5208-87-7

Usage

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes,

InChI:InChI=1/C10H10O3/c1-2-8(11)7-3-4-9-10(5-7)13-6-12-9/h2-5,8,11H,1,6H2

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 120-57-0 piperonal 
• 593-60-2 Vinyl bromide 
• 107-02-8 acrolein 
• 3536-96-7 vinylmagnesium chloride 
• 1826-67-1 vinyl magnesium bromide 
• 917-57-7 vinyllithium 
• 17581-86-1 3-(benzo[1,3]dioxol-5-yl)prop-2-en-1-ol 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 495-76-1 piperonol 

Downstream Products

• 94-62-2 Piperine 
• 59901-91-6 3-(3,4-methylenedioxyphenyl)-3-hydroxy-1,2-epoxypropane 
• 30418-53-2 1-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one 
• 872728-46-6 5-{(S)-{[(S)-3-(4-benzyloxy-3-methoxyphenyl)prop-2-enyl]oxy}[(2S)-oxiran-2-yl]methyl}-1,3-benzodioxole 
• 872728-48-8 [(2R,3S,4S)-4-(4-benzyloxy-3-methoxybenzyl)-2-(1,3-benzodioxol-5-yl)tetrahydrofuran-3-yl]methanol 
• 133-03-9 l-sesamin 
• 1375475-09-4 (S)-N-(1-(benzo[d][1,3]dioxol-5-yl)allyl)benzamide 
• 250660-51-6 2-(benzo[d][1,3]dioxol-5-yl)chromane 
• 1384560-04-6 1-(benzo[d][1,3]-dioxol-5-yl)-3-(2-bromophenyl)propan-1-ol 
• 1384560-12-6 2-(benzo[d][1,3]dioxol-5-yl)-4-(2-bromophenyl)butan-2-ol 
• 1260677-75-5 1-(1,3-benzodioxol-5-yl)-3-(2-bromophenyl)propan-1-one 
• 1384559-99-2 1-(1,3-benzodioxol-5-yl)-3-(2-bromo-5-methoxyphenyl)propan-1-one 
• 1384560-08-0 1-(1,3-benzodioxol-5-yl)-3-(2-bromo-5-methoxyphenyl)propan-1-ol 
• 1449789-82-5 3-(1,3-benzodioxol-5-yl)-5-(2-bromophenyl)pent-1-en-3-ol 

Relevant academic research and scientific papers

Metabolism of 7-ethoxycoumarin, safrole, flavanone and hydroxyflavanone by cytochrome P450 2A6 variants

CYP 2A6 is a human enzyme that metabolizes many xenobiotics including coumarin, indole, nicotine and carcinogenic nitrosamines. The gene for CYP2A6 is polymorphic. There are few data available to clarify the relationship between P450 genetic variants and the metabolism of materials in food. The CYP 2A6 wild-type protein and 13 mutants (CYP2A6.1, CYP2A6.2, CYP2A6.5, CYP2A6.6, CYP2A6.7, CYP2A6.8, CYP2A6.11, CYP2A6.15, CYP2A6.16, CYP2A6.17, CYP2A6.18, CYP2A6.21, CYP2A6.23 and CYP2A6.25) were co-expressed with NADPH-cytochrome P450 reductase in E. coli. The hydroxylase activities toward 7-ethoxycoumarin, coumarin, safrole, flavanone and hydroxyflavanone were examined. Ten types of CYP2A6 variants except for CYP2A6.2, CYP2A6.5 and CYP2A6.6 showed Soret peaks (450 nm) typical of P450 in the reduced CO-difference spectra and had 7-ethoxycoumarin O-deethylase activities. CYP2A6.15 and CYP2A6.18 showed higher activities for safrole 1′-hydroxylation than CYP2A6.1. CYP2A6.25 and CYP2A6.7 had lower safrole 1′-hydroxylase activities. CYP2A6.7 had lower flavanone 6- and 2′-hydroxylase activities, whereas CYP2A6.25 had higher 6-hydroxylase activity and lower 2′-hydroxylase activity. Hydroxyflavanone was metabolized by CYP2A6.25, but was not metabolized by wild-type CYP2A6.1. These results indicate that CYP2A6.25 possessed new substrate specificity toward flavonoids. Copyright 2012 John Wiley & Sons, Ltd. Copyright

Iridium-Catalyzed Asymmetric Allylic Alkylation of Deconjugated Butyrolactams

Compared with the ever-growing list of nonprochiral nucleophiles in Ir-catalyzed asymmetric allylic substitution reactions, prochiral nucleophiles are less studied. We present a new prochiral nucleophile, namely, deconjugated butyrolactam, for Ir-catalyze

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode

The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.

Asymmetric Synthesis of γ-Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade

The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen cascade for the formal anti-Markovnikov hydroamination of allyl alcohols to synthesize optically enriched γ-secondary amino alcohols. By exploiting the Ru-(S)-iPrPyme catalyst with minimal stereogenicity, a cascade process including dehydrogenation, conjugate addition, and asymmetric reduction was developed. The mild conditions, functional group tolerance, and broad substrate scope (54 examples) demonstrate the synthetic practicality of the catalytic system.

Chemoselective α,β-Dehydrogenation of Saturated Amides

We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).

1,3-Dioxa-[3,3]-sigmatropic Oxo-Rearrangement of Substituted Allylic Carbamates: Scope and Mechanistic Studies

An unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment of aryl- and alkenyl-substituted allylic alcohols with activated isocyanates is reported. The reorganization of bonds is highly dependent on the electron density of the aromatic

Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination

Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a-1o with formaldehyde to form primary homoallylic alcohols 2a-2o with excellent control of regio- and enantioselectivity. These

Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.

Part 2. Notch-sparing γ-secretase inhibitors: The study of novel γ-amino naphthyl alcohols

One therapeutic approach for Alzheimer's disease is to inhibit the cleavage of the amyloid precursor protein (APP) by γ-secretase. At the beginning of a series of studies from our laboratories, a series of novel γ-amino alcohols (1) were found to possess γ-secretase inhibitory activity and Notch-sparing effects. A new one-pot synthesis of γ-amino alcohols and the structure-activity relationship (SAR) of these analogs will be discussed.