24192-01-6

Basic information

• Product Name: Dihydroyashabushiketol
• Synonyms: (S)-5-Hydroxy-1,7-diphenyl-3-heptanone;Dihydroyashabushiketol
• CAS NO: 24192-01-6
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 282.38
• Mol File: 24192-01-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: Dihydroyashabushiketol(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydroyashabushiketol(24192-01-6)
• EPA Substance Registry System: Dihydroyashabushiketol(24192-01-6)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 24192-01-6(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 2550-26-7 4-Phenyl-2-butanone 
• 30278-29-6 1,7-diphenylheptane-3,5-diol 
• 93559-15-0 1-(2-Phenethyl-[1,3]dioxolan-2-yl)-4-phenyl-butan-2-ol 
• 99482-47-0 5-Phenethyl-3-((E)-styryl)-4,5-dihydro-isoxazole 
• 4111-54-0 lithium diisopropyl amide 
• 352276-27-8 1-iodo-4-phenylbutan-2-one 
• 768-56-9 4-Phenylbut-1-ene 
• 115495-61-9 (5-Phenethyl-4,5-dihydro-isoxazol-3-ylmethyl)-phosphonic acid diethyl ester 
• 3277-89-2 phenethylmagnesium bromide 
• 72134-60-2 (2-Phenethyl-[1,3]dioxolan-2-yl)-acetaldehyde 
• 93559-08-1 (2-Phenethyl-[1,3]dioxolan-2-yl)-acetonitrile 
• 1036384-53-8 3,5-di-phenethyl-4,5-dihydroisoxazole 
• 93712-74-4 (5R)-trans-1,7-diphenyl-5-hydroxyhept-6-en-3-one 

Downstream Products

• 89762-89-0 5-hydroxy-1,7-diphenyl-3-heptanone-syn-O-benzyloxime 
• 89762-94-7 anti-5-benzyloxyimino-1,7-diphenyl-3-heptanol 
• 79559-59-4 1,7-diphenyl-4-heptene-3-one 
• 38572-30-4 1,7-bisphenylheptane-3,5-dione 
• 1036384-53-8 3,5-di-phenethyl-4,5-dihydroisoxazole 
• 107977-19-5 cis-4,6-diphenethyltetrahydro-2H-1,3-oxazin-2-one 
• 89762-99-2 syn-5-amino-3-hydroxy-1,7-diphenylheptane 
• 89762-99-2 anti-5-amino-1,7-diphenyl-3-heptanol 
• 100667-54-7 5-methoxy-1,7-diphenyl-3-heptanone 
• 1036384-70-9 4-(dimethyl-λ4-sulfanylidene)-1,7-diphenylheptane-3,5-dione 
• 38572-33-7 Benzoic acid (S)-3-oxo-1-phenethyl-5-phenyl-pentyl ester 

Relevant articles and documents

Ni/Chiral Sodium Carboxylate Dual Catalyzed Asymmetric O-Propargylation

A highly enantioselective O-propargylation catalyzed by combining a phosphine-nickel complex and an axially chiral sodium dicarboxylate has been developed. The transformation features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, offering an efficient approach to an array of enantioenriched O-propargyl hydroxylamines. Mechanistic studies support the presumed role of the chiral carboxylate as a counterion for nickel catalysis enabling the discovery of highly stereoselective transformations. The power of this reaction is illustrated by its application in the asymmetric total synthesis of potent firefly luciferase inhibitors and (S)-dihydroyashabushiketol.

Total synthesis of (5S)-dihydroyashabushiketol

Enantiomerically pure (+)-(5S)-dihydroyashabushiketol 1a was obtained by the 1,3-dipolar cycloaddition of a nitrile oxide, generated from oxime 3b, to N-acryloyl bornane[10,2]sultam (2R)-2 (67%, 85% de, then crystallization 81%, 99% de), followed by reduc

Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane

Boron enolates were in situ-generated reductively by treating various α-iodo ketones such as 2-iodo-1-phenylpropan-1-one, 2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived from α-iodo ketones and pinacolatoborane were successfully isolated by distillation, though the yields were rather moderate.