(R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde

Base Information

• Chemical Name: (R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde
• CAS No.: 78008-36-3
• Molecular Formula: C9H14 O3
• Molecular Weight: 170.208
• Hs Code.: 2932999099
• European Community (EC) Number: 623-032-2
• DSSTox Substance ID: DTXSID40445991
• Nikkaji Number: J639.849I
• Wikidata: Q72472712
• Mol file: 78008-36-3.mol

Synonyms:78008-36-3;(R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde;(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde;(R)-1,4-Dioxaspiro[4.5]decane-2-carboxaldehyde;(2R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde;(3R)-1,4-dioxaspiro[4.5]decane-3-carbaldehyde;(R)-1,4-dioxaspiro[4.5]decane;(R)-2,3-Cyclohexylideneglyceraldehyde;A9843;1,4-Dioxaspiro[4.5]decane-2-carboxaldehyde, (2R)-;SCHEMBL2657636;DTXSID40445991;FFGZPNNLXMQFMO-QMMMGPOBSA-N;AMY13396;MFCD03093997;AKOS015855462;AKOS015911361;CS-W006985;DS-12919;D5511;1,4-Dioxaspiro[4.5]decane-2beta-carbaldehyde;O10155;J-502130

Chemical Property of (R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Boiling Point: 271.195°C at 760 mmHg
• Flash Point: 218 ºF
• PSA: 35.53000
• Density: 1.108
• LogP: 1.26110
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(CC1)OCC(O2)C=O
• Isomeric SMILES: C1CCC2(CC1)OC[C@@H](O2)C=O
• Uses: Reactant for:Proline-catalyzed Diels Alder reactionStereodivergent synthesis of carbahexofuranoses employing a Wittig olefination-Claisen rearrangement protocolWittig reactionsCrotylation reactionsAsymmetric synthesis of Goniothalesdiol A via stereocontrolled allylation and base-catalyzed oxy-Michael addition

Technology Process of (R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde

There total 24 articles about (R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde 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%

1,2,5,6-di-O-cyclohexylidene-D-mannitol (76779-67-4) → (R)-2,3-cyclohexylideneglyceraldehyde (78008-36-3)

Guidance literature:

With sodium periodate; In water; ethyl acetate; at 35 ℃; for 3h;

DOI:10.3390/molecules24244588

Reference yield: 95.0%

mannitol (69-65-8) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (R)-2,3-cyclohexylideneglyceraldehyde (78008-36-3)

Guidance literature:

mannitol; cyclohexanone; With boron trifluoride diethyl etherate; orthoformic acid triethyl ester; In dimethyl sulfoxide; at 20 ℃; for 12h;

With sodium periodate; In water; acetonitrile; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.carres.2021.108452

Reference yield: 92.0%

5-((2S)-1,4-dioxaspiro[4.5]dec-2-yl)(3S,4R,5S)-3,4-dihydroxy-3,4,5-trihydrofuran-2-one (102335-37-5) → (S)-cyclohexylidene glyceraldehyde (78008-36-3,92822-62-3,99744-77-1)

Guidance literature:

With potassium metaperiodate; potassium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 8h;

DOI:10.1021/jo050807f

upstream raw materials:

1,2,5,6-di-O-cyclohexylidene-D-mannitol

(S)-1,4-dioxaspiro<4.5>decane-2-methanol

cycloxexanone dimethyl ketal

mannitol

Downstream raw materials:

(2R)-2-[(1R)-1-(benzyloxy)prop-2-enyl]-1,4-dioxaspiro[4.5]decane

(2R,3R,4S)-1,2-O-cyclohexylidene-4-benzyloxymethyl-5-hexen-1,2,3-triol

(2R,3S,4SR)-1,2-O-cyclohexylidene-4-benzyloxymethyl-5-hexen-1,2,3-triol

(S)-5-(R)-1,4-Dioxa-spiro[4.5]dec-2-yl-3-[(E)-(S)-2-(1-ethyl-1-methoxy-propyl)-pyrrolidin-1-ylimino]-dihydro-furan-2-one

Refernces

• 1、 Caruso, Lucia,Puglisi, Alessandra,Gillon, Emmerance,Benaglia, Maurizio. "Organocatalytic Michael addition to (D)-mannitol-derived enantiopure nitroalkenes: A valuable strategy for the synthesis of densely functionalized chiral molecules". . . Retrieved 2019.
• 2、 Chakraborty, Ipsita,Chatterjee, Sandip,Manna, Avrajit,Bhaumik, Tanurima. "Confirmation of the stereochemistry of two naturally occurring epimeric phenylpropanoids via synthesis: Elucidation of hitherto unknown full stereostructures". . p. 1597 - 1599. Retrieved 2019.
• 3、 Manna, Avrajit,Chakraborty, Ipsita,Chatterjee, Sandip,Bhaumik, Tanurima. "A general and concise stereodivergent chiral pool approach toward trans-(4S,5R)- and cis-(4R,5R)-5-alkyl-4-methyl-γ-butyrolactones: Syntheses of (+)-trans- and (+)-cis-whisky and cognac lactones from D-(+)-mannitol". . . Retrieved 2021/10/12.