822-93-5

Basic information

• Product Name: 1,1-DICYCLOPROPYLETHYLENE
• Synonyms: 1,1-DICYCLOPROPYLETHYLENE;1,1'-vinylidenebiscyclopropane;1,1-Dicyclopropylethene;1-cyclopropylethenylcyclopropane;1-cyclopropylvinylcyclopropane
• CAS NO: 822-93-5
• Molecular Formula: C₈H₁₂
• Molecular Weight: 108.18
• EINECS: 212-508-1
• Mol File: 822-93-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,1-DICYCLOPROPYLETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DICYCLOPROPYLETHYLENE(822-93-5)
• EPA Substance Registry System: 1,1-DICYCLOPROPYLETHYLENE(822-93-5)

Safety Data

• Hazardous Substances Data: 822-93-5(Hazardous Substances Data)

Usage

Synthesis

Methyltriphenylphosphonium bromide (11.6 g, 32.4 mmoles) was weighed into a dry, 250 mL three neck, round bottom flask, and 50 mL of dry THF (distilled from Na/benzophenone) was cannulated into the reaction vessel. A positive pressure of argon was maintained throughout the reaction. The suspension was cooled to 0-5 ℃, and n-butyllithium, 2.5 M in hexane (14.0 mL, 32.4 mmoles) added dropwise from an addition funnel to the well-stirred solution. A yellow color developed upon addition of the base, indicative of formation of the Wittig reagent.Dicyclopropyl ketone (1) (3.5 mL, 32.4 mmoles), cooled to O℃, a bottle with vacuum distilled dicyclopropyl ketone was kept in ice-water bath for 30 minutes, then (1) was added dropwise to the Wittig reagent. The color changed from yellow to off-white once the addition was complete. The mixture was allowed to warm slowly to room temperature. The reaction mixture was stirred overnight under a positive pressure of argon. After 24 hr, the reaction mixture was extracted successively with 25 mL of water and 25 mL of saturated NaCI solution. The organic layer was dried over anhydrous MgSO4. The solvent was removed by fractional distillation using a short Vigreux column, and the residue analyzed by gas chromatography (Hewlett Packard 5890, using a DB-5 column, FID detector, 30 m length, 0.53 mm id). The reaction mixture consisted of 1,1-dicyclopropylethylene (2) (80%), unreacted dicyclopropyl ketone (10%), and unidentified compounds (10%). Triphenylphosphine oxide (3) was the primary byproduct .

Upstream product

• 18895-50-6 dicyclopropylmethylcarbinol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1121-37-5 dicyclopropyl ketone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 79521-21-4 C₈H₁₁⁽²⁾H 
• 79521-26-9 1-methyl-1-cyclopropyl-3-lithiomethylenecyclopropane 
• 74-95-3 1,1-dibromomethane 
• 186581-53-3 diazomethane 
• 27567-82-4 bicyclopropylidene 

Downstream Products

• 123316-46-1 2-chloro-3,3-dicyclopropylcyclobutanone 
• 136847-54-6 3,3-Dicyclopropyl-1,2,4-trioxolan 
• 136847-60-4 C₁₁H₁₆O₂ 
• 136847-61-5 3,3,6,6-Tetracyclopropyl-1,2,4,5-tetroxan 
• 1121-37-5 dicyclopropyl ketone 
• 10027-72-2 methoxymethyl hydroperoxide 
• 136847-59-1 3,3-Dicyclopropyl-1,2-dioxolan 
• 112641-89-1 2,2-dichloro-3,3-dicyclopropylcyclobutanone 
• 18895-50-6 dicyclopropylmethylcarbinol 
• 426265-83-0 C₆H₅(CH₃)2SiCH₂C(C₃H₅)CHCH₂CH₂BO₂C₂(CH₃)4 
• 426265-84-1 C₆H₅(CH₃)2SiCH₂C(CHSi(CH₃)2C₆H₅CH₂CH₂BO₂C₂(CH₃)4)CHCH₂CH₂BO₂C₂(CH₃)4 
• 1421271-11-5 N-(2,2-dicyclopropylethylidene)-4-methylbenzenesulfonamide 
• 83735-98-2 2-phenyl-3-phenylcarbamoyl-5,5-dicyclopropylisoxazolidine 
• 54159-42-1 1,1-Dicyclopropyl-2,2-diphenylcyclopropane 

Relevant articles and documents

Visible light-mediated intermolecular [2 + 2] photocycloaddition of 1-aryl-2-nitroethenes and olefins

Despite the importance of cyclobutanes there are not many direct [2 + 2] photocycloaddition reactions which can be performed with visible light in the absence of a catalyst. A notable exception is the reaction of 1-aryl-2-nitroethenes and olefins which can be performed at a wavelength of λ = 419 nm or λ = 424 nm in CH2Cl2 as the solvent. In the present study, a total of 15 1-aryl-2-nitroethenes were found to undergo a [2 + 2] photocycloaddition with 2,3-dimethyl-2-butene (28-86% yield) and a set of 12 olefins was studied in their photocycloaddition to 1-phenyl-2-nitroethene (37-88% yield). All mechanistic results are in agreement with a triplet reaction pathway and with the intermediacy of a 1,4-diradical.

(Azetidin-1-ylalkyl) lactams as tachykinin antagonists

The present invention provides compounds of formula (I) and the pharmaceutically acceptable salts thereof, wherein R is C3 -C7 cycloalkyl, aryl or C1 -C6 alkyl, said C1 -C6 alkyl, said C1 -C6 alkyl being optionally substituted by fluoro, COOH, --COO(C1 -C4 alkyl), C3 -C7 cycloalkyl, adamantyl, aryl or het1, and said C3 -C7 cycloalkyl being optionally substituted by 1 or 2 substituents each independently selected from C1 -C4 alkyl, C3 -C7 cycloalkyl, C1 -C4 alkoxy, hydroxy, fluoro, fluoro (C1 -C4) alkyl and fluoro (C1 -C4) Alkoxy; R1 is phenyl, naphthyl, thienyl, benzothienyl or indolyl, each optionally substituted by 1 or 2 substituents each independently selected from C1 -C4 alkyl, C1 -C4 alkoxy, halo and trifluormethyl; R2 is --CO2 H, --CONR3 R4, --CONR5 (C3 -C7 cycloalkyl), --NR5 (C2 -C5 alkanoyl), --NR3 R4, --NR5 CONR5 R6, (C3 -C7 cycloalkyl-C1 -C4 alkyl)R5 N--, --NR5 COCF3, --NR5 SO2 CF3, --NR5 (SO2 C1 -C4 alkyl), --NR5 SO2 NR5 R6, --NR5 (SO2 aryl), --N(aryl) (SO2 C1 -C4 alkyl), --OR5, --O(C3 -C7 cycloalkyl), --SO2 NR5 R6, het3 or a group of formulas: (a), (b), (c), (d), (e), (f), (g) or (h); X is C1 -C4 alkylene; X1 is a direct link or C1 -C6 alkylene; X2 is a direct link, CO, SO2, or NR5 CO; and m is 0, 1 or 2; together with intermediates used in the preparation of compositions containing and the use as tachykinin angatonists of such derivatives. STR1