126191-23-9

Usage

Uses

Used in Pharmaceutical Industry:
(13Z)-4-Hydroxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-3,5,7(20),13,15,17(1),18-hepten-10-one is used as a pharmaceutical intermediate for the synthesis of various drugs and therapeutic agents. Its complex structure and reactive functional groups make it a promising candidate for the development of new medications with unique mechanisms of action.
Used in Chemical Research:
In the field of chemical research, (13Z)-4-Hydroxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-3,5,7(20),13,15,17(1),18-hepten-10-one serves as a subject for studying the synthesis and reactions of complex organic compounds. Its unique structure and functional groups provide opportunities for exploring novel chemical reactions and the development of innovative synthetic methods.
Used in Material Science:
(13Z)-4-Hydroxy-2,11-dioxatricyclo[13.2.2.13,7]icosa-3,5,7(20),13,15,17(1),18-hepten-10-one is utilized in material science for the development of new materials with specific properties. Its complex structure and functional groups can contribute to the creation of materials with unique characteristics, such as improved stability, reactivity, or selectivity in various applications.

Upstream product

• 134209-01-1 combretastatin D-2 methyl ether 
• 621-59-0 isovanillin 
• 1122-91-4 4-bromo-benzaldehyde 
• 1146133-42-7 (Z)-3-(4-bromophenyl)prop-2-en-1-ol 
• 84878-00-2 3-(4'-bromophenyl)-(Z)-propenoic acid methyl ester 
• 158469-53-5 3-<3-<4-(3-Hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>propionic acid 
• 158469-52-4 Ethyl (Z)-3-<3-<4-(3-hydroxy-1-(phenylsulfanyl)propyl)phenoxy>-4-methoxyphenyl>acrylate 
• 158469-54-6 4-Methoxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one 
• 158469-57-9 4-Hydroxy-14-(phenylsulfanyl)-2,11-dioxatricyclo<13.2.2.1^3,7>eicosa-1(18),3,5,7(20),1(19),16-hexaen-10-one 
• 1026324-32-2 Methyl 3-<4-(5-iodo-2-methoxyphenoxy)phenyl>-3-(phenylsulfanyl)propionate 
• 158469-51-3 3-<4-(5-Iodo-2-methoxyphenoxy)phenyl>-3-(phenylsulfanyl)propan-1-ol 
• 158469-50-2 Methyl (Z)-3-<4-(5-iodo-2-methoxyphenoxy)phenyl>acrylate 
• 158469-49-9 4-(5-Iodo-2-methoxyphenoxy)benzonitrile 

Downstream Products

• 1146133-52-9 8-bis(benzyl)phosphorylcombretastatin D-2 

Relevant academic research and scientific papers

Syntheses of Combretastatins D-1, D-2, and D-4 via Ring Contraction by Flash Vacuum Pyrolysis

We report the syntheses of combretastatins D-2 and D-4 as well as a formal synthesis of combretastatin D-1 by a conceptually new route harnessing a ring-contracting flash vacuum pyrolytic extrusion of sulfur dioxide from the respective 16-membered sulfone precursors. Via flash vacuum pyrolysis, even metaparacyclophanes as small and strained as the hitherto unknown oxa[1.5]metaparacyclophane could be prepared as a side product en route to combretastatin D-2 by synchronous extrusion of SO2 and CO2.

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

Total synthesis of combretastatins D

The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construct

Synthesis of (±)-combretastatin D-1 and combretastatin D-2

(±)-Combretastatin D-1 was synthesized in 16 steps by way of its congener, combretastatin D-2. In the key step, the strained 15-membered lactone ring was formed using high-dilution Mitsunobu conditions in 89% yield. Saturated seco acid 4 was a much better substrate for the cyclization reaction than the unsaturated seco acid 3.

Total Synthesis of Combretastatin D-2: Intramolecular Ullmann Macrocyclization Reaction

The total synthesis of combretastatin D-2, a cytotoxic constituent of Combretum caffrum (Combretaceae), is detailed and is based on the implementation of a key intramolecular Ullmann macrocyclization reaction for formation of the cyclic 15-membered caffra