70600-49-6

Basic information

• Product Name: (E)-3-Nonen-1-yne
• Synonyms: (E)-3-Nonen-1-yne
• CAS NO: 70600-49-6
• Molecular Formula: C9H14
• Molecular Weight: 122.21
• Mol File: 70600-49-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-3-Nonen-1-yne(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-Nonen-1-yne(70600-49-6)
• EPA Substance Registry System: (E)-3-Nonen-1-yne(70600-49-6)

Safety Data

• Hazardous Substances Data: 70600-49-6(Hazardous Substances Data)

Upstream product

• 70600-64-5 trimethyl[(E)-non-3-en-1-ynyl]silane 
• 54542-97-1 (E)-1-heptenyldiisobutylaluminium 
• 2548-87-0 (E)-2-Octenal 
• 60595-37-1 (E)-1-iodohept-1-ene 
• 628-71-7 1-Heptyne 
• 42474-21-5 1,2-dibromoheptane 
• 89942-12-1 (E)/(Z)-1-bromo-1-heptene 
• 592-76-7 1-Heptene 
• 460-12-8 Butadiyne 
• 693-25-4 n-pentylmagnesium bromide 

Relevant articles and documents

Studies towards the total synthesis of Phostriecin

A synthetic approach toward the phostriecin, an antitumor natural product is described. The key features of the present synthesis are Wittig reaction, synthesis of homoallylic alcohol using Brown's protocol (alkoxyallylboration) and RCM for the creation of unsaturated lactone moiety of phostriecin.

Structure-Proving Syntheses of the Polyenoyltetramic Acids Pyranonigrin J and I

The polyenoyltetramic acids pyranonigrin J (3) and pyranonigrin I (4) had been isolated from Aspergillus niger. Their origins from and roles in biosynthesis as well as the S-configurations of their stereocenter had been deduced from expression experiments with modifications of the corresponding gene cluster. We corroborated this stereochemical assignment after executing the first total syntheses of both compounds because they had essentially the same specific rotations as their natural counterparts. Our syntheses used the β-ketothioester 18 as a conjunctive reagent. It was combined with the l-serine derivatives (S)-19 or (S)-21 (“Western building blocks”), respectively, through aminolyses. Stille couplings with the stannane 13 (“Eastern building block”) followed. The resulting β-ketoamides (S)-11 and (S)-12 underwent desilylative Lacey-Dieckmann cyclizations when exposed to 8 equiv. of Bu4NF. They rendered the polyenoyltetramic acids (S)-26 [acidolysis: → (S)-3] and (S)-4, respectively.

HIGHLY STEREO- AND REGIOSELECTIVE PALLADIUM-CATALIZED SYNTHESES OF (3E,5Z)-(3E,5E)-,AND (3Z,5E)-1,3,5-UNDECATRIENE

(3E,5Z)-1,3,5-Undecatriene (3) having 98.2percent stereoisomeric purity has been prepared by a new and expeditious route involving two selective Pd-catalyzed carbon-carbon bond forming reactions.The key step of this synthesis is a highly diastereoselective Pd-catalyzed cross-coupling reaction between 1-heptynylzinc chloride (11a) and a molar excess of (E)/(Z)-1,2-dibromoethylene (12). Another highly diastereoselective Pd-catalyzed reaction, which involves a cross-coupling between trimethylsilylethynylzinc chloride (15) and molar excesses of stereoisomeric mixtures of 1-bromo-1-alkenes (16), has been used to prepare (E)-1-trimethylsilyl-3-nonen-1-yne (10a), a key intermediate for the synthesis of (3E,5E)- and (3Z,5E)-undecatriene, (4) and (5).Compounds 3 and 4, isolated from the essential oil of Ferula galbaniflua, also occur together with compound 5 in the male attracting oils of seaweeds.These substances have odors highly appreciated in perfumery.