54313-33-6

Basic information

• Product Name: Benzeneacetyl chloride, 4-methoxy-3-(phenylmethoxy)-
• CAS NO: 54313-33-6
• Molecular Formula: C16H15ClO3
• Molecular Weight: 290.746
• Mol File: 54313-33-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Benzeneacetyl chloride, 4-methoxy-3-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetyl chloride, 4-methoxy-3-(phenylmethoxy)-(54313-33-6)
• EPA Substance Registry System: Benzeneacetyl chloride, 4-methoxy-3-(phenylmethoxy)-(54313-33-6)

Safety Data

• Hazardous Substances Data: 54313-33-6(Hazardous Substances Data)

Upstream product

• 5487-33-2 O-benzylhomoisovanillic acid 
• 100-39-0 benzyl bromide 
• 90047-72-6 1-(3-(benzyloxy)-4-methoxyphenyl)-2,2,2-trichloroethanol 
• 1131-94-8 homoisovanillic acid 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 1699-39-4 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 1699-38-3 3-benzyloxy-4-methoxy-benzyl chloride 
• 1860-60-2 3-benzyloxy-4-methoxy-benzyl alcohol 
• 621-59-0 isovanillin 

Downstream Products

• 21411-26-7 N-[3-(benzyloxy)-4-methoxyphenethyl]-2-[3-(benzyloxy)-4-methoxyphenyl]acetamide 
• 485-19-8 (R)-reticuline 
• 605-34-5 (S)-scoulerine 
• 70614-67-4 1-(3-benzyloxy-4-methoxybenzyl)-7-benzyloxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 1699-46-3 reticuline 
• 854668-31-8 1-(3-benzyloxy-4-methoxy-phenyl)-3-diazo-acetone 
• 73168-78-2 N-(3,4-methylenedioxyphenethyl)-3-benzyloxy-4-methoxyphenylacetic acid amide 
• 1253735-93-1 C₅₁H₄₆BrNO₈ 

Relevant articles and documents

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Synthesis and initial preclinical evaluation of the P2X7 receptor antagonist [11C]A-740003 as a novel tracer of neuroinflammation

Neuroinflammation, in particular activation of microglia, is thought to play an important role in the progression of neurodegenerative diseases. In activated microglia, the purinergic P2X7 receptor is upregulated. A-740003, a highly affine and

Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.