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4017-56-5

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4017-56-5 Usage

Chemical Properties

clear colorless liquid

Uses

Ethyl 2-oxo-1-cyclooctanecarboxylate (2-carbethoxycyclooctanone) may be used in the synthesis of 2-carbethoxy-2-cyclooctenone.

General Description

Ethyl 2-oxo-1-cyclooctanecarboxylate (2-carbethoxycyclooctanone) is a β-keto ester. It undergoes Michael addition with 3-buten-2-one (methyl vinyl ketone, MVK) in the presence of potassium bis(1,2-benzenediolato)phenylsilicate to afford the corresponding 1,4-adduct. It can be synthesized from cycloheptanone. Its boiling point, density and refractive index have been determined.

Check Digit Verification of cas no

The CAS Registry Mumber 4017-56-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,1 and 7 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4017-56:
(6*4)+(5*0)+(4*1)+(3*7)+(2*5)+(1*6)=65
65 % 10 = 5
So 4017-56-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H18O3/c1-2-14-11(13)9-7-5-3-4-6-8-10(9)12/h9H,2-8H2,1H3/t9-/m1/s1

4017-56-5Relevant articles and documents

Activated cyclooctenones are effective dienophiles

Liu,Wang,Kim,Browne,Wang

, p. 899 - 912 (1997)

The first Diels-Alder addition of a diene to a cyclooctenone dienophile has been observed. Three activated cyclooctenone dienophiles 1,2, and 3 are studied with a variety of simple and functionalized dienes. Diels-Alder adducts are produced in excellent yields under very mild Lewis acid catalyzed conditions. The usual orientation rules are followed and, as predicted, the products are formed for the most part exclusively by ester-endo addition. The stereoselectivity is influenced by the substitution pattern of the diene in some cases. The factors influencing the stereochemical selectivity of the addition are discussed in some detail.

A new series of cycloalkane-fused coumarin sulfonates: Synthesis and in vitro antiproliferative screening

El-Gamal, Mohammed I.,Baek, Daejin,Oh, Chang-Hyun

, p. 184 - 191 (2016/02/26)

In this paper, we report the synthesis of 14 new cycloalkane-fused tricyclic coumarin sulfonate derivatives. They were examined for in vitro anticancer activity against NCI-57 cancer cell line panel of nine different cancer types. Among all the target analogs, compounds 1c, 1e, and 1n showed the highest activities. Compound 1e exerted the highest percentage growth inhibition (91.91%) against SNB-75 CNS cancer cell line at 10 μM concentration and was more active than carmustineagainst this cell line. Compound 1c also showed strong activity against HT29 colon, ACHN renal, and PC-3 prostate cancer cell lines. Furthermore, compound 1n was selective toward the HT29 colon cancer cell line. Compounds 1c, 1e, and 1n showed superior selectivity against cancer cell lines compared to the noncancerous RAW 264.7 macrophages. The in silico predictions estimate the oral bioavailability, which is in compliance with Lipinski's rule of five.

Synthesis of tricyclic fused coumarin sulfonates and their inhibitory effects on LPS-induced nitric oxide and PGE2 productions in RAW 264.7 macrophages

Jang, Hyeon-Lok,El-Gamal, Mohammed I.,Choi, Hye-Eun,Choi, Ho-Yeong,Lee, Kyung-Tae,Oh, Chang-Hyun

, p. 571 - 575 (2014/01/23)

The regulations of NO and PGE2 productions are research topics of interest in the field of antiinflammatory drug development. In the present study, a series of tricyclic fused coumarin sulfonate derivatives was synthesized and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 macrophages. Among all the target compounds, compound 1g possessing p-(trifluoromethyl)phenyl and fused cycloheptane moieties showed the highest inhibitory effects on NO and PGE 2 productions. Compound 1g not only inhibited COX-2 activity but also reduced expressions of COX-2 and iNOS. Furthermore, ADME profiling showed that compounds 1g, 1j, 1m, and 1n are estimated to be orally bioavailable.

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