Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate

Base Information

• Chemical Name: Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate
• CAS No.: 41301-44-4
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.181
• ChEMBL ID: CHEMBL2253384
• Nikkaji Number: J313.909C
• Mol file: 41301-44-4.mol

Synonyms:SCHEMBL1150726;CHEMBL2253384;KVSRWNPBUMDYOQ-NTSWFWBYSA-N;methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate;methyl (+/-)-trans-2,2-dimethyl-3-formylcyclopropanecarboxylate

Chemical Property of Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate

Chemical Property:

• Vapor Pressure: 0.652mmHg at 25°C
• Refractive Index: 1.511
• Boiling Point: 186.8 °C at 760 mmHg
• Flash Point: 69.2 °C
• PSA: 43.37000
• Density: 1.149 g/cm³
• LogP: 0.63050
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C1C(=O)OC)C=O)C
• Isomeric SMILES: CC1([C@H]([C@@H]1C(=O)OC)C=O)C

Technology Process of Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate

There total 25 articles about Methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate 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: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (1R,4R,5S)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexa-2-one (26771-21-1) → methyl (+/-)-cis-3-formyl-2,2-dimethyl-1-cyclopropanecarboxylate (26770-99-0,27335-33-7,27335-34-8,41301-44-4,51424-62-5,55701-02-5,62138-41-4,67968-42-7,84710-48-5)

Guidance literature:

In diethyl ether; ethyl acetate; at -10 ℃; for 1h;

Reference yield: 89.0%

(1R,3S)-3-Chlorocarbonyl-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester (76842-28-9,120591-67-5) → methyl (+/-)-cis-3-formyl-2,2-dimethyl-1-cyclopropanecarboxylate (26770-99-0,27335-33-7,27335-34-8,41301-44-4,51424-62-5,55701-02-5,62138-41-4,67968-42-7,84710-48-5)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In acetone; for 0.666667h; under 1241.2 Torr; Ambient temperature;

Reference yield: 61.0%

(1S,3R)-3-(1,2-Dihydroxy-2-methyl-propyl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester → methyl (+/-)-cis-3-formyl-2,2-dimethyl-1-cyclopropanecarboxylate (26770-99-0,27335-33-7,27335-34-8,41301-44-4,51424-62-5,55701-02-5,62138-41-4,67968-42-7,84710-48-5)

Guidance literature:

With sodium periodate; phosphate buffer; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(02)01270-4

upstream raw materials:

(1S,3R)-2,2-Dimethyl-3-((1E,3E)-penta-1,3-dienyl)-cyclopropanecarboxylic acid methyl ester

(1R,3S)-3-Chlorocarbonyl-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester

diazomethane

(1R,4R,5S)-4-hydroxy-6,6-dimethyl-3-oxabicyclo[3.1.0]hexa-2-one

Refernces

• 1、 Farina, F.,Martin, M. V.,Soria, M. L.. "PSEUDOESTERES Y DERIVADOS XXXIII. SINTESIS DE COMPUESTOS CICLOPROPANICOS POR FOTOLISIS DE PIRAZOLINAS OBTENIDAS POR CICLOADICION 1,3-DIPOLAR A LA 5-METOXI-2(5H)-FURANONA". . p. 65 - 73. Retrieved 2007/10/02.
• 2、 Muljiani, Z.,Gadre, Smita,Joshi, Vijaya,Mitra, R. B.. "A SIMPLE PROCESS FOR THE SYNTHESIS OF METHYL (+/-)-CIS-3-FORMYL-2,2-DIMETHYL-1-CYCLOPROPANECARBOXYLATE". . p. 135 - 140. Retrieved 2007/10/02.