62555-05-9

Basic information

• Product Name: Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)-
• Synonyms: [[1-(3-iodo-2(E)-propenyl)-1-methylpentyl]oxy]trimethylsilane;dl-(E)-4-methyl-4-trimethylsilyloxy-1-iodo-1-octene;(+/-)-(E)-1-iodo-4-methyl-4-trimethylsilyloxy-1-octene;4-trimethylsilyloxy-4-methyl-l-iodo-l-octene;1-Iodo-4-methyl-4-trimethylsilyloxy-trans-1-octene;(dl)-(E)-4-methyl-4-trimethylsilyloxy-1-iodo-1-octene
• CAS NO: 62555-05-9
• Molecular Formula: C12H25IOSi
• Molecular Weight: 340.32
• Mol File: 62555-05-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)-(62555-05-9)
• EPA Substance Registry System: Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)-(62555-05-9)

Safety Data

• Hazardous Substances Data: 62555-05-9(Hazardous Substances Data)

Usage

General Description

"Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)-" is a complex organic chemical compound. It contains silane, which is a group that includes silicon and hydrogen. Silane, [[1-(3-iodo-2-propenyl)-1-methylpentyl]oxy]trimethyl-, (E)- also includes other chemical groups such as iodo, propenyl, methylpentyl, and trimethyl groups. The presence of these groups indicates that this substance is likely to be volatile and reactive. The (E)- prefix indicates the geometric configuration of the molecule, referring to the spatial arrangement of atomic groups around a double bond. The exact properties, uses, and hazards of this specific compound can vary greatly depending on its exact molecular structure and the conditions under which it is used or stored.

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

Downstream Products

• 81026-63-3 Enisoprost 

Relevant articles and documents

An efficient synthesis of the antisecretory prostaglandin enisoprost

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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.

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

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