625455-48-3

Basic information

• Product Name: (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol
• Synonyms: (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol
• CAS NO: 625455-48-3
• Molecular Weight: 188.269
• Mol File: 625455-48-3.mol

Chemical Properties

• CAS DataBase Reference: (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol(625455-48-3)
• EPA Substance Registry System: (1S,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol(625455-48-3)

Safety Data

• Hazardous Substances Data: 625455-48-3(Hazardous Substances Data)

Upstream product

• 99493-25-1 diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate) 
• 34271-30-2 (1S,2S)-2-phenylcyclopropane-1-carbaldehyde 
• 679429-87-9 1-((1S,2S)-2-Phenyl-cyclopropyl)-but-3-en-1-one 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 

Downstream Products

• 625455-50-7 Acrylic acid (R)-1-((1S,2S)-2-phenyl-cyclopropyl)-but-3-enyl ester 
• 625455-51-8 (6R,1'S,2'S)-6-(2'-phenylcyclopropyl)-5,6-dihydro-2H-pyran-2-one 
• 625455-49-4 (1R,1’S,2’S)-1-(2-phenylcyclopropyl)but-3-en-1-ol 
• 679429-87-9 1-((1S,2S)-2-Phenyl-cyclopropyl)-but-3-en-1-one 

Relevant articles and documents

Total synthesis of marine oxylipins constanolactone A and B

A short, high-yielding synthesis of the marine oxylipins constanolactone A and B was reported. Starting from cinnamyl alcohol (3), the cylopropyl lactone moiety 2 was obtained in 28% yield (11 steps). The second coupling partner, vinyl iodide 1, was isolated in 7 steps and 32% yield. Chromium mediated addition yielded the natural products as a 2:1 mixture (74%).

Synthesis and cytotoxic activities of goniothalamins and derivatives

Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.