75611-78-8

Basic information

• Product Name: 6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-TRANS-4-(1-PYRROLIDINYL)-2H-BENZO-[B]-PYRANO-3-OL
• Synonyms: 6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-TRANS-4-(1-PYRROLIDINYL)-2H-BENZO-[B]-PYRANO-3-OL;(3R,4S)-rel-3,4-Dihydro-3-hydroxy-2,2-diMethyl-4-(1-pyrrolidinyl)-2H-1-benzopyran-6-carbonitrile
• CAS NO: 75611-78-8
• Molecular Formula: C16H20N2O2
• Molecular Weight: 272.34
• Product Categories: Miscellaneous Reagents;Drug Analogues
• Mol File: 75611-78-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 395.848°C at 760 mmHg
• Flash Point: 193.202°C
• Appearance: /
• Density: 1.231g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-TRANS-4-(1-PYRROLIDINYL)-2H-BENZO-[B]-PYRANO-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-TRANS-4-(1-PYRROLIDINYL)-2H-BENZO-[B]-PYRANO-3-OL(75611-78-8)
• EPA Substance Registry System: 6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-TRANS-4-(1-PYRROLIDINYL)-2H-BENZO-[B]-PYRANO-3-OL(75611-78-8)

Safety Data

• Hazardous Substances Data: 75611-78-8(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

6-Cyano-3,4-dihydro-2,2-diMethyl-trans-4-(1-pyrrolidinyl)-2H-benzo-[b]-pyrano-3-ol is an analogue of Cromakalin, which causes vasodilation by activation of potassim channels.

InChI:InChI=1/C16H20N2O2/c1-16(2)15(19)14(18-7-3-4-8-18)12-9-11(10-17)5-6-13(12)20-16/h5-6,9,14-15,19H,3-4,7-8H2,1-2H3/t14-,15+/m1/s1

Upstream product

• 123-75-1 pyrrolidine 
• 65018-90-8 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 
• 65018-89-5 trans-3-bromo-3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-chromene-6-carbonitrile 
• 33143-29-2 6-cyano-2,2-dimethylchromene 
• 33143-92-9 4-[(1,1-Dimethyl-2-propynyl)oxy]benzonitrile 

Relevant articles and documents

Synthesis and antihypertensive activity of substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols

A series of novel substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols was prepared and tested for antihypertensive activity in the conscious deoxycorticosterone acetate (DOCA)/saline treated hypertensive rat. Optimum blood pressure lowering activity requires 6-substitution by a strong electron-withdrawing group, together with a pyrrolidino or piperidino group at the 4 position. Exceptions to this were the 7-nitro-4-pyrrolidine analogue and the 6-nitro-3-chloropropylamine, which retained marked antihypertensive activity. All of these compounds were direct vasodilators and had comparable antihypertensive activity to hydralazine and to the calcium antagonist, nifedipine. The synthetic route to these compounds involves cyclization of propargyl ethers to 2H-1-benzopyrans, followed by conversion via bromohydrins to 3,4-epoxides, which were ring opened with the appropriate amines. Meta-substituted propargyl ethers gave both 5- and 7-substituted benzopyrans on thermal cyclization, the former predominating. A new route to 2,2-dimethyl-7-nitrobenzopyran is described.