78008-36-3

Basic information

• Product Name: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde
• Synonyms: (R)-1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXALDEHYDE;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXYALDEHYDE;(R)-(+)-1,4-Dioxospiro(4,5)decane-2-carboxaldehyde;(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CABOXYALDEHYDE;1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE;(R)-(+)-2,2,CYCLOHEXYL-1,3-DIOXALANE-4-CARBOXALDEHYDE;(R)-1,4-Dioxaspiro[4
• CAS NO: 78008-36-3
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.21
• Product Categories: Small molecule;chiral;Aldehydes;Chiral Building Blocks;Organic Building Blocks
• Mol File: 78008-36-3.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 271.195°C at 760 mmHg
• Flash Point: 218 °F
• Appearance: /
• Density: 1.108 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(78008-36-3)
• EPA Substance Registry System: (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(78008-36-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 78008-36-3(Hazardous Substances Data)

Usage

Description

(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is a chiral organic compound featuring a spirocycle structure with a carboxaldehyde functional group. It is an important building block in the synthesis of various complex molecules and has found applications in the field of organic chemistry, particularly in asymmetric synthesis and the preparation of biologically active compounds.

Uses

Used in Organic Chemistry:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a key intermediate for the synthesis of complex organic molecules, particularly in asymmetric synthesis and the preparation of biologically active compounds.
Used in Proline-Catalyzed Diels Alder Reaction:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a reactant in the Proline-catalyzed Diels Alder reaction, which is a powerful method for constructing complex molecular frameworks with high stereoselectivity.
Used in Stereodivergent Synthesis of Carbahexofuranoses:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a reactant in the stereodivergent synthesis of carbahexofuranoses, employing a Wittig olefination-Claisen rearrangement protocol. This method allows for the preparation of a variety of carbasugars with different stereochemistries.
Used in Wittig Reactions:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a reactant in Wittig reactions, which are widely used for the synthesis of alkenes and other olefinic compounds with high stereoselectivity.
Used in Crotylation Reactions:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a reactant in crotylation reactions, which are important for the synthesis of various natural products and pharmaceutical compounds.
Used in Asymmetric Synthesis of Goniothalesdiol A:
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde is used as a key intermediate in the asymmetric synthesis of Goniothalesdiol A, a biologically active compound, via stereocontrolled allylation and base-catalyzed oxy-Michael addition.

InChI:InChI=1/C9H14O3/c10-6-8-7-11-9(12-8)4-2-1-3-5-9/h6,8H,1-5,7H2/t8-/m0/s1

Upstream product

• 76779-67-4 1,2,5,6-di-O-cyclohexylidene-D-mannitol 
• 95335-91-4 (S)-1,4-dioxaspiro<4.5>decane-2-methanol 
• 933-40-4 cycloxexanone dimethyl ketal 
• 69-65-8 mannitol 
• 108-94-1 cyclohexanone 
• 6614-52-4 5,6-O-cycloheyxlidene-(L)-ascorbic acid 
• 103959-91-7 (S)-2-(benzyloxy)-2-{(S)-1',4'-dioxaspiro[4.5]decan-2'-yl}ethan-1-ol 
• 881377-27-1 5,6-O-cyclohexylidene-gulono-1,4-lactone 
• 229639-21-8 3,4-O-cyclohexylidene-L-(S)-erythrulose 
• 102335-37-5 5-((2S)-1,4-dioxaspiro[4.5]dec-2-yl)(3S,4R,5S)-3,4-dihydroxy-3,4,5-trihydrofuran-2-one 
• 229639-27-4 (S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-ethane-1,2-diol 
• 99744-80-6 4,5-O-cyclohexylidene-L-arabinose dibenzyl dithioacetal 

Downstream Products

• 204512-01-6 (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 
• 204511-92-2 (S,S,R)-(+)-[4,5]-[O-Cyclohexylidene-3,4,5-trihydroxy-1-(2,6-di-tert-butyl-4-methoxy-1-phenoxycarbonyl)-1-pentylideneamino]-2-(1-ethyl-1-methoxypropyl)pyrrolidine 
• 245322-97-8 (2R,3R,4S)-1,2-O-cyclohexylidene-4-benzyloxymethyl-5-hexen-1,2,3-triol 
• 245322-99-0 (2R,3S,4SR)-1,2-O-cyclohexylidene-4-benzyloxymethyl-5-hexen-1,2,3-triol 
• 345892-01-5 (E)-(1R,2R)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 345891-97-6 (E)-(1R,2S)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 345891-96-5 (E)-(1S,2R)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 345891-99-8 (E)-(1S,2S)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 1292297-89-2 (S)-2-[3-(4-methoxybenzyloxy)propyl]-1,4-dioxaspiro[4.5]decane 
• 609-06-3 L-xylose 

Relevant articles and documents

Synthesis of enantiomeric diethyl (1R,2R)- and (1S,2R)-1,2,3- trihydroxypropylphosphonates

Addition of diethyl phosphite to 2,3-O-cyclohexylidene-D-glyceraldehyde catalyzed by triethylamine or fluorides led to ca. 35:65 mixtures of diethyl (1R,2R)- and (1S,2R)-2,3-O-cyclohexytidene-1,2,3-trihydroxypropylphosphonates (4a) and (4b). Application of lithium diethylphosphonate only slightly improved diastereoselectivity. Through chromatographic separation of 4a and 4b the protected trihydroxypropylphosphonates became available for the first time as pure enantiomers. The 1S configuration in the major diastereoisomer 4b was assigned on the basis of conformational and configurational analysis of 1,2-O-isopropylidene derivatives obtained from the title compounds.

An efficient synthesis of enantiomerically pure diethyl 2,3-dihydroxypropylphosphonate

A reliable method for the synthesis of the enantiomerically pure diethyl (R)-2,3-dihydroxypropylphosphonate from 1,2;5,6-di-O-cyclohexylidene-D-mannitol is elaborated.

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

A straightforward synthesis of (+)-trans-(4S,5R)- and (+)-cis-(4R,5R)-whisky lactones starting from D-(+)-mannitol has been reported here in fewer number of efficient steps compared to existing literature processes involving D-mannitol as the chiral pool starting material. Chiron approach directly translated chirality of D-mannitol to one of the two chiral centers in these target molecules. Toward this end, stereoisomerically pure trans- and cis-iodomethyl-γ-lactones were formed in the penultimate step. These two acted as versatile advanced common intermediates as they were also converted to the (+)-trans-(4S,5R)- and (+)-cis-(4R,5R)-cognac lactones, respectively. To the best of our knowledge, till date no synthesis of cognac lactones starting from D-mannitol has been reported. All these lactones are identified as the key aroma components of aged alcoholic beverages.

Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol

Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.