Ptilocaulin

Base Information

• Chemical Name: Ptilocaulin
• CAS No.: 78777-02-3
• Molecular Formula: C₁₅H₂₅N₃
• Molecular Weight: 247.384
• DSSTox Substance ID: DTXSID501000014
• Nikkaji Number: J755.750G
• Wikidata: Q82993362
• Metabolomics Workbench ID: 167753
• ChEMBL ID: CHEMBL454881
• Mol file: 78777-02-3.mol

Synonyms:isoptilocauline;ptilocaulin;ptilocaulin, (3aS-(3aalpha,5aalpha,8aalpha,8balpha))-isomer

Chemical Property of Ptilocaulin

Chemical Property:

• Vapor Pressure: 5.39E-06mmHg at 25°C
• Boiling Point: 380.6°C at 760 mmHg
• Flash Point: 184°C
• PSA: 50.41000
• Density: 1.28g/cm³
• LogP: 3.24790
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 247.204847810
• Heavy Atom Count: 18
• Complexity: 397

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC1=C2C3C(CCC3N=C(N2)N)CC1C
• Isomeric SMILES: CCCCC1=C2[C@@H]3[C@@H](CC[C@@H]3N=C(N2)N)C[C@@H]1C

Technology Process of Ptilocaulin

There total 11 articles about Ptilocaulin 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:

1-methoxybicyclo<3.2.2>non-6-en-2-one (53922-08-0,100692-90-8) → (+/-)-ptilocaulin (78777-02-3,86594-29-8,88154-76-1,88154-82-9,105930-25-4,105930-31-2,131100-65-7)

Guidance literature:

Multi-step reaction with 10 steps

1: potassium tert-butoxide / tetrahydrofuran / 96 h / Ambient temperature

2: 87 percent / tetrahydrofuran; hexane / 1 h / -100 - -80 °C

3: 89 percent / TsOH / benzene / 1.5 h / 80 °C

4: 64 percent / benzene / 3 h / Irradiation

5: 1.) lithium tri-sec-butylborohydride, 2.) aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, RT, 12 h, 2.) RT, 2 h

6: 99 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

7: 1.) borane-methyl sulfide, 2.) 3 M aq. NaOH, 30percent hydrogen peroxide / 1.) THF, 6 h, 0 deg C 2.) 50 deg C, 10 h

8: 97 percent / Collins reagent / CH₂Cl₂ / 0.08 h / Ambient temperature

9: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

10: benzene / 25 h / Heating

With 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; Collins oxidation agent; potassium tert-butylate; dihydrogen peroxide; L-Selectride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00251a004

Reference yield:

1-butyl-exo-8-methylbicyclo<3.2.2>non-6-en-2-one (103931-12-0) → (+/-)-ptilocaulin (78777-02-3,86594-29-8,88154-76-1,88154-82-9,105930-25-4,105930-31-2,131100-65-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 64 percent / benzene / 3 h / Irradiation

2: 1.) lithium tri-sec-butylborohydride, 2.) aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, RT, 12 h, 2.) RT, 2 h

3: 99 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

4: 1.) borane-methyl sulfide, 2.) 3 M aq. NaOH, 30percent hydrogen peroxide / 1.) THF, 6 h, 0 deg C 2.) 50 deg C, 10 h

5: 97 percent / Collins reagent / CH₂Cl₂ / 0.08 h / Ambient temperature

6: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

7: benzene / 25 h / Heating

With 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; Collins oxidation agent; potassium tert-butylate; dihydrogen peroxide; L-Selectride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00251a004

Reference yield:

4-butyl-exo-3-methylbicyclo<4.3.0>non-4-en-7-one (103931-13-1) → (+/-)-ptilocaulin (78777-02-3,86594-29-8,88154-76-1,88154-82-9,105930-25-4,105930-31-2,131100-65-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lithium tri-sec-butylborohydride, 2.) aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, RT, 12 h, 2.) RT, 2 h

2: 99 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

3: 1.) borane-methyl sulfide, 2.) 3 M aq. NaOH, 30percent hydrogen peroxide / 1.) THF, 6 h, 0 deg C 2.) 50 deg C, 10 h

4: 97 percent / Collins reagent / CH₂Cl₂ / 0.08 h / Ambient temperature

5: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

6: benzene / 25 h / Heating

With 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; Collins oxidation agent; potassium tert-butylate; dihydrogen peroxide; L-Selectride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/jo00251a004

upstream raw materials:

(6SR,7aSR)-5-butyl-6-methyl-1,2,5,6,7,7a-hexahydroinden-4-one

guanidine nitrate

endo-3-butyl-exo-4-methylbicyclo<4.3.0>non-1(9)-en-2-one

1-methoxybicyclo<3.2.2>non-6-en-2-one

Refernces

Total synthesis of (+)-ptilocaulin

10.1016/S0040-4039(00)97726-8

Morio Asaoka, Masahito Sakurai, and Hisashi Takei from the Department of Life Chemistry at the Tokyo Institute of Technology describe the first successful synthesis of (+)-ptilocaulin, a compound isolated from the Caribbean sponge Ptilocaulis aff. P. spiculifer, known for its antimicrobial and cytotoxic properties. The synthesis begins with (S)-(+)-5-trimethylsilyl-2-cyclohexenone (1), undergoing a series of reactions including 1,4-addition of a Grignard reagent, elimination of the trimethylsilyl group with CuCl2, further 1,4-addition with dimethylcuprate, alkylation with crotyl bromide, hydrogenation, and treatment with guanidine and dilute nitric acid. The final product, (+)-ptilocaulin nitrate, is obtained with a melting point of 182.5-184°C and an optical rotation of [a]D +74.1°, closely matching the literature values.

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