58506-33-5

Basic information

• Product Name: (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL
• Synonyms: (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL
• CAS NO: 58506-33-5
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• Mol File: 58506-33-5.mol
• Article Data: 47

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL(58506-33-5)
• EPA Substance Registry System: (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-OL(58506-33-5)

Safety Data

• Hazardous Substances Data: 58506-33-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 2604, 1996 DOI: 10.1021/jo951923t

Upstream product

• 38447-05-1 (2E,4E)-methyl 5-phenylpenta-2,4-dienoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 1516-24-1 methyl 5-phenylpenta-2,4-dienoate 
• 1552-95-0 ethyl 5-phenyl-2,4-pentadienoate 
• 104-55-2 3-phenyl-propenal 
• 13466-40-5 5-phenylpenta-2,4-dienal 
• 60329-12-6 2-phenylmethylenecyclopropylmethanol 
• 112564-73-5 (2E)-1-phenyl-2,4-pentadiene-1-ol 
• 201230-67-3 2,4-pentanedienal 
• 103-26-4 Methyl cinnamate 
• 890022-08-9 ethyl (4E)-5-phenylpenta-2,4-dienoate 

Downstream Products

• 1794-46-3 ((1E,3E)-5-chloropenta-1,3-dien-1-yl)benzene 
• 109529-98-8 ((1E,3E)-5-bromopenta-1,3-dien-1-yl)benzene 
• 13466-40-5 5-phenylpenta-2,4-dienal 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 206873-03-2 N-(2E,4E)-5-phenylpenta-2,4-dienyltoluenesulfonamide 
• 944394-97-2 all-(E)-13-phenyltrideca-6,8,10,12-tetraen-1-ol 
• 392656-04-1 5-phenyl-trans,trans-2,4-pentadienyl α-diazoacetate 

Relevant articles and documents

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade

A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels–Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C?N and two C?C bonds, and two benzofused rings could be constructed concomitantly, which was made possible by distinct chemoselective control at both the 1,2-aryne and 2,3-aryne stages. Moreover, in-depth studies were carried out on the domino aryne precursors and controlling the diastereoselectivity.

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.