74007-21-9

Basic information

• Product Name: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide
• Synonyms: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide
• CAS NO: 74007-21-9
• Molecular Weight: 315.369
• Mol File: 74007-21-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide(74007-21-9)
• EPA Substance Registry System: N-<2-(3-methoxyphenyl)ethyl>(3-hydroxy-4-methoxyphenyl)acetamide(74007-21-9)

Safety Data

• Hazardous Substances Data: 74007-21-9(Hazardous Substances Data)

Upstream product

• 89936-29-8 2-(3,5-dibromo-4-methoxyphenyl)acetic acid 
• 774-81-2 (3-bromo-4-methoxy-phenyl)-acetic acid 
• 104-01-8 4-Methoxyphenylacetic acid 
• 1131-94-8 homoisovanillic acid 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 

Downstream Products

• 23180-27-0 1-(3'-hydroxy-4'-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 58780-17-9 5-(2-formyl-6-methoxy-1,2,3,4,5,8-hexahydro-isoquinolin-1-ylmethyl)-2-methoxy-phenol 
• 23180-28-1 6-methoxy-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4,5,8-hexahydroisoquinoline 
• 54186-35-5 1-(2-bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one 
• 54186-36-6 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,6,7,8-hexahydroisoquinolin-6-one 
• 74007-24-2 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-1,3,4,5,7,8-hexahydroisoquinolin-6-one 
• 74007-22-0 C₂₀H₂₅NO₅ 
• 74007-23-1 1-(2'-bromo-4'-methoxy-5'-hydroxybenzyl)-2-formyl-6-ketal-1,3,4,5,7,8-hexahydroisoquinoline 
• 74007-25-3 1-(2-Bromo-5-hydroxy-4-methoxy-benzyl)-1,3,4,5,7,8-hexahydro-2H-isoquinolin-6-one 
• 1395084-82-8 C₁₉H₂₃NO₃ 
• 1395084-76-0 2-methoxy-5-{2-[2-(3-methoxyphenyl)ethylamino]ethyl}phenol 
• 95427-40-0 1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-3,4-dihydroisoquinoline 
• 1033384-84-7 C₁₈H₁₉NO₃*H₃O₄P 
• 1033384-71-2 C₁₉H₂₃NO₆S 

Relevant articles and documents

A new class of selective and potent 7-dehydrocholesterol reductase inhibitors

We prepared a number of N-phenethyltetrahydroisoquinolines structurally related to protoberberines. They were tested for activity against bacteria, fungi, and human leukemia HL-60 cells and also for inhibition of biosynthesis: ergosterol in yeasts and cholesterol in human cells. In the latter assay panel, several of the compounds were distinguished by a strong and selective inhibition of 7-dehydrocholesterol reductase (7-DHCR, EC 1.3.1.21), an enzyme responsible for the conversion of 7-dehydrocholesterol to cholesterol in the last step of cholesterol biosynthesis. In a whole-cell assay, the most active compound 5f showed a much stronger inhibition of overall cholesterol biosynthesis (IC 50 2.3 nM) than BM 15.766 (IC50 500 nM), presently the most selective known inhibitor of 7-DHCR. Since a defect of 7-dehydrocholesterol reductase is associated with Smith-Lemli-Opitz syndrome (SLOS), the potent and selective inhibitors reported here will enable more detailed investigation of the pathogenesis of SLOS.

Chemistry of opium alkaloids, 45. Improvements in the total synthesis of morphine

The chiral 1,2,3,4-tetrahydroisoquinoline intermediates in the Price and Beyerman routes to morphine, (+)-(R)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy- 1,2,3,4-tetrahydroisoquinoline (6) and (+)-(R)-1-(3,5-dibenzyloxy-4- methoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (5), were prepared in high ee by ruthenium-catalyzed asymmetric transfer hydrogenation of the corresponding imine precursors (Noyori method). The yield of the key raw material in the Beyerman route, 3,5-dibenzyloxy-4-methoxyphenylacetric acid (1), starting from gallic acid methyl ester (7) was improved by a factor of 5 over previously described syntheses. Key steps in the new procedure are the selective formation of methyl 3,5-dihydroxy-4-methoxybenzoate (9) via the 3,5-diacetate and an improved benzylation of the hydroxyl groups in 9.

Synthetic Opium Alkaloids and Derivatives. A Short Total Synthesis of (+/-)-Dihydrothebainone, (+/-)-Dihydrocodeinone, and (+/-)-Nordihydrocodeinone as an Approach to a Practical Synthesis of Morphine, Codeine, and Congeners.

Racemic dihydrothebainone (19), nordihydrocodeinone (21), and dihydrocodeinone (22) were synthesized in high overall yield from 3-methoxyphenethylamine (4), via the key intermediate (+/-)-1-bromonordihydrothebainone (18); the route utilized unprotected ph