6066-49-5

Usage

Uses

Used in Pharmaceutical Industry:
3-n-Butylphthalide is used as a cardiovascular drug for the treatment of cerebral ischemic stroke. Its application in this field is attributed to its ability to improve blood flow and reduce the risk of stroke-related complications.
Used in Flavor and Fragrance Industry:
Given its warm, spicy herbaceous odor, 3-n-Butylphthalide is used as a flavoring agent and fragrance component in the food and beverage industry. Its distinct aroma makes it a valuable addition to various products, enhancing their sensory appeal and consumer experience.

Preparation

From celery oil; from phthalide via bromination and subsequent reaction of the resulting phthalidic acid with n-butyl magnesium bromide.

InChI:InChI=1/C41H34ClFIN3O7/c1-54-33-19-22(18-32(44)36(33)49)35-28-14-15-29-34(39(52)46(37(29)50)17-16-21-2-12-27(48)13-3-21)30(28)20-31-38(51)47(45-26-10-8-25(43)9-11-26)40(53)41(31,35)23-4-6-24(42)7-5-23/h2-14,18-19,29-31,34-35,45,48-49H,15-17,20H2,1H3

Upstream product

• 551-08-6 3-butylidenephthalide 
• 109-65-9 1-bromo-butane 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 693-03-8 n-butyl magnesium bromide 
• 111943-60-3 3-(4-iodobutyl)isobenzofuran-1(3H)-one 
• 6697-07-0 sedanonic acid 
• 110-62-3 pentanal 
• 124-38-9 carbon dioxide 
• 92-85-3 Thianthrene 
• 162050-42-2 3-hydroxy-3-butyl-1(3H)-isobenzofuranone 
• 119-67-5 o-carboxybenzaldehyde 
• 64624-87-9 2-(1-oxypentyl)-benzoic acid methyl ester 
• 425642-59-7 3-butyl-4-vinylphthalide 
• 1119-90-0 di-n-butylzinc 

Downstream Products

• 380905-53-3 (R)-2-(1-hydroxy-n-pentyl)benzoic acid 
• 1330531-02-6 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester 
• 1330531-03-7 (±)-(E)-2-methoxy-4-(3-(4-(nitrooxy)butoxy)-3-oxoprop-1-en-1-yl)phenyl 2-(1-(2-chloroacetoxy)pentyl)benzoate 
• 1330531-04-8 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester 
• 1330531-05-9 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester 
• 1330531-06-0 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester 
• 1330531-07-1 (+/-)-(E)-2-(2-chloroacetoxypentyl)benzoic acid {4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester 
• 1330531-08-2 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-09-3 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-10-6 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-11-7 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-12-8 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(4-nitrooxybutoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-13-9 (+/-)-(E)-2-[2-(diethylaminoacetoxy)pentyl]benzoic acid {2-methoxy-4-[2-(5-nitrooxypentoxycarbonyl)vinyl]}phenyl ester hydrochloride 
• 1330531-14-0 (+/-)-(E)-2-[2-(morpholinoacetoxy)pentyl]benzoic acid {4-[2-(3-nitrooxypropoxycarbonyl)vinyl]}phenyl ester hydrochloride 

Relevant academic research and scientific papers

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Method for synthesizing butyl phthalide

The invention relates to a method for synthesizing butyl phthalide. The synthesis of butyl phthalide is realized through the reduction/lactonization cascade reaction of o-valeryl benzoate. Copper salt, silane and a phosphine ligand form a CuH reducing agent in an organic solvent, ketone carbonyl of o-valeryl benzoate is selectively reduced at the temperature of 0-40 DEG C, lactonization reaction is spontaneously performed under the reaction condition, and butyl phthalide is generated. The molar ratio of the copper salt to the phosphine ligand to silane to o-valeryl benzoate is (0.02-0.08): (0.02-0.08): (2-5): 1. According to the method, reaction under a high-temperature condition is not needed, and the yield is also obviously improved; no cadmium reagent or other reagents with high toxicity is used, so that the method is environment-friendly; the catalytic amount of CuH catalyst used in the method has the advantages of high yield and the like.

Novel purification method of butylphthalide

The invention aims to provide a simple and easy-to-operate method for preparing high-purity butylphthalide. The method comprises the following steps: subjecting o-formylbenzoic acid to reacting with a Grignard reagent to prepare a reaction solution of butylphthalide, regulating the reaction solution to a certain pH value by using a specific acid at a certain temperature, extracting a product by using an organic solvent, and washing an organic phase by using an alkali so as to obtain high-purity butylphthalide. According to the method, silica gel column chromatography or a high-temperature and high-vacuum distillation method is not used; tedious multiple acid and alkali adjusting procedures for purifying butylphthalide is avoided; operation is simple and effective; and the method is suitable for industrial large-scale production.

