DRUPACIN

Base Information

• Chemical Name: DRUPACIN
• CAS No.: 12772-83-7
• Molecular Formula: C14H16 O3
• Molecular Weight: 232.27
• Mol file: 12772-83-7.mol

Synonyms:2-Propenoicacid, 3-(3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-yl)-, (E)-; Drupacin; Dupracine

Chemical Property of DRUPACIN

Chemical Property:

• PSA: 46.53000
• LogP: 2.88800

Purity/Quality:

Dupracine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dupracine, is a new component of Psoralea drupaceae. It can be used in the synthesis of a series of 2,2-Dimethylchroman-6-ylalkanoic Acids, possessing potential antisickling properties. It is also shown to have growth-inhibitory activities toward Tenebrio molitor.

Technology Process of DRUPACIN

There total 7 articles about DRUPACIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde (61370-75-0) + malonic acid (141-82-2) → 3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid (12772-83-7)

Guidance literature:

With piperidine; In pyridine; for 6h; Heating;

DOI:10.1016/S0968-0896(99)00273-4

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid (12772-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphoric acid / Petroleum ether / 24 h / 20 °C

2: piperidine / 2 h / 80 °C

With piperidine; phosphoric acid; In Petroleum ether;

DOI:10.1039/d0nj02125c

Reference yield:

isoprene (78-79-5,9003-31-0) → 3-[2,2-dimethyl-3,4-dihydro-(2H)-benzopyran-6-yl]-2E-propenoic acid (12772-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphoric acid / Petroleum ether / 24 h / 20 °C

2: piperidine / 2 h / 80 °C

With piperidine; phosphoric acid; In Petroleum ether;

DOI:10.1039/d0nj02125c

upstream raw materials:

3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde

malonic acid

4-hydroxy-benzaldehyde

isoprene

Downstream raw materials:

(E)-3-(2,2-dimethylchroman-6-yl)-N-(3-fluoro-4-(methylsulfonamido)benzyl)acrylamide

Refernces

• 1、 Li, Fu-Nan,Kim, Nam-Jung,Paek, Seung-Mann,Kwon, Do-Yeon,Min, Kyung Hoon,Jeong, Yeon-Su,Kim, Sun-Young,Park, Young-Ho,Kim, Hee-Doo,Park, Hyeung-Geun,Suh, Young-Ger. "Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists". experimental part. p. 3557 - 3567. Retrieved 2009/09/27.
• 2、 Fatope,Abraham. "Design, synthesis, and testing of potential antisickling agents. 10. (2,2-Dimethylchroman-6-yl)alkanoic acids". . p. 1973 - 1977. Retrieved 2007/10/02.