876514-31-7

Basic information

• Product Name: (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran
• Synonyms: (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran;(2S*,2'S*)-Nebivolol Impurity C;(2S)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene
• CAS NO: 876514-31-7
• Molecular Formula: C11H11FO2
• Molecular Weight: 194.2
• Mol File: 876514-31-7.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 292℃
• Flash Point: 138℃
• Appearance: /
• Density: 1.299
• CAS DataBase Reference: (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran(876514-31-7)
• EPA Substance Registry System: (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran(876514-31-7)

Safety Data

• Hazardous Substances Data: 876514-31-7(Hazardous Substances Data)

Usage

General Description

The chemical compound (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran, also known as (2R)-rel-6-Fluoro-dihydro-oxiranyl-benzopyran, is a complex organic molecule with potential pharmacological properties. It has a fluoro-substituted benzopyran structure with an oxiranyl group attached to it. (2R)-rel-6-Fluoro-3,4-dihydro-2-(2R)-2-oxiranyl-2H-1-benzopyran may have potential use in medicinal chemistry due to its ability to interact with biological systems, such as enzymes or receptors, and potentially exhibit pharmaceutical activity. Its specific biological and pharmacological properties would need to be further investigated in order to determine its potential use in drug development.

Upstream product

• 371-41-5 4-Fluorophenol 
• 409346-73-2 6-fluoro-3,4-dihydro-2H-1-benzopyran-2-carboxaldehyde 
• 2181-42-2 trimethylsulphonium iodide 
• 1219915-05-5 (S)-6-fluoro-2-(oxiran-2-yl)chroman 
• 100-46-9 benzylamine 
• 99199-61-8 6-fluoro-3,4-dihydro-2H-benzopyran-2-carboxylic acid ethyl ester 
• 129101-37-7 (R)-6-fluorochroman-2-carboxylic acid 
• 1219914-99-4 2-chloro-1-[(2R)-6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl]ethan-1-one 
• 1219915-02-2 (S)-2-chloro-1-((R)-6-fluoro-1-benzopyran-2-yl)-ethanol 
• 1388095-25-7 C₁₆H₁₉FO₄ 
• 1388095-27-9 C₁₆H₁₈ClFO₄ 
• 783332-57-0 3-(2-((tert-butyldimethylsilyl)oxy)-5-fluorophenyl)propanal 
• 303176-34-3 2-alllyl-1-(tert-butyldimethylsilyloxy)-4-fluoro-benzene 
• 303176-43-4 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 

Downstream Products

• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 793669-26-8 [1S*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 
• 905454-57-1 1-[6-fluoro-(2S)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 
• 197706-50-6 6-fluoro-(2R)-2-[(2R)-2-oxiranyl]-3,4-dihydrobenzopyran 
• 1030385-17-1 (SRRR)-d-N-benzilnebivolol 
• 1199945-26-0 2-{benzyl-[2-(6-fluoro-chroman-2-yl)-2-hydroxy-ethyl]-amino}-1-(6-fluoro-chroman-2-yl)-ethanol 
• 1345202-53-0 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl acetate 
• 118457-14-0 (+)-Nebivolol 
• 152520-56-4 nebivolol hydrochloride 
• 152520-56-4 DL-nebivolol hydrochloride 
• 897661-66-4 (S*)-2-amino-1-((R*)-6-fluorochroman-2-yl)ethanol 
• 1421916-53-1 C₂₉H₃₁F₂NO₄ 
• 905454-41-3 2-amino-1-[6-fluoro-(2R)-3H,4H-2-chromenyl]-(1S)-ethan-1-ol 
• 929706-85-4 α,α'-[[(phenylmethyl)imino]bismethylene]bis-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] 

Relevant articles and documents

Preparation method and application of Smo inhibitor based on Nebivolol

The invention discloses a preparation method and an application of a Smo inhibitor based on Nebivolol. The structural formula of the Smo inhibitor is as shown in a formula (I). The invention further discloses a synthetic method and an application of the Smo inhibitor. According to the Smo inhibitor, a beta-receptor retardant Nebivolol with inhibitory activity for Smo proteins serves as a lead compound, and optimization reconstruction is implemented based on the beta-receptor retardant Nebivolol to obtain the Smo inhibitor with good inhibitory activity.

Studies directed toward the exploitation of vicinal diols in the synthesis of (+)-nebivolol intermediates

While the exploitation of the Sharpless asymmetric dihydroxylation as the source of chirality in the synthesis of acyclic molecules and saturated heterocycles has been tremendous, its synthetic utility toward chiral benzo-annulated heterocycles is relatively limited. Thus, in the search for wider applications of Sharpless asymmetric dihydroxylation-derived diols for the synthesis of benzo-annulated heterocycles, we report herein our studies in the asymmetric synthesis of (R)-1-((R)-6-fluorochroman-2-yl)ethane-1,2-diol, (R)-1-((S)-6-fluorochroman-2-yl)ethane-1,2-diol and (S)-6-fluoro-2-((R)-oxiran-2-yl)chroman, which have been used as late-stage intermediates for the asymmetric synthesis of the antihypertensive drug (S,R,R,R)-nebivolol. Noteworthy is that a large number of racemic and asymmetric syntheses of nebivolol and their intermediates have been described in the literature, however, the Sharpless asymmetric dihydroxylation has never been employed as the sole source of chirality for this purpose.

Preparation of 6-fluoro -3,4-dihydro -2H-1-benzopyran-2-oxirane improved method

The invention relates to an improvement method for preparing a nebivolol key intermediate, namely 6-fluorin-3,4-dihydro-2H-1-benzopyranyl-2-epoxy ethane. The method comprises the following steps of: (a) condensing a compound (IV) and dihalogenated methane in the presence of an organic metal lithium compound to obtain a compound (II); (b) reducing the compound (II) to obtain a compound (III); and (c) performing cyclization on the compound (III) under alkaline condition to obtain a compound (I). The scheme of the invention has the advantages of readily available raw materials, easiness in operating, greatly increased reaction yield and purity and high contribution to industrial mass production.