Butylphthalide ring-opening compound, pharmaceutical compound, and preparation methods, compositions and applications of butylphthalide ring-opening compound and pharmaceutical compound

The invention relates to the field of medicines, and in particular, relates to a butylphthalide ring-opening compound, a pharmaceutical compound and preparation methods and applications of the butylphthalide ring-opening compound and the pharmaceutical compound. The butylphthalide ring-opening compound has a structure represented by a formula (I), wherein R1 and R2 are the same or different and are independently selected from H, C1-C5 alkyl, C1-C5 hetero-alkyl and -SO2R6, and R6 is selected from H, C1-C5 alkyl, C1-C5 hetero-alkyl, an aromatic ring and a heterocyclic ring from a three-membered ring to an eight-membered ring; or R1 and R2 are connected to form a three-membered ring to an eight-membered ring; and X is C or N or is absent to form a five-membered ring or a six-membered ring. The compound can be fully absorbed by the human body by being combined with an active substance, and the biological activity of the active substance is further promoted. Particularly, after the compound is combined with edaravone, a compound with excellent biological activity can be obtained.

Preparation method of butylphthalide

The invention discloses a of butylphthalide. The preparation method comprises the following steps: with phthalic anhydride as a starting material, carrying out condensation, hydrolysis, reduction andesterification reactions to obtain butylphthalide. According to the preparation method, reaction raw materials are easy to obtain, operation is simple, reaction conditions are relatively mild, requirements on equipment is low, crude drugs with a purity of more than 99.80% and meeting medicinal requirements can be obtained without rectification, and the preparation method is suitable for industrialproduction.

Method for synthesizing 3 - n -butyl - l (3H)-isobenzofuranone (by machine translation)

The invention discloses a method for synthesizing 3 - n -butyl - l (3H)-isobenzofuranone, firstly mixing Grignard reagent with Lewis acid, adjusting pH to acidity by an acid reagent, extracting with an organic solvent, concentrating and removing an organic solvent to obtain 3 - n -butyl - l (3H)-isobenzofuranone. (by machine translation)

Study on the ArI-catalyzed intramolecularoxy-cyclization of 2-alkenylbenzamides to benzoiminolactones

A new intramolecularoxy-cyclization of 2-alkenylbenzamides catalyzed by ArI has been developed. This protocol is highlighted by its metal-free catalytic system and extremely short reaction time, providing efficient and straightforward access to various benzoiminolactones in good to excellent yields. Interestingly, a regioselective transformation occurred when using two different reaction systems. Mechanistic studies suggested thatmCPBA acts as both oxidant and ligand at the IIIIcenter, and the Lewis acid BF3accelerated ligand exchange and reductive elimination in the catalytic process.

Design, Synthesis and Antifungal Activities of 6-Substituted 3-Butylphthalide Derivatives against Phytopathogenic Fungi

In order to discover novel potential antifungal agents, a series of 6-substituted 3-butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3-butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3-butyl-6-nitro-2-benzofuran-1(3H)-one and 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3-butyl-6-nitro-2-benzofuran-1(3H)-one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3-butyl-6-hydroxy-5-nitro-2-benzofuran-1(3H)-one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated.

α-Angelica lactone catalyzed oxidation of benzylic sp3C-H bonds of isochromans and phthalans

A metal-free organocatalytic system has been developed for highly efficient benzylic C-H oxygenations of cyclic ethers using oxygen as an oxidant. This oxidation reaction utilizes α-angelica lactone as a low cost/low molecular weight catalyst. The optimized reaction conditions allow the synthesis of valued isocoumarins and phthalides from readily available precursors in good yields. Mechanistic studies indicate that the reaction pathway likely involves a radical processviaa peroxide intermediate.

Purification method of 3-n-butyl-1-(3H)-isobenzofuranone

The invention discloses a purification method of 3-n-butyl-1-(3H)-isobenzofuranone, which mainly comprises the following steps: mixing a 3-n-butyl-1-(3H)-isobenzofuranone crude product with water, andregulating the pH value to be alkaline by using an alkaline reagent; extracting with an organic solvent, collecting an organic phase, and removing the solvent. According to the purification method disclosed by the invention, a high-purity product can be obtained without high-temperature and high-vacuum distillation, so that the operation is simple, the raw materials are easy to obtain, the yieldis high, the cost is low, and the industrialization prospect is better.