMRBQWBDQYMK-UHFFFAOYAD

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 13mg/kg (13mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacy and Pharmacology. Vol. 9, Pg. 446, 1957.
mouse LD50 oral 130mg/kg (130mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacy and Pharmacology. Vol. 9, Pg. 446, 1957.
rat LD50 oral 150mg/kg (150mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacy and Pharmacology. Vol. 9, Pg. 446, 1957.