rac Dihydro Samidin

Base Information

• Chemical Name: rac Dihydro Samidin
• CAS No.: 21311-66-0
• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.417
• DSSTox Substance ID: DTXSID40943821
• Wikidata: Q82920981
• Metabolomics Workbench ID: 123282
• ChEMBL ID: CHEMBL1302867
• Mol file: 21311-66-0.mol

Synonyms:dihydrosamidine;dimidin

Chemical Property of rac Dihydro Samidin

Chemical Property:

• PSA: 92.04000
• LogP: 3.52610
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 388.15220310
• Heavy Atom Count: 28
• Complexity: 666

Purity/Quality:

97% ^*data from raw suppliers

racDihydroSamidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)OC1C(C2=C(C=CC3=C2OC(=O)C=C3)OC1(C)C)OC(=O)C
• Uses: A derivative of Samidin (S110500). A derivative of Samidin (S110500). A potent vasodilatory agent isolated from Ammi visnaga. Used in the synthesis of (+/-)-Praeruptorin A.

Technology Process of rac Dihydro Samidin

There total 4 articles about rac Dihydro Samidin 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%

3-methylbutyric acid (503-74-2) + (+/-)-cis-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2) → (+/-)-dihydrosamidine (4992-73-8,6005-18-1,21311-66-0,107080-27-3,118492-25-4)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; Ambient temperature;

DOI:10.3987/R-1987-05-1239

Reference yield: 80.5%

(+/-)-trans-4'-acetylkhellactone (4955-21-9,35345-45-0,107080-28-4,112346-42-6,118492-19-6,118492-23-2) + isopentanoyl chloride (108-12-3) → (+/-)-trans-4'-acetyl-3'-isovalerylkhellactone (4992-73-8,6005-18-1,21311-66-0,107080-27-3,118492-25-4)

Guidance literature:

In benzene; Heating;

DOI:10.1248/cpb.43.859

Reference yield:

seseline (523-59-1) → (+/-)-dihydrosamidine (4992-73-8,6005-18-1,21311-66-0,107080-27-3,118492-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent Turnov_. / OsO₄, N-methylmorpholine-N-oxide dihydrate / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 72 h / Ambient temperature

2: 65 percent Turnov_. / BF₃*Et₂O / tetrahydrofuran / 2.8 h / Ambient temperature

3: 95 percent / 4-pyrrolidinopyridine, 1,3-dicyclohexylcarbodiimide (DCC) / Ambient temperature

With osmium(VIII) oxide; boron trifluoride diethyl etherate; 4-pyrrolidin-1-ylpyridine; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.3987/R-1987-05-1239

upstream raw materials:

3-methylbutyric acid

(+/-)-cis-4'-acetylkhellactone

seseline

(±)-cis-khellactone

Downstream raw materials:

3-Methyl-butyric acid 5-hydroxy-2,2-dimethyl-6-((E)-3-oxo-3-piperidin-1-yl-propenyl)-4-piperidin-1-yl-chroman-3-yl ester

3'-benzoyloxy-4'-piperidino-3,',4'-dihydroseselin

Acetic acid 5-hydroxy-2,2-dimethyl-6-((E)-3-oxo-3-piperidin-1-yl-propenyl)-4-piperidin-1-yl-chroman-3-yl ester

Benzoic acid 5-hydroxy-2,2-dimethyl-4-morpholin-4-yl-6-((E)-3-morpholin-4-yl-3-oxo-propenyl)-chroman-3-yl ester

Refernces

• 1、 Takeuchi,Kasama,Mayuzumi,Tamaru,Fukaya,Ohno,Tobinaga. "The antagonist effects of compounds derived from khellactone on platelet-activating factor". . p. 4221 - 4224. Retrieved 2007/10/02.