18529-47-0

Basic information

• Product Name: 6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxy-2H-1-benzopyran-2-one
• Synonyms: 6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxy-2H-1-benzopyran-2-one;6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxycoumarin;Suberenol;trans-Suberenol
• CAS NO: 18529-47-0
• Molecular Formula: C15H16O4
• Molecular Weight: 0
• Mol File: 18529-47-0.mol

Chemical Properties

• Boiling Point: 466.9°C at 760 mmHg
• Flash Point: 176.7°C
• Appearance: /
• Density: 1.224g/cm³
• Vapor Pressure: 1.62E-09mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxy-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxy-2H-1-benzopyran-2-one(18529-47-0)
• EPA Substance Registry System: 6-[(E)-3-Hydroxy-3-methyl-1-butenyl]-7-methoxy-2H-1-benzopyran-2-one(18529-47-0)

Safety Data

• Hazardous Substances Data: 18529-47-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H16O4/c1-15(2,17)7-6-11-8-10-4-5-14(16)19-13(10)9-12(11)18-3/h4-9,17H,1-3H3/b7-6+

Upstream product

• 54102-23-7 6-bromo-7-methoxycoumarin 
• 115-18-4 2-methyl-3-buten-2-ol 
• 581-31-7 suberosin 
• 54102-22-6 6-bromoumbelliferone 
• 6626-15-9 4-Bromoresorcinol 
• 115152-07-3 6-Iodo-7-methoxy-2H-chromen-2-one 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 114032-19-8 6-(3-hydroxy-3-methylbut-1-yn-1-yl)-7-methoxy-2H-chromen-2-one 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 531-59-9 7-methoxycoumarin 

Downstream Products

• 129722-89-0 acrimarine-F 

Relevant articles and documents

Synthesis of Acrimarins from 1,3,5-Trioxygenated-9-acridone Derivatives

1,3,5-Trihydroxy-9(10H)-acridinone (1) was prepared from 3-hydroxyanthranillic acid with phloroglucinol. 1,3-Dihydroxy-5-methoxy-9(10H)-acridinone (2) was prepared from 3-methoxyanthranillic acid and phloroglucinol. Methylation of 1 under different conditions gave 1-hydroxy-3,5-dimethoxy (3), 1-hydroxy-3,5-dimethoxy-10-methyl (4), 1-hydroxy-3,5-dimethoxy-4-methyl (5), 1,3,5-trimethoxy-10-methyl (6) and 1,3,5-trimethoxy-4,10-dimethyl (7) analogues. Demethylation of 4 afforded the 1,3,5-trihydroxy-10-methyl analogue 8. Condensation of acridones 1, 2, 3 and 4 individually with E-suberenol (9) gave four novel acrimarins (acridone-coumarin dimers) 10, 11, 12 and 13 respectively, while the acridone 8 gave previously reported acrimarin-G (14).

Half-Sandwich Ruthenium Carbene Complexes Link trans-Hydrogenation and gem-Hydrogenation of Internal Alkynes

The hydrogenation of internal alkynes with [Cp?Ru]-based catalysts is distinguished by an unorthodox stereochemical course in that E-alkenes are formed by trans-delivery of the two H atoms of H2. A combined experimental and computational study now provides a comprehensive mechanistic picture: a metallacyclopropene (??2-vinyl complex) is primarily formed, which either evolves into the E-alkene via a concerted process or reacts to give a half-sandwich ruthenium carbene; in this case, one of the C atoms of the starting alkyne is converted into a methylene group. This transformation represents a formal gem-hydrogenation of a ?€-bond, which has hardly any precedent. The barriers for trans-hydrogenation and gem-hydrogenation are similar: whereas DFT predicts a preference for trans-hydrogenation, CCSD(T) finds gem-hydrogenation slightly more facile. The carbene, once formed, will bind a second H2 molecule and evolve to the desired E-alkene, a positional alkene isomer or the corresponding alkane; this associative pathway explains why double bond isomerization and over-reduction compete with trans-hydrogenation. The computed scenario concurs with para-hydrogen-induced polarization transfer (PHIP) NMR data, which confirm direct trans-delivery of H2, the formation of carbene intermediates by gem-hydrogenation, and their evolution into product and side products alike. Propargylic aOR (R = H, Me) groups exert a strong directing and stabilizing effect, such that several carbene intermediates could be isolated and characterized by X-ray diffraction. The gathered information spurred significant preparative advances: specifically, highly selective trans-hydrogenations of propargylic alcohols are reported, which are compatible with many other reducible functional groups. Moreover, the ability to generate metal carbenes by gem-hydrogenation paved the way for noncanonical hydrogenative cyclopropanations, ring expansions, and cycloadditions.

Spectrometric Elucidation of Acrimarines, the First Naturally Occuring Acridone-Coumarin Dimers

The structures of acrimarine-A (1), -B (2), -C (3), -D (4), -E (5), -F (6), and -G (7), novel acridone alkaloids carrying a coumarin unit, from the root of Citrus funadoko have been elucidated by spectrometric studies using 1H-13C long-range COSY experiments; acrimarine-A (1) and -F (6) have also been synthesized from the corresponding acridones and coumarins.

Synthesis of the Natural Coumarins (E)-Suberenol, Cyclobissuberodiene and Two Other Related New Coumarins

The total synthesis of (E)-Suberenol (1) was carried out under the conditions of palladium-catalysed Heck condensation.Two other new coumarins, (E)-7-methoxy-6-(3-methyl-1,3-butadienyl)coumarin (3) and (E)-7-methoxy-6-(3-methyl-1-butenyl)coumarin (4) and cyclobisuberodiene (2) were synthesised from (E)-suberenol.