8-Isopropylidene-1,4-dioxa-spiro[4.5]decane

Base Information

• Chemical Name: 8-Isopropylidene-1,4-dioxa-spiro[4.5]decane
• CAS No.: 19620-35-0
• Molecular Formula: C11H18O2
• Molecular Weight: 182.263
• Hs Code.: 2932999099
• Mol file: 19620-35-0.mol

Synonyms:8-Isopropylidene-1,4-dioxa-spiro[4.5]decane

Chemical Property of 8-Isopropylidene-1,4-dioxa-spiro[4.5]decane

Chemical Property:

• Boiling Point: 256.4±40.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.01±0.1 g/cm3(Predicted)
• LogP: 2.63990

Purity/Quality:

98% ^*data from raw suppliers

8-(PROPAN-2-YLIDENE)-1,4-DIOXASPIRO[4.5]DECANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Isopropylidene-1,4-dioxa-spiro[4.5]decane

There total 6 articles about 8-Isopropylidene-1,4-dioxa-spiro[4.5]decane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

lithium dimethylcuprate (15681-48-8) + 4-(dibromomethylene)cyclohexanone ethylene ketal (175020-73-2) → 8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane (19620-35-0)

Guidance literature:

With methyl iodide; In diethyl ether; for 96h; Ambient temperature;

DOI:10.1021/jo951643d

Reference yield: 77.0%

cyclohexanedione monoethylene ketal (4746-97-8) + isopropyltriphenylphosphonium bromide (1530-33-2) → 8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane (19620-35-0)

Guidance literature:

isopropyltriphenylphosphonium bromide; With sodium hydride; In dimethyl sulfoxide; at 50 ℃;

cyclohexanedione monoethylene ketal; In dimethyl sulfoxide; at 50 ℃; for 16h;

DOI:10.1016/S0957-4166(00)00481-X

Reference yield: 66.7%

cyclohexanedione monoethylene ketal (4746-97-8) + isopropyltriphenylphosphonium iodide (24470-78-8) → 8-(propan-2-ylidene)-1,4-dioxaspiro[4.5]decane (19620-35-0)

Guidance literature:

isopropyltriphenylphosphonium iodide; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 50 ℃; for 0.75h; Inert atmosphere;

cyclohexanedione monoethylene ketal; In dimethyl sulfoxide; mineral oil; at 50 ℃; for 16.75h;

upstream raw materials:

lithium dimethylcuprate

4-(dibromomethylene)cyclohexanone ethylene ketal

cyclohexanedione monoethylene ketal

isopropyltriphenylphosphonium iodide

Downstream raw materials:

4-(propan-2-ylidene)cyclohexan-1-one

4-isopropyl-cyclohexanone

4-isopropyl-2-(pent-4-ynyl)cyclohexanone

(5S)-5-isopropyl-2-oxo-1-(pent-4-ynyl)cyclohexanecarboxylic acid methyl ester

Refernces

The Interaction of π orbitals with a carbocation over three σ bonds

10.1021/jo951643d

The study investigates the semi-π analogue of double hyperconjugation, known as "hyperconjugation/conjugation," in 4-isopropylidenecyclohexyl mesylate (4-OMs) and compares it with the saturated analogue, trans-4-isopropylcyclohexyl mesylate (5-OMs). The researchers found that the unsaturated substrate 4-OMs reacts only four times faster than the saturated substrate 5-OMs in 97% trifluoroethanol, indicating no significant through-bond interaction of the double bond with the reactive center. This is attributed to less than ideal overlap of the γ,δ π orbitals with the R, σ orbitals. However, when an electron-rich tin atom is attached to the 4-position, it provides a large rate enhancement and changes the mechanism to carbocation formation through double hyperconjugation. The study concludes that the π bond does not effectively stabilize positive charge through two stages of conjugation in the studied system, suggesting that the hyperconjugation/conjugation mode may not be a viable mechanism under the given conditions.