161753-49-7

Basic information

• Product Name: 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-
• Synonyms: 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, trans-;(?à)-12-Oxocalanolide A;12-Oxocalanolide A;151005-67-3
• CAS NO: 161753-49-7
• Molecular Formula: C22H24 O5
• Molecular Weight: 368.42
• Mol File: 161753-49-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 546.7°Cat760mmHg
• Flash Point: 298.4°C
• Appearance: /
• Density: 1.176g/cm³
• CAS DataBase Reference: 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-(161753-49-7)
• EPA Substance Registry System: 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-(161753-49-7)

Safety Data

• Hazardous Substances Data: 161753-49-7(Hazardous Substances Data)

Usage

General Description

The chemical compound "2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione, 10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel-" is a complex organic molecule with multiple rings and functional groups. It is a derivative of benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione, with substitutions at the 10th and 11th positions. The 10R,11R configuration indicates the stereochemistry of the molecule. The dihydro-6,6,10,11-tetramethyl-4-propyl substitution adds four methyl groups and a propyl group to the structure. 2H,6H,12H-Benzo[1,2-b:3,4-b':5,6-b'']tripyran-2,12-dione,10,11-dihydro-6,6,10,11-tetramethyl-4-propyl-, (10R,11R)-rel- likely has unique chemical and biological properties due to its specific structure and functional groups.

Upstream product

• 263351-94-6 (10R,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 
• 108-73-6 3,5-dihydroxyphenol 
• 166983-61-5 HI-D₁₂ 
• 334881-61-7 (8R,9S)-8,9-dihydro-8,9-dimethyl-5-methoxy-4-propyl-2H,10H-benzo[1,2-b;5,6-b']dipyran-2,10-dione 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 685844-44-4 5-hydroxy-8,9-dimethyl-4-propyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione 
• 185339-28-0 5-Hydroxy-6-((2R,3R)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 
• 185339-26-8 5-Hydroxy-6-((2R,3S)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 
• 172805-19-5 5-Hydroxy-2,2-dimethyl-6-<(E)-2-methylbut-2-enoyl>-10-propyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one 
• 50-00-0 formaldehyd 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 185824-43-5 (cis,trans)-2,3-dihydro-2,3-dimethyl-9-hydroxy-8-propyl-4H,6H-benzo<1,2-b:3,4-b>dipyran-4,6-dione 
• 738600-86-7 C₂₂H₂₆O₆ 
• 105-57-7 diethyl acetal 

Downstream Products

• 183904-55-4 HI-D₈₆ 
• 183904-54-3 (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 
• 909-13-7 7,8-dihydro-(-)-calanolide B 
• 142632-32-4 (+)-calanolide A 
• 142632-33-5 (+)-calanolide B 

Relevant articles and documents

Total synthesis of (±)-Calanolide A

The total synthesis of (±)-Calanolide A, incorporating a ring-forming sequence different from previous procedures, is described.

Novel Approach for Synthesis of (+/-)-Calanolide A and Its Anti-HIV Activity

Anti-HIV agent (+/-)-calanolide A (1) has been synthesized.The key intermediate, chromone 5, was synthesized by the sequence of Pechmann reaction, acylation and chromenylation by 4,4-dimethoxy-2-methylbutan-2-ol.The anti-HIV activity for synthetic (+/-)-1 has been determined and compared with the natural product.

Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B

The Δ7,8 olefinic linkages within (+)-calanolide A (1) and (-)- calanolide B (2) were catalytically reduced to determine impact on the anti- HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.

Preparation of a trans-calanolide ketone intermediate and chiral separation of calanolide alcohols to give racemic calanolide A

The method of the invention comprises a process for synthesizing a trans-calanolide A ketone intermediate used in the synthesis of racemic trans-calanolide A. The invention further comprises a method for removing a racemic calanolide B diastereomer from a

Methods for preparing antiviral calanolide compounds

The present invention relates to methods for preparing 2,2-dimethyl-5-acyloxy-10-propyl-2H,8H-benzo[ 1,2-b:3,4-b ′]dipyran-8-one (5) and 2,2-dimethyl-5-hydroxy- 10-propyl-2H,8H-benzo[1,2-b:3,4-b ′]dipyran-8-one (6) and their use as intermediates for the synthesis of antiviral calanolide compounds. For example, Fries rearrangement on compound 5 or Friedel-Crafts reaction on 6, yields intermediate 2,2-dimethyl-5-hydroxy-6-propionyl-10-propyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-8-one (4), which, in turn, can be converted to (+)-calanolide A and (?)-calanolide B. The coupling of compound 6 with the appropriate chiral molecule under Mitsunobu or nucleophilic displacement leads to the asymmetric synthesis of antiviral calanolide compounds.