19398-89-1

Basic information

• Product Name: TRANS-4-DECENE
• Synonyms: TRANS-4-DECENE;(4E)-4-Decene;(E)-4-C10H20;(E)-4-decene;4-Decene, (E)-;t-4-Decene;trans-dec-4-ene;(E)-dec-4-ene
• CAS NO: 19398-89-1
• Molecular Formula: C₁₀H₂₀
• Molecular Weight: 140.27
• EINECS: 243-034-3
• Mol File: 19398-89-1.mol

Chemical Properties

• Boiling Point: 168-170 °C(lit.)
• Flash Point: 45 °C
• Appearance: /
• Density: 0.740 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.424
• CAS DataBase Reference: TRANS-4-DECENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-4-DECENE(19398-89-1)
• EPA Substance Registry System: TRANS-4-DECENE(19398-89-1)

Safety Data

• Statements: 10
• RIDADR: 1993
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 19398-89-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 154, 1980 DOI: 10.1021/jo01289a030

InChI:InChI=1/C10H20/c1-3-5-7-9-10-8-6-4-2/h7,9H,3-6,8,10H2,1-2H3/b9-7+

Upstream product

• 628-71-7 1-Heptyne 
• 1912-31-8 propyl methanesulfonate 
• 53248-87-6 cis-4-decene oxide 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 111-27-3 hexan-1-ol 
• 112-37-8 undecylenic acid 
• 546-67-8 lead(IV) tetraacetate 
• 71-43-2 benzene 
• 2384-86-3 4-decyne 
• 109-67-1 1-penten 
• 872-05-9 1-Decene 
• 19398-88-0 (Z)-dec-4-ene 
• 73881-10-4 (E)-1-bromo-2-hexene 
• 1942-46-7 5-decyne 

Downstream Products

• 592-99-4 4-octene 
• 29493-00-3 dodec-6-ene 
• 142-62-1 hexanoic acid 
• 107-92-6 butyric acid 

Relevant articles and documents

Catalytic, oxidant-free, direct olefination of alcohols using Wittig reagents

Reported here is the catalytic, acceptorless coupling of alcohols with in situ generated, non-stabilized phosphonium ylides to form olefins as major products. The reaction uses low catalyst loadings and does not require added oxidants. Hydrogenation of the product is minimized and the reaction leads to Z (aliphatic) or E (benzylic) stereospecificity.

Stabilization of long-chain intermediates in solution. octyl radicals and cations

The rearrangements of 1-octyl, 1-decyl and 1-tridecyl intermediates obtained from thermal lead(IV) acetate (LTA) decarboxylation of nonanoic, undecanoic and tetradecanoic acid were investigated experimentally through analysis and distribution of the products. The relationships between 1,5-, 1,6- and possibly existing 1,7-homolytic hydrogen transfer in 1-octyl-radical, as well as successive 1,2-hydride shift in corresponding cation have been computed via Monte-Carlo method. Taking into account that ratios of 1,5-/1,6-homolytic rearrangements in 1-octyl- and 1-tridecyl radical are approximately the same, the simulation shows very low involvement of 1,7-hydrogen rearrangement (1,5-/1,6-/1,7-hydrogen rearrangement = 85:31:1) in 1-octyl radical.

A selective Ru-catalyzed semireduction of alkynes to Z olefins under transfer-hydrogenation conditions

By using a readily available, air- and moisture-stable dihydrido-Ru complex, a variety of Z olefins are accessible under transfer-hydrogenation conditions with formic acid as the hydrogen source in excellent yields and Z/E selectivities. A discerning transformation: Z-Configured C=C bonds are stereoselectively formed from alkynes in the presence of a Ru catalyst with formic acid as the sole H2 source at room temperature (see scheme). A variety of functional groups are compatible with this novel procedure. Operational simplicity and the lack of overreduction products are characteristics for this unprecedented process.

