Isopropyl adamantane-1-carboxylate

Base Information

• Chemical Name: Isopropyl adamantane-1-carboxylate
• CAS No.: 24556-16-9
• Molecular Formula: C14H22O2
• Molecular Weight: 222.327
• Hs Code.: 2916209090
• DSSTox Substance ID: DTXSID10342882
• Nikkaji Number: J1.649.747I
• Wikidata: Q72436534
• Mol file: 24556-16-9.mol

Synonyms:isopropyl adamantane-1-carboxylate;24556-16-9;propan-2-yl adamantane-1-carboxylate;Tricyclo[3.3.1.13,7]decane-1-carboxylic acid, 1-methylethyl ester;Isopropyl 1-adamantanecarboxylate;Isopropyladamantane-1-carboxylate;SCHEMBL16731832;DTXSID10342882;Isopropyl 1-adamantanecarboxylate #;MFCD00193926;AKOS002263011;1-Adamantanecarboxylic acid, isopropyl ester;Adamantane-1-carboxylic acid isopropyl ester;(3r,5r,7r)-isopropyl adamantane-1-carboxylate;F3095-4872

Chemical Property of Isopropyl adamantane-1-carboxylate

Chemical Property:

• Melting Point: 29-30℃
• Boiling Point: 265.9±8.0℃ (760 Torr)
• Flash Point: 115.0±6.0℃
• PSA: 26.30000
• Density: 1.083±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.15440
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 222.161979940
• Heavy Atom Count: 16
• Complexity: 265

Purity/Quality:

98%Min ^*data from raw suppliers

Isopropyl adamantane-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C12CC3CC(C1)CC(C3)C2

Technology Process of Isopropyl adamantane-1-carboxylate

There total 3 articles about Isopropyl adamantane-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2-iodo-propane (75-30-9) + 1-Adamantanecarboxylic acid (828-51-3) → adamantane-1-carboxylic acid isopropyl ester (24556-16-9)

Guidance literature:

With N(Et)4⁽¹⁺⁾*(2-pyrrolidone-anion); In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1021/jo00354a030

Reference yield: 68.0%

1-Adamantanecarbonyl chloride (2094-72-6) → 1-(adamantan-1-yl)-2-methylpropan-1-one (68715-12-8) + (1-adamantanyl)methyl 1-adamantanecarboxylate (78679-70-6) + α-isopropyl-1-adamantemethanol + adamantane-1-carboxylic acid isopropyl ester (24556-16-9)

Guidance literature:

With cuprous halogenide; In diethyl ether; for 1h; Heating;

Reference yield:

1-Adamantanecarboxylic acid (828-51-3) → 1-adamantanemethanol (770-71-8) + adamantane-1-carboxylic acid isopropyl ester (24556-16-9)

Guidance literature:

With isopropyl alcohol; zirconium(IV) oxide; In gas; at 300 ℃; Yield given. Yields of byproduct given;

upstream raw materials:

2-iodo-propane

1-Adamantanecarboxylic acid

1-Adamantanecarbonyl chloride

Downstream raw materials:

1-adamantanecarbonitrile

Refernces

• 1、 Shono, Tatsuya,Ishige, Osamu,Uyama, Hiroshi,Kashimura, Shigenori. "A Novel Base Useful for Synthesis of Esters and Macrolides". . p. 546 - 549. Retrieved 2007/10/02.
• 2、 Barton, Derek H. R.,Elliott, John D.,Gero, Stephen D.. "The Synthesis and Properties of a Series of Strong but Hindered Organic Bases". . p. 1136 - 1137. Retrieved 2007/10/02.