Cinnamosmolide

Base Information

• Chemical Name: Cinnamosmolide
• CAS No.: 23599-46-4
• Deprecated CAS: 25795-45-3
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375
• ChEMBL ID: CHEMBL402739
• DSSTox Substance ID: DTXSID00946419
• Metabolomics Workbench ID: 133692
• Nikkaji Number: J16.589A
• Wikidata: Q104399244
• Mol file: 23599-46-4.mol

Synonyms:cinnamosmolide

Chemical Property of Cinnamosmolide

Chemical Property:

• Vapor Pressure: 2.48E-10mmHg at 25°C
• Melting Point: 204 °C
• Refractive Index: 1.544
• Boiling Point: 458.4°Cat760mmHg
• PKA: 11.81±0.70(Predicted)
• Flash Point: 164.1°C
• PSA: 72.83000
• Density: 1.22g/cm³
• LogP: 1.97860
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 308.16237386
• Heavy Atom Count: 22
• Complexity: 563

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C=C2C(=O)OCC2(C3(C1C(CCC3)(C)C)C)O
• Isomeric SMILES: CC(=O)O[C@@H]1C=C2C(=O)OC[C@@]2([C@@]3([C@@H]1C(CCC3)(C)C)C)O

Technology Process of Cinnamosmolide

There total 21 articles about Cinnamosmolide 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:

6-oxo-7-drimen-11-ol acetate (110547-82-5) → (-)-cinnamosmolide (23599-46-4,73924-96-6,25795-45-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 74 percent / SeO₂ / dioxane / 16 h / Heating

2: 87 percent / p-TsOH / benzene / 6 h / Heating

3: 88 percent / DBU / benzene / 3 h / Heating

4: 98 percent / OsO₄, pyridine / 6 h / Ambient temperature

5: 20 percent / p-TsOH / 48 h / Ambient temperature

6: 80 percent / NaBH₄ / ethanol / 1) 0 deg C, 1 h, 2) 1 h, rt

7: 70 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / benzene / 24 h

8: pyridinium p-toluenesulphonate / acetone; H₂O / Ambient temperature

9: BaMnO₄/Al₂O₃/CuSO₄*5H₂O / benzene / 7 h / Ambient temperature

With pyridine; dmap; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; selenium(IV) oxide; barium permanganate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 1,4-dioxane; ethanol; water; acetone; benzene;

DOI:10.1016/S0040-4020(01)82328-0

Reference yield:

6-oxo-7,9-drimadien-12-al 12-ethylene acetal (137760-94-2) → (-)-cinnamosmolide (23599-46-4,73924-96-6,25795-45-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / OsO₄, pyridine / 6 h / Ambient temperature

2: 20 percent / p-TsOH / 48 h / Ambient temperature

3: 80 percent / NaBH₄ / ethanol / 1) 0 deg C, 1 h, 2) 1 h, rt

4: 70 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / benzene / 24 h

5: pyridinium p-toluenesulphonate / acetone; H₂O / Ambient temperature

6: BaMnO₄/Al₂O₃/CuSO₄*5H₂O / benzene / 7 h / Ambient temperature

With pyridine; dmap; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; barium permanganate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; copper(II) sulfate; triethylamine; In ethanol; water; acetone; benzene;

DOI:10.1016/S0040-4020(01)82328-0

Reference yield:

11-acetoxy-6-oxo-7-drimen-12-al (137760-91-9) → (-)-cinnamosmolide (23599-46-4,73924-96-6,25795-45-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / p-TsOH / benzene / 6 h / Heating

2: 88 percent / DBU / benzene / 3 h / Heating

3: 98 percent / OsO₄, pyridine / 6 h / Ambient temperature

4: 20 percent / p-TsOH / 48 h / Ambient temperature

5: 80 percent / NaBH₄ / ethanol / 1) 0 deg C, 1 h, 2) 1 h, rt

6: 70 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / benzene / 24 h

7: pyridinium p-toluenesulphonate / acetone; H₂O / Ambient temperature

8: BaMnO₄/Al₂O₃/CuSO₄*5H₂O / benzene / 7 h / Ambient temperature

With pyridine; dmap; aluminum oxide; sodium tetrahydroborate; osmium(VIII) oxide; barium permanganate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In ethanol; water; acetone; benzene;

DOI:10.1016/S0040-4020(01)82328-0

upstream raw materials:

Acetic acid (5R,9aS,9bS)-3,9b-dihydroxy-6,6,9a-trimethyl-1,3,5,5a,6,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-5-yl ester

6-oxo-7-drimen-11-ol acetate

6-oxo-7,9-drimadien-12-al 12-ethylene acetal

11-acetoxy-6-oxo-7-drimen-12-al

Refernces

• 1、 Naito, Takanobu,Nakata, Tadashi,Akita, Hiroyuki,Oishi, Takeshi. "SYNTHESES OF (+/-)-CINNAMODIAL AND (+/-)-CINNAMOSMOLIDE". . p. 445 - 446. Retrieved 2011/05/18.