TRANSITION METAL COMPLEXES

A transition metal complex which is a bis-arylimine pyridine MXn complex, comprising a bis-arylimine pyridine ligand having the formula (I), wherein R1-R5, R7-R9, R12 and R14 are each, independently, hydrogen, optionally substituted hydrocarbyl, an inert functional group, or any two of R1-R3 and R7-R9 vicinal to one another taken together may form a ring, and R6 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R7 or R4 to form a ring, R10 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R9 or R4 to form a ring, R11 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R12 or R5 to form a ring, R15 is hydrogen, optionally substituted hydrocarbyl, an inert functional group, or taken together with R14 or R5 to form a ring, provided that R13 and at least one of R12 and R14 are independently selected from optionally substituted C1-C30 alkyl, optionally substituted C4-C30 alkyloxy, halogen and optionally substituted C5-C20 aryl, or R13 taken together with R12 or R14 form a ring, or R12 taken together with R11 form a ring and R14 taken together with R15 form a ring, and provided that at least one of R12, R13 and R14 is optionally substituted C4-C30 alkyloxy; M is a transition metal atom in particular selected from Ti, V, Cr, Mn, Fe, Co, Ni, Pd, Rh, Ru, Mo, Nb, Zr, Hf, Ta, W, Re, Os, Ir or Pt; n matches the formal oxidation state of the transition metal atom M; and X is halide, optionally substituted hydrocarbyl, alkoxide, amide, or hydride. The transition metal complexes of the present invention, their complexes with non-coordinating anions and catalyst systems containing such complexes have good solubility in non-polar media and chemically inert non--polar solvents especially aromatic hydrocarbon solvents. The catalyst systems can be used for a wide range of (co-)oligomerization, polymerization and dimerization reactions.

METHOD FOR ISOMERIZING ORGANIC COMPOUND

PROBLEM TO BE SOLVED: To provide a method for isomerizing a compound bearing a hydrocarbon group having a carbon-carbon double bond which permits transfer of the carbon-carbon double bond of the compound without using a catalyst or an organic solvent. SOLUTION: The method for isomerizing the compound comprises transferring the position of the carbon-carbon double bond by causing the compound bearing the hydrocarbon group having the carbon-carbon double bond to non-catalytically react in a reaction medium in a high-temperature and high-pressure state. Thus, the isomer having the double bond transferred is obtained in a short time in one step by pressing the compound bearing the hydrocarbon group having the carbon-carbon double bond into high-temperature high-pressure water as a reaction site at a high speed. Neither waste nor wastewater to dispose of is discharged from the manufacturing processes.

Isomerization of 1-Decene by the Nickel Stearate-Ethylaluminum Chloride Catalytic System

The influence of the temperature, nature, and concentration of catalyst components on the conversion of 1-decene during its isomerization by the action of a Ni(OCOC17H35)2-(C2H 5)nAlCl3-n (n = 1.0, 1.5) catalyst system was studied. It was shown that the 1-decene conversion increased from 19 to 100 wt% within 60 min as the nickel stearate concentration was increased from 0.00016 to 0.002 mol/l. The conditions of the process that ensure attaining 100% conversion within 5 min were revealed. Under these conditions, a temperature change from 20 to 80°C had no substantial effect on the 1-decene isomerization process. An increase in the ethylaluminum sesquichloride concentration from 0.01 to 0.04 mol/l led to a fourfold growth in the 1-decene isomerization rate. It was found that ethylaluminum dichloride is a more effective cocatalyst than ethylaluminum sesquichloride. IR, 1H NMR, and 13C NMR measurements showed that 1-decene isomerizes in the presence of these catalytic systems into a mixture of all theoretically possible positional and geometrical isomers. Based on the results obtained, the nature of the active sites and the mechanism of 1-decene isomerization are discussed.

