Hirsutene

Base Information

• Chemical Name: Hirsutene
• CAS No.: 59372-72-4
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• DSSTox Substance ID: DTXSID90974786
• Nikkaji Number: J12.395A
• Wikidata: Q76415675
• Metabolomics Workbench ID: 28429
• Mol file: 59372-72-4.mol

Synonyms:hirsutene

Chemical Property of Hirsutene

Chemical Property:

• PSA: 0.00000
• LogP: 4.41500
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2CC3CCC(=C)C3(C2C1)C)C
• Isomeric SMILES: C[C@]12[C@H](CCC1=C)C[C@@H]3[C@H]2CC(C3)(C)C

Technology Process of Hirsutene

There total 24 articles about Hirsutene 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: 80.0%

(1R,2S,6R,8S)-2,10,10-trimethyl-cis-anti-cis-tricyclo<6.3.0.02,6>-3-undecanone (96844-05-2) + Methylenetriphenylphosphorane (19493-09-5) → (+)-hirsutene (59372-72-4)

Guidance literature:

In toluene; for 2h; Heating;

DOI:10.1021/ja00299a061

Reference yield:

(1R,2S,6R,8S)-2,10,10-trimethyl-cis-anti-cis-tricyclo<6.3.0.02,6>-3-undecanone (96844-05-2) + Methyltriphenylphosphonium bromide (1779-49-3) → (+)-hirsutene (59372-72-4)

Guidance literature:

With sodium tert-pentoxide; Yield given. Multistep reaction; 1.) toluene, 25 deg C, 1 h, 2.) reflux, 3 h;

DOI:10.1021/jo00238a007

Reference yield:

3-bromo-2,2-dimethyl-propan-1-ol (40894-00-6) → (+)-hirsutene (59372-72-4)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N, DMAP / CH₂Cl₂

2: 1.) Li, CuI*Me₂S / 1.) RT; ether; 2.) ether, -30 deg C, 1 h

3: n-Bu₄NF / tetrahydrofuran / 15 h / Ambient temperature

4: pyridine / 20 h / Ambient temperature

5: NaH / 1,2-dimethoxy-ethane / 7 h / Heating

6: 95 percent / NaBH₄ / methanol / 0.5 h / -20 °C

7: 93 percent / Et₃N / diethyl ether

8: 72 percent / LiEt₃BH / toluene / 18 h / 90 °C

9: 90 percent / TsOH / tetrahydrofuran; methanol; H₂O / 1 h / Ambient temperature

10: 80 percent / toluene / 2 h / Heating

With pyridine; dmap; sodium tetrahydroborate; copper(I) iodide dimethyl sulfide complex; tetrabutyl ammonium fluoride; lithium; sodium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/ja00299a061

upstream raw materials:

(1R,2S,6R,8S)-2,10,10-trimethyl-cis-anti-cis-tricyclo<6.3.0.0^2,6>-3-undecanone

Methyltriphenylphosphonium bromide

Methylenetriphenylphosphorane

3-bromo-2,2-dimethyl-propan-1-ol

Refernces

Tandem Radical Approach to Linear Condensed Cyclopentanoids. Total Synthesis of (+/-)-Hirsutene

10.1021/ja00291a077

The study focuses on the development of a novel synthetic strategy for the total synthesis of (f)-hirsutene, a member of the hirsutane family, using a tandem radical cyclization approach. The researchers employed several key chemicals in their synthesis. Vinyl lactone 2 was used as a starting material, which was converted to iodide 3 through a series of reactions involving organolithium reagents and acid hydrolysis. The crucial step involved treating iodide 3 with tri-n-butyltin hydride, catalyzed by AIBN, to generate the transient radical 4, which underwent two successive hex-5-enyl-like radical cyclizations and a hydrogen atom abstraction to produce hirsutene (1) in a single step. The study demonstrated the potential of this tandem radical cyclization method for synthesizing linear condensed cyclopentanoids, with plans to extend this approach to more complex hirsutanoids and related capnellenes.