Enmein

Base Information

• Chemical Name: Enmein
• CAS No.: 3776-39-4
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423
• NSC Number: 526961
• DSSTox Substance ID: DTXSID20958812
• Nikkaji Number: J37.139D
• Wikidata: Q27104988
• Metabolomics Workbench ID: 135238
• ChEMBL ID: CHEMBL453801
• Mol file: 3776-39-4.mol

Synonyms:enmein

Chemical Property of Enmein

Chemical Property:

• Vapor Pressure: 1.91E-17mmHg at 25°C
• Melting Point: 274-276℃ (Decomposition) (ethanol )
• Boiling Point: 610.3°Cat760mmHg
• PKA: 12.66±0.60(Predicted)
• Flash Point: 220.1°C
• PSA: 93.06000
• Density: 1.37g/cm³
• LogP: 1.19540
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 362.17293854
• Heavy Atom Count: 26
• Complexity: 728

Purity/Quality:

≥98% ^*data from raw suppliers

Enmein ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CC2C3(C1C(OC3)O)C4CCC5CC4(C(=O)C5=C)C(=O)O2)O)C
• Isomeric SMILES: CC1([C@H](C[C@H]2[C@]3([C@@H]1[C@@H](OC3)O)[C@@H]4CC[C@@H]5C[C@]4(C(=O)C5=C)C(=O)O2)O)C

Technology Process of Enmein

There total 17 articles about Enmein 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: 71.0%

C24H36O6Si → enmein (3776-39-4)

Guidance literature:

With acetic acid; In water; at 110 ℃; for 3h; Sealed tube;

DOI:10.1002/anie.201803709

Reference yield:

C19H30O4Si → enmein (3776-39-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: palladium 10% on activated carbon; hydrogen / 5,5-dimethyl-1,3-cyclohexadiene / 72 h / 23 °C

2.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 - 23 °C

2.2: 3 h / 23 - 50 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

3.2: 0.42 h / -78 °C

4.1: sodium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium iodide / tetrahydrofuran / 15 h / -78 - 23 °C

4.2: 2 h / 23 °C

5.1: L-Selectride / tetrahydrofuran / 0.08 h / -78 °C

5.2: 3 h / 85 °C

6.1: sodium tetrahydroborate / methanol / 0.08 h / 0 °C

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 23 °C

8.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 0.08 h / 23 - 125 °C

9.1: hydrogenchloride / methanol; water / 1 h

10.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 23 °C

11.1: L-Selectride / tetrahydrofuran / 2 h / -78 °C

11.2: 6 h / 23 °C

12.1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h / 23 °C

12.2: 3 h / 23 °C

13.1: acetic acid / water / 3 h / 110 °C / Sealed tube

With hydrogenchloride; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; selenium(IV) oxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; tri-n-butyl-tin hydride; L-Selectride; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; toluene; mineral oil; 8.1: |Barton-McCombie Deoxygenation;

DOI:10.1002/anie.201803709

Reference yield:

C19H32O4Si → enmein (3776-39-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 - 23 °C

1.2: 3 h / 23 - 50 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 0.42 h / -78 °C

3.1: sodium hydride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium iodide / tetrahydrofuran / 15 h / -78 - 23 °C

3.2: 2 h / 23 °C

4.1: L-Selectride / tetrahydrofuran / 0.08 h / -78 °C

4.2: 3 h / 85 °C

5.1: sodium tetrahydroborate / methanol / 0.08 h / 0 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 23 °C

7.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 0.08 h / 23 - 125 °C

8.1: hydrogenchloride / methanol; water / 1 h

9.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 23 °C

10.1: L-Selectride / tetrahydrofuran / 2 h / -78 °C

10.2: 6 h / 23 °C

11.1: selenium(IV) oxide; tert.-butylhydroperoxide / dichloromethane / 2 h / 23 °C

11.2: 3 h / 23 °C

12.1: acetic acid / water / 3 h / 110 °C / Sealed tube

With hydrogenchloride; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; selenium(IV) oxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; L-Selectride; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; sodium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; toluene; mineral oil; 7.1: |Barton-McCombie Deoxygenation;

DOI:10.1002/anie.201803709

Refernces

• 1、 Pan, Saiyong,Chen, Sicong,Dong, Guangbin. "Divergent Total Syntheses of Enmein-Type Natural Products: (?)-Enmein, (?)-Isodocarpin, and (?)-Sculponin R". . p. 6333 - 6336. Retrieved 2018/04/30.