62555-05-9

Usage

Uses

1. Used in Chemical Synthesis:
Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)is used as a reagent or intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the creation of new molecules with specific properties.
2. Used in Material Science:
In the field of material science, Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)is used as a precursor for the development of new materials with tailored properties. Its ability to form covalent bonds with other elements can lead to the creation of novel materials with improved characteristics, such as enhanced stability or reactivity.
3. Used in Pharmaceutical Industry:
Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)is used as a building block in the design and synthesis of new pharmaceutical compounds. Its unique chemical structure can contribute to the development of innovative drugs with improved efficacy and reduced side effects.
4. Used in Nanotechnology:
In nanotechnology, Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)is used as a component in the fabrication of nanoscale devices and materials. Its reactivity and ability to form stable bonds with other elements can be harnessed to create nanostructures with specific functions and properties.
5. Used in Surface Modification:
Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)is used as a surface modifier to alter the properties of various materials. Its ability to form covalent bonds with surfaces can lead to improved adhesion, corrosion resistance, or other desired characteristics. This application is particularly relevant in industries such as automotive, aerospace, and electronics.

Synthetic route

4-methyl-4-trimethylsilyloxyl-1-octyne (66792-28-7) → (1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9)

Conditions	Yield
With N-iodo-succinimide; Schwartz's reagent 1.) THF, RT, 20 min, 2.) RT; Multistep reaction;
With Schwartz's reagent; iodine 1) THF, 25 deg C, 30 min, 2) 0 deg C, 10 min, THF; Yield given. Multistep reaction;

1H-imidazole (288-32-4) + 1-iodo-4-hydroxy-4-methyl-trans-1-octene (62555-04-8) → (1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9)

Conditions	Yield
With chloro-trimethyl-silane In N-methyl-acetamide; hexane
With chloro-trimethyl-silane In N-methyl-acetamide; hexane
With chloro-trimethyl-silane In N-methyl-acetamide; hexane
With chloro-trimethyl-silane In N-methyl-acetamide; hexane

1H-imidazole (288-32-4) + 1-iodo-4-hydroxy-4-methyl-trans-octene (62555-04-8, 69647-56-9, 116052-01-8, 116052-02-9) → (1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9)

Conditions	Yield
With chloro-trimethyl-silane In N-methyl-acetamide; hexane

2-methyl-but-2-ene (513-35-9) → (1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium borohydrid; iodine / tetrahydrofuran 2: chloro-trimethyl-silane / N-methyl-acetamide; hexane View Scheme

4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone (61305-35-9, 61305-36-0, 61740-33-8, 56745-67-6) + (1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9) + Methyl 6-nitro-6-heptenoate (88462-11-7) → 7-[(1S,2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-4-methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-cyclopentyl]-6-nitro-heptanoic acid methyl ester (101642-17-5, 112354-59-3)

Conditions	Yield
With copper(l) iodide; tributylphosphine; tert.-butyl lithium Yield given. Multistep reaction;

(1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9) + methyl 7-(5-oxo-3-[(triethylsilyl)-oxy]-1-cyclopenten-1-yl)-heptanoate (112713-92-5) → 7-[(1R,2R,3R)-2-((E)-4-Methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-3-triethylsilanyloxy-cyclopentyl]-heptanoic acid methyl ester (84024-39-5, 138456-65-2)

Conditions	Yield
With n-butyllithium; methyllithium 1.) THF, -78 deg C, 1 h, 2.) -78 deg C; Yield given. Multistep reaction;

(1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9) + (+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-4(Z)-heptenoate (78908-11-9) → (Z)-7-[(1R,2R,3R)-2-((E)-4-Methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-3-triethylsilanyloxy-cyclopentyl]-hept-4-enoic acid methyl ester (78908-12-0, 78908-13-1, 78908-14-2, 78963-81-2, 84048-97-5, 138352-83-7)

Conditions	Yield
With n-butyllithium; methyllithium 1.) THF, -78 deg C, 1 h, 2.) -78 deg C; Yield given. Multistep reaction;

(1E)-(4R)-4-trimethylsilyloxy-4-methyl-1-iodo-1octene (62555-05-9) + (+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-4(Z)-heptenoate (78908-11-9) → Enisoprost (81026-63-3)

Conditions	Yield
Yield given. Multistep reaction;

Upstream product

• 288-32-4 1H-imidazole 
• 62555-04-8 1-iodo-4-hydroxy-4-methyl-trans-1-octene 
• 62555-04-8 1-iodo-4-hydroxy-4-methyl-trans-octene 
• 513-35-9 2-methyl-but-2-ene 
• 66792-28-7 4-methyl-4-trimethylsilyloxyl-1-octyne 

Downstream Products

• 81026-63-3 Enisoprost 

Relevant academic research and scientific papers

An Improved Procedure for the Synthesis of Prostaglandin Analogues

Hydrozirconation-iodination of a terminal acetylene followed by lithium-iodide exchange and finally dilithio cyanocuprate mediated conjugate addition to an appropriate cyclopentenone is reported as an efficient method for the synthesis of prostaglandin analogues.

1-Substituted-1-oxo-prostane-derivatives of the E, A and F series

The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E, F, or A series having on the terminal methylene carbon of the alpha chain, a substituent selected from the group consisting of: STR1 wherein R is C1 to C6 alkyl, and phenyl or phenyl substituted with one or more substituents selected from the group consisting of C1 -C4 alkyl, OR16, SR16, F, or Cl, and R16 is C1 to C6 alkyl.

1-Hydroxymethyl-1-1-oxo prostane derivatives of the E and F series

The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E, F, or A series having on the terminal methylene carbon of the alpha chain a substituent selected from the group consisting of: STR1 wherein R is an alkyl group and R15 is C1 -C4 alkyl, C1 -C4 alkoxy, di-C1 -C4 -alkylamino, and phenyl orphenyl substituted with one or more substituents selected from the group consisting of C1 -C4 alkyl, OR, SR, F, or Cl wherein R is as previously defined.

11-(2-Hydroxyethylthio) prostenoic acid E and F series derivatives

This disclosure describes certain 11-(2-hydroxyethylthio) prostenoic acid E and F series derivatives, and their intermediates, useful as bronchodilators and inflammatory medeator release inhibitors.

1-Hydroxymethyl-1-oxo-prostane derivatives of the E2 series

Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E2 series.

7-{3-Hydroxy-2β-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1α-yl}hept-5-cis-enoic acids and related compounds

7-{3-Hydroxy-2β-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1α-yl}hept-5-cis-enoic acids, displaying valuable pharmacological properties, e.g., gastric anti-secretory, are produced by the reaction of 7-(3-oxygenated-5-oxocyclopent-1-en-1-yl)hept-5-cis-enoic acid or ester with the appropriate organometallic reagent.

11-(2-Hydroxyethylthio)prostenoic acid E2 series derivatives

This disclosure describes certain 11-(2-hydroxyethylthio)-9-keto-prostenoic acid E series derivatives, and their intermediates, useful as bronchodilators and inflammatory medeator release inhibitors.

Novel 16 hydroxy 15-deoxy-5-cis-prostenoic acids and esters

This disclosure describes certain hydroxy substituted 15-deoxy-5-cis-prostenoic acids and esters useful as hypotensive agents, anti-ulcer agents, bronchodilators, anti-microbial agents, anticonvulsants, or as intermediates.