(+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione

Base Information

• Chemical Name: (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione
• CAS No.: 221054-70-2
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.229
• DSSTox Substance ID: DTXSID20431953
• Nikkaji Number: J1.176.685D
• Wikidata: Q76414624
• Mol file: 221054-70-2.mol

Synonyms:221054-70-2;(+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione;(5R)-5-ethyl-5-hydroxy-4,8-dihydro-1H-oxepino[3,4-c]pyridine-3,9-dione;(5R)-5-ETHYL-5-HYDROXY-1,4,5,8-TETRAHYDROOXEPINO[3,4-C]PYRIDINE-3,9-DIONE;SCHEMBL5532480;DTXSID20431953;RVBWWMADTISCJE-LLVKDONJSA-N;5beta-Hydroxy-5-ethyl-4,5-dihydrooxepino[3,4-c]pyridine-3,9(1H,8H)-dione;(5r)-5-ethyl-5-hydroxy-1,3,4,5,8,9-hexahydrooxepino[3,4-c]pyridin-3,9-dione

Chemical Property of (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione

Chemical Property:

• PSA: 79.65000
• LogP: 0.83170
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 410

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC(=O)OCC2=C1C=CNC2=O)O
• Isomeric SMILES: CC[C@]1(CC(=O)OCC2=C1C=CNC2=O)O

Technology Process of (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione

There total 28 articles about (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione 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%

(+)-5-ethyl-5-hydroxy-1-methoxy-5,9-dihydro-8-oxa-2-aza-benzocyclohepten-7(6H)-one (500726-35-2) → (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione (221054-70-2,387862-46-6)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; Heating;

DOI:10.1016/S0960-894X(99)00428-X

Reference yield: 54.0%

(R)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid (220998-02-7) → (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione (221054-70-2,387862-46-6)

Guidance literature:

With hydrogen bromide; In 1,2-dimethoxyethane; at 50 ℃; for 27h;

DOI:10.1021/jo060928v

Reference yield: 44.0%

(R)-3-hydroxy-3-(3-hydroxymethyl-2-methoxypyridin-4-yl)pentanoic acid (250347-75-2) → (+)-(5R)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione (221054-70-2,387862-46-6)

Guidance literature:

With hydrogen bromide; In 1,2-dimethoxyethane; at 20 - 50 ℃; for 18h;

DOI:10.1021/jo060928v

upstream raw materials:

(+)-5-ethyl-5-hydroxy-1-methoxy-5,9-dihydro-8-oxa-2-aza-benzocyclohepten-7(6H)-one

(R)-3-hydroxy-3-(3-hydroxymethyl-2-methoxypyridin-4-yl)pentanoic acid

(R)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid

1-(2-methoxypyridin-4-yl)propan-1-one

Downstream raw materials:

BN 80927

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