13269-47-1

Usage

Functional groups

Primary amine, alcohol, terminal double bond

Physical state

Colorless liquid

Boiling point

166-168°C

Solubility

Soluble in water and ethanol

Applications

a. Manufacturing of pharmaceuticals
b. Synthesis of various organic compounds
c. Reagent in organic chemistry reactions

Biological activity

Reactive intermediate in the biosynthetic pathway of certain plant alkaloids

InChI:InChI=1/C4H9NO/c1-2-4(6)3-5/h2,4,6H,1,3,5H2

Upstream product

• 930-22-3 epoxybutene 
• 7664-41-7 ammonia 
• 15667-63-7 2-acetoxy-3-butenenitrile 
• 89124-74-3 1-nitrobut-3-en-2-ol 
• 75-52-5 nitromethane 
• 107-02-8 acrolein 
• 1254120-10-9 1-azido-but-3-en-2-ol 
• 5809-59-6 3-cyano-3-hydroxy-1-propene 
• 134676-36-1 (2-Hydroxy-but-3-enyl)-carbamic acid tert-butyl ester 
• 40326-19-0 2-<(trimethylsilyl)oxy>-3-butenenitrile 
• 1595205-41-6 (R)-2-(2-hydroxylbut-3-enyl)isoindoline-1,3-dione 

Downstream Products

• 1072-93-1 (5R)-5-vinyl-1,3-oxazolidine-2-thione 
• 500-12-9 DL-5-vinyloxazolidine-2-thione (goitrin) 
• 620622-24-4 N-(p-methoxyphenylamino)-3-buten-2-ol 
• 1083074-03-6 C₁₇H₂₆N₂O₄ 

Relevant academic research and scientific papers

An improved synthesis of the antithyroid factor DL-goitrin

DL-1-Amino-3-buten-2-ol H2C=CH-CH(OH)-CH2NH2 has been synthesized in a satisfactory overall yield by reduction of the protected cyanohydrin H2C=CH-CH(OR)-CN with aluminum hydride, followed by removal of the protecting group with aqueous hydrochloric acid and treatment with potassium hydroxide.The amino alcohol is a key intermediate in a synthesis of the antithyroid goitrin reported previously.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Synthetic method of antiviral drug (R,S)-goitrine

The invention discloses a synthetic method of an antiviral drug (R,S)-goitrine. The synthesis method comprise the following steps: dissolving nitromethane in a proper solvent, adding acrolein, carrying out stirring at a set temperature for a period of time to obtain a solution A, dissolving triethylamine into residual nitromethane to obtain a solution B, dropwise adding the solution B into the solution A for a reaction, carrying out rotary evaporation to remove the solvent and unreacted nitromethane after the reaction is completed, and carrying out column chromatography separation on the obtained mixture to obtain 1-nitro-3-butenyl-2-ol; reducing nitro of the 1-nitro-3-butenyl-2-ol by an iron powder reduction method to obtain 1-amino-3-butenyl-2-ol; and further carrying out a cyclization reaction on the 1-amino-3-butenyl-2-ol with carbon disulfide to generate the (R,S)-goitrine. The synthetic method disclosed by the invention had the advantages of low cost, simple operation, safety andenvironmentally friendliness.

Preparation method of 5-vinyl-2-sulfo-oxazolidine

The invention discloses a preparation method of 5-vinyl-2-sulfo-oxazolidine. The preparation method comprises the following steps: (1) using acrolein and trimethylsilyl cyanide as raw materials for reaction under the catalysis of zinc iodide to obtain 2-[(trimethyorganosilyl)oxy]-3-butenenitrile; (2) in a toluene solution, using a red aluminum solution as a reducing agent and potassium carbonate and methanol as a desiliconizing agent, performing reduction and desiliconization on the 2-[(trimethyorganosilyl)oxy]-3-butenenitrile to obtain 1-amino-3-butene-2-alcohol; (3) enabling the 1-amino-3-butene-2-alcohol to react with carbon disulfide, and using hydrogen peroxide as a desulfurizing agent to obtain the 5-vinyl-2-sulfo-oxazolidine. The fatty chain cyanogroup used in the preparation methodis the red aluminum solution; compared with conventional lithium aluminum hydride, the red aluminum solution has simple operation conditions and is low in cost. In the reduction, methylbenzene, instead of traditional combustible liquid such as diethyl ether and the like, is used as a solvent, so that the reaction conditions are safer. In the annulations in the step (3), the hydrogen peroxide replaces original lead nitrate and serves as the desulfurizing agent, so that the pollution to the environment can be reduced, and the method is safe and environmentally-friendly.

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

SHORT-ACTING BENZODIAZEPINE DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF

The present invention relates to a benzodiazepine derivative of Formula I as a short-acting anesthetic, a pharmaceutical composition comprising the same, a kit comprising the same, a preparation method thereof, an method of anesthesia using the same and use thereof in the manufacture of an anesthetic medicament.

Preparation method of 2-hydroxyl-3-butene-1-amine

The invention discloses a preparation method of 2-hydroxyl-3-butene-1-amine. The preparation method comprises the following specific steps: (1) taking acrolein as a start raw material to react with trimethylsilyl cyanide at room temperature in the presence of lithium perchlorate trihydrate to obtain 2-hydroxyl-3-butene-1-nitrile; (2) with diethyl ether or tetrahydrofuran as a solvent, reducing the 2-hydroxyl-3-butene-1-nitrile with lithium aluminum hydride to obtain a crude product of 2-hydroxyl-3-butene-1-amine; (3) making the crude product of 2-hydroxyl-3-butene-1-amine react with hydrochloric acid to obtain 2-hydroxyl-3-butene-1-amine hydrochloride; and (4) making the 2-hydroxyl-3-butene-1-amine hydrochloride react with alkali to finally obtain the 2-hydroxyl-3-butene-1-amine. According to the method disclosed by the invention, without a trimethylsilyl protection group removal process, the operation of reduced pressure distillation is avoided, the reaction path is shortened, and the operation is simple.

Expedient synthesis of epigoitrin from L-ascorbic acid

Epigoitrin is the main bioactive constituent of an important traditional Chinese herbal medicine, Radix isatidis. Reported pharmacological effects of epigoitrin include antiviral, anticancer, and antithyroid activities. Extensive biological exploration of

METHOD FOR PRODUCING AMINO ALCOHOL COMPOUND

Provided is a novel method that can produce an amino alcohol compound (2). A method for producing an amino alcohol compound represented by the formula (2): wherein R1, R2, and R3 each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a hydrogen atom, the method including a step of reacting a compound represented by the formula (1): wherein R1, R2, and R3 each have the same meaning as defined above, with ammonia in the presence of a rare-earth element compound.

METHOD FOR PRODUCING AMINO ALCOHOL COMPOUND

Provided is a novel method that can produce an amino alcohol compound (2). A method for producing an amino alcohol compound represented by the formula (2): wherein R1, R2, and R3 each independently represent an alkyl group optionally having a substituent, an aryl group optionally having a substituent, or a hydrogen atom, the method including a step of reacting a compound represented by the formula (1): wherein R1, R2, and R3 each have the same meaning as defined above, with ammonia in the presence of a compound of Group 6 element in the periodic table.