793669-26-8

Basic information

• Product Name: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran
• Synonyms: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran;(2S*,2'R*)-Nebivolol Impurity C;(2R)-6-fluoro-2-[(2S)-oxiran-2-yl]-3,4-dihydro-2H-chromene
• CAS NO: 793669-26-8
• Molecular Formula: C11H11FO2
• Molecular Weight: 194.2
• Mol File: 793669-26-8.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-[(2S)-2-oxiranyl]-2H-1-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran(793669-26-8)
• EPA Substance Registry System: (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran(793669-26-8)

Safety Data

• Hazardous Substances Data: 793669-26-8(Hazardous Substances Data)

Usage

Description

(2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is a complex organic compound with a specific stereochemistry and functional groups. It is characterized by its fluorine atom at the 6th position, a 3,4-dihydro ring, and an oxirane (epoxide) group attached to the 2nd position of the benzopyran structure. (2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is likely to have unique chemical and biological properties due to its specific structural features.

Uses

Used in Pharmaceutical Industry:
(2R)-rel-6-Fluoro-3,4-dihydro-2-[(2S)-2-oxiranyl]-2H-1-benzopyran is used as an intermediate in the synthesis of Nebivolol (N387933), which is a cardioselective beta-1 receptor blocking agent. This application is significant because Nebivolol is utilized in the treatment of hypertension and other cardiovascular conditions, making this compound an essential part of the pharmaceutical development process.

Upstream product

• 303176-46-7 (R)-2-[(R)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]-2-hydroxyethyl-4-methylbenzenesulfonate 
• 371-41-5 4-Fluorophenol 
• 13990-72-2 1-allyloxy-4-fluorobenzene 
• 13997-72-3 1-allyl-2-hydroxy-5-fluorobenzene 
• 303176-38-7 5-(5-fluoro-2-hydroxy-phenyl)-E-2-penten-1-ol 
• 303176-45-6 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1R)-1,2-ethylene glycol 
• 303176-43-4 1-[6-fluoro-(2R)-3,4-dihydro-2H-benzopyran-2-yl]-(1S)-1,2-ethylene glycol 
• 303176-34-3 2-alllyl-1-(tert-butyldimethylsilyloxy)-4-fluoro-benzene 
• 783332-57-0 3-(2-((tert-butyldimethylsilyl)oxy)-5-fluorophenyl)propanal 
• 303176-35-4 3-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-1-propanol 
• 303176-37-6 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-(E)-2-penten-1-ol 
• 303176-36-5 ethyl 5-(2-tert-butyldimethylsilyloxy-5-fluoro-phenyl)-2-pentenoate 
• 303176-44-5 2-(1,2-di(4-nitrophenylcarbonyloxy)-(1R)-ethyl)-6-fluoro-(2R)-3H,4H-chromene 
• 793669-26-8 [1R*(R*)]-6-fluoro-3,4-dihydro-2-(oxiran-2-yl)-2H-chromene 

Downstream Products

• 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 
• 1421916-53-1 C₂₉H₃₁F₂NO₄ 
• 118457-14-0 (+)-Nebivolol 
• 929706-85-4 α,α'-[[(phenylmethyl)imino]bismethylene]bis-[6-fluoro-3,4-dihydro-2H-1-benzopyran-2-methanol] 
• 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 
• 152520-56-4 DL-nebivolol hydrochloride 
• 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 
• 897661-66-4 (S*)-2-amino-1-((R*)-6-fluorochroman-2-yl)ethanol 
• 905454-41-3 2-amino-1-[6-fluoro-(2R)-3H,4H-2-chromenyl]-(1S)-ethan-1-ol 
• 1345202-53-0 (2S)-2-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)-2-{[(4-methylphenyl)sulfonyl]oxy}ethyl acetate 
• 152520-56-4 nebivolol hydrochloride 

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.

Method for preparing nebivolol hydrochloride epoxy intermediate 6-fluoro-2-epoxy ethyl chroman

The invention discloses a method for preparing a nebivolol hydrochloride epoxy intermediate 6-fluoro-2-epoxy ethyl chroman. The method includes the following steps that firstly, under the conditions that water, phosphate, inorganic alkali B1, zinc chloride, a hydrogen source, aldose reductase and NADPH exist, the temperature is 30-70 DEG C and the pH value is 6.0-8.0, a reduction reaction happens to 2-chloro-1-(6-fluorochromane-2-yl)-ethanon, and 2-chloro-1-(6-fluorochromane-2-yl)-alcohol is obtained; secondly, 2-chloro-1-(6-fluorochromane-2-yl)-alcohol is heated in a C1-C6 alkanol solvent and inorganic alkali B2 for a reflux reaction, an organic ester solvent is added dropwise for crystallization after the reaction ends, and 6-fluoro-2-epoxy ethyl chroman is obtained. The preparation method is mild in reaction condition, raw materials and solvents are easy to obtain, and the method is suitable for industrial production.