Multiple mechanistic pathways for zirconium-catalyzed carboalumination of alkynes. Requirements for cyclic carbometalation processes involving C-H activation

The reactions of internal and terminal alkynes with organoalanes containing Et, n-Pr, and i-Bu groups in the presence of Cp2ZrCl2 and MeZrCp2Cl were investigated with the goal of clarifying mechanistic details of some representative cases. Three fundamentally different processes, i.e., (i) C-M bond addition without C-H activation in the alkyl group, (ii) cyclic C-M bond addition via C-H activation, and (iii) hydrometalation, have been observed, and the courses of these reactions significantly depend on (i) the nature and number of alkyl groups in organoalanes, (ii) their amounts, and (iii) solvents. The reaction of alkynes with Et3Al in the presence of 0.1 equiv of Cp2ZrCl2 in nonpolar solvents, e.g., hexanes, proceeds via C-H activation to give the corresponding aluminacyclopentenes. Investigation of the reaction of 5-decyne with 1-3 equiv of Et3Al and 1 equiv of Cp2ZrCl2, which gave mono-, di-, or trideuterated (Z)-5-ethyl-5-decene as shown, together with the previously reported structural study on the reaction of Et3Al with Cp2ZrCl2 leading to the formation of well-characterized bimetallic species 9, 10, and 11, supports a catalytic cycle involving bimetallic species 10 and 18. In summary, this process requires a zirconocene derivative containing one Zr-bound Et group which is linked to Et3Al (but not to Et2AlCl) through a Cl bridge, i.e., 18, to produce 10 via β C-H activation. In sharp contrast, the reaction of Et2AlCl-Cp2ZrCl2 as well as of (n-Pr)2AlCl-Cp2ZrCl2 does not involve any C-H activation processes. It proceeds well in chlorinated hydrocarbon solvents, e.g., (CH2Cl)2, but it is extremely sluggish in nonpolar solvents, e.g., hexanes. The reaction may well involve direct C-Al bond addition to alkynes, as suggested earlier for Zr-catalyzed Me-Al bond addition to alkynes, but a few other alternatives cannot be ruled out on the basis of the currently available data. The reaction of alkynes with (n-Pr)3Al-Cp2ZrCl2 in nonpolar solvents proceeds partially via C-H activation and partially via hydrometalation. In contrast with the C-H activation process observed with Et3Al, that with (n-Pr)3Al is totally dominated by dimerization of alkynes to give aluminacyclopentadienes rather than aluminacyclopentenes, reflecting a previously established generalization that propene can be much more readily displaced from Zr by alkynes than ethylene. Hydrometalation is the exclusive process with (i-Bu)3Al-Cp2ZrCl2. This hydrometalation reaction, however, reveals a few interesting complications. Alkyl-substituted internal alkynes give double bond migrated products in addition to the expected hydrometalation products. With terminal alkynes the reaction produces the expected hydrometalation products and the 1,1-dimetalloalkanes in comparable yields. Various other related reactions involving other alkynes, e.g., PhC≡CPh, n-OctC≡CH, and PhC≡CH, and other reagents, e.g., Et3Al-MeZrCp2Cl, Et2AlCl-MeZrCp2Cl, and (n-Pr)3Al-MeZrCp2Cl, were also studied.

Selective Alkylation and Allylation of Allylic Halides by Tetraorganoidates: Regio- and Stereo-selective Synthesis of Rosefuran and Sesquirosefuran

Tetraalkylindanes regioselectively alkylate allylic bromides at the α-carbon.In this way, 1,5-dienes have been regio- and stereo-selectively synthesized by the allyl-allyl coupling of allylic bromides and allylic indates, including rosefuran 1 and sequirosefuran 3.

Metal/Ammonia Reduction of Ethers of 3-Decyn-1-ol: Effects of Structure and Conditions on Cleavage and Rearrangement

Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether.Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers.The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.

Application of Indium Ate Complexes to Synthetic Chemistry. Selective Conjugate Addition to Enones and Coupling with Allylic Halides

Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with α,β-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of hed-to-tail 1,5-dienes.