1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)-

Base Information

• Chemical Name: 1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)-
• CAS No.: 67785-70-0
• Molecular Formula: C₁₃H₂₄O₃
• Molecular Weight: 228.332
• DSSTox Substance ID: DTXSID00886881
• Nikkaji Number: J429.620F
• Metabolomics Workbench ID: 48766
• Mol file: 67785-70-0.mol

Synonyms:67785-70-0;Menthone 1,3-glyceryl ketal;1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)-;8-methyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecan-3-ol;Menthone cyclic ketal with 1,2,3 propanetriol;1,5-Dioxaspiro(5.5)undecan-3-ol, 10-methyl-7-(1-methylethyl)-;SCHEMBL16884720;DTXSID00886881;CHEBI:174176;10-methyl-7-(propan-2-yl)-1,5-dioxaspiro[5.5]undecan-3-ol;3-Hydroxy-7-isopropyl-10-methyl-1,5-dioxaspiro[5.5]undecane;10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro[5.5]undecan-3-ol;10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro[5.5]undecan-3-ol, 9CI

Chemical Property of 1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)-

Chemical Property:

• Vapor Pressure: 6.49E-06mmHg at 25°C
• Refractive Index: 1.488
• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 158.7 °C
• PSA: 38.69000
• Density: 1.04 g/cm³
• LogP: 2.18260
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.17254462
• Heavy Atom Count: 16
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Menthone1,2-GlycerolKetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C2(C1)OCC(CO2)O)C(C)C
• Uses: Menthone 1,2-Glycerol Ketal is used as flavor enhancers in chewing gum. It is also a component of some antiperspirants and/or deodorants.

Technology Process of 1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)-

There total 3 articles about 1,5-Dioxaspiro[5.5]undecan-3-ol, 10-methyl-7-(1-methylethyl)- 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: 83.0%

(7S,10R)-10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro<5.5>undecan-3-one (138489-48-2) → (7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol (67785-70-0,138602-89-8,138604-09-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -80 - 25 ℃; for 3h; Product distribution; other reagent, other temperature, other time; stereoselectivity;

DOI:10.1021/jo00028a057

Reference yield: 8.0%

butyl magnesium bromide (693-04-9) + (7S,10R)-10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro<5.5>undecan-3-one (138489-48-2) → (7S,10R)-3-Butyl-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol (138489-45-9,138602-91-2) + (7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol (67785-70-0,138602-89-8,138604-09-8)

Guidance literature:

In diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo00028a057

Reference yield:

(7S,10R)-7-Isopropyl-10-methyl-3-methylene-1,5-dioxa-spiro[5.5]undecane (105857-49-6) → (7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol (67785-70-0,138602-89-8,138604-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) dimethyl sulfide / 1.) MeOH, -80 deg C, 2.) to 25 deg C, 3 h

2: 8 percent / diethyl ether / 1 h / 0 °C

With dimethylsulfide; ozone; In diethyl ether;

DOI:10.1021/jo00028a057

upstream raw materials:

(7S,10R)-10-Methyl-7-(1-methylethyl)-1,5-dioxaspiro<5.5>undecan-3-one

butyl magnesium bromide

(7S,10R)-7-Isopropyl-10-methyl-3-methylene-1,5-dioxa-spiro[5.5]undecane

Downstream raw materials:

2-[(1R,2S,5R)-1-((S)-2,3-Dihydroxy-propoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Refernces