5399-06-4

Basic information

• Product Name: 4-(2-NAPHTHYLTHIOACETYL)MORPHOLINE
• Synonyms: 1-Morpholino-2-(2-naphtyl)-1-ethanethione;1-Morpholino-2-(2-naphtyl)ethanethione;4-(2-Naphtylthioacetyl)morpholine;4-[(2-Naphtyl)thioacetyl]morpholine;4-[2-(2-Naphthalenyl)-1-thioxoethyl]morpholine;Brn 0216145;Morpholine, 4-(2-(2-naphthalenyl)-1-thioxoethyl)- (9ci);Morpholine, 4-(2-naphthylthioacetyl)-
• CAS NO: 5399-06-4
• Molecular Formula: C₁₆H₁₇NOS
• Molecular Weight: 271.384
• Mol File: 5399-06-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 426°Cat760mmHg
• Flash Point: 211.4°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 4.44E-08mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 4-(2-NAPHTHYLTHIOACETYL)MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-NAPHTHYLTHIOACETYL)MORPHOLINE(5399-06-4)
• EPA Substance Registry System: 4-(2-NAPHTHYLTHIOACETYL)MORPHOLINE(5399-06-4)

Safety Data

• Hazardous Substances Data: 5399-06-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H17NOS/c19-16(17-7-9-18-10-8-17)12-13-5-6-14-3-1-2-4-15(14)11-13/h1-6,11H,7-10,12H2

Upstream product

• 110-91-8 morpholine 
• 93-08-3 methyl 2-naphthyl ketone 
• 77414-52-9 4-(naphthalen-2-yl)-1,2,3-thiadiazole 
• 827-54-3 2-naphthylethylene 
• 1033590-39-4 2‐morpholino‐1‐(naphthalen‐2‐yl)‐2‐thioxoethan‐1‐one 

Downstream Products

• 581-96-4 2-naphthylacetic acid 
• 1417706-43-4 C₂₇H₂₅NO₃S 
• 1417706-42-3 C₂₆H₂₃NO₃S 
• 1393898-16-2 5-(morpholin-4-yl)-4-(naphthalen-2-yl)-3-phenylthiophen-2(3H)-one 
• 126572-93-8 4-[(E)-2-Naphthalen-2-yl-1-(2-nitro-phenyldisulfanyl)-2-(2-nitro-phenylsulfanyl)-vinyl]-morpholine 

Relevant articles and documents

Optimizing the Pharmacological Profile of New Bifunctional Antihyperlipidemic/Antioxidant Morpholine Derivatives

Among the causal risk factors directly promoting the development of coronary and peripheral atherosclerosis are reactive oxygen species and elevated low-density lipoprotein plasma levels. We hereby designed new potent squalene synthase (SQS) inhibitors that may simultaneously tackle the oxidative stress induced by lipid peroxidation. Using previously developed morpholine derivatives as a starting point, we conducted extensive structural changes by either substituting or modifying the morpholine ring, aiming at an optimal SQS-antioxidant pharmacological profile. Compounds 2, 3, and 7 emerged as the most potent bifunctional analogues, displaying IC50 values for SQS inhibition of 0.014, 0.16, and 0.51 μM, respectively, and further significantly decreasing lipid peroxidation of hepatic microsomal membranes. The aforementioned activities were also confirmed in vivo since the most promising derivative 2 exhibited a remarkable antihyperlipidemic and antioxidant effect. In conclusion, rational drug design accompanied by structure-activity relationship studies led to compounds combining improved antioxidant and antihyperlipidemic activity that may serve as multifunctional agents against atherosclerosis.

METHOD FOR MANUFACTURING AROMATIC NITRILE COMPOUND

The present invention provides a method for industrially producing a highly pure aromatic nitrile compound and a highly pure aromatic carboxylic acid compound safely and highly efficiently at low costs. Compound (2) is subjected to Willgerodt reaction in the presence of an additive as necessary, and the obtained amide compound (3) is hydrolyzed and neutralized to give carboxylic acid compound (4). Carboxylic acid compound (4) is reacted with a halogenating agent in the presence of a catalyst as necessary in an organic solvent, and further reacted with an amidating agent, and the obtained amide compound (5) or (6) is reacted with a dehydrating agent to give nitrile compound (1). Alternatively, carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in the presence of a catalyst as necessary in an organic solvent to give nitrile compound (1). Np is a naphthyl group optionally having substituent(s), R5 is an alkylene group having 1-3 carbon atoms, and other symbols are as described in the DESCRIPTION.

Selective reduction of carbonyl groups in the presence of low-valent titanium reagents

The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.