1-Hydroxy-6,6-dimethyl-3-(5,5,5-trideuteriopentyl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid

Base Information

• Chemical Name: 1-Hydroxy-6,6-dimethyl-3-(5,5,5-trideuteriopentyl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
• CAS No.: 136844-96-7
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 347.427
• European Community (EC) Number: 802-953-5
• Mol file: 136844-96-7.mol

Synonyms:136844-96-7;AKOS015910229;6H-Dibenzo[b,d]pyran-9-carboxylicacid,6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-(pentyl-5,5,5-d3)-,(6ar,10ar)-rel-(9ci)

Chemical Property of 1-Hydroxy-6,6-dimethyl-3-(5,5,5-trideuteriopentyl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid

Chemical Property:

• Flash Point: 9℃
• PSA: 66.76000
• LogP: 4.80050
• Storage Temp.: 2-8°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 347.21758961
• Heavy Atom Count: 25
• Complexity: 524

Purity/Quality:

99% ^*data from raw suppliers

(±)-11-nor-9-Carboxy-Δ9-THC-D3 solution 1.0?mg/mLinmethanol,ampuleof1?mL,certifiedreferencematerial,Cerilliant? ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C(=O)O)O
• Isomeric SMILES: [2H]C([2H])([2H])CCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C(=O)O)O

Technology Process of 1-Hydroxy-6,6-dimethyl-3-(5,5,5-trideuteriopentyl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid

There total 4 articles about 1-Hydroxy-6,6-dimethyl-3-(5,5,5-trideuteriopentyl)-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid 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:

C35H49(2)H3N2SO4 (949595-96-4) + carbon dioxide (124-38-9,18923-20-1) → (6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-(5',5',5'-2H3-pentyl)-6H-dibenzo[b,d]pyran-9-carboxylic acid (130381-15-6,136844-96-7) + C21H25(2)H3O4

Guidance literature:

C₃₅H₄₉⁽²⁾H₃N₂SO₄; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at -78 - 0 ℃; for 1.5h;

carbon dioxide; In hexane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1016/j.tet.2007.06.006

Reference yield:

(6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(5',5',5'-2H3-pentyl)-9H-dibenzo[b,d]pyran-9-one (949595-91-9) → (6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-(5',5',5'-2H3-pentyl)-6H-dibenzo[b,d]pyran-9-carboxylic acid (130381-15-6,136844-96-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzene / 0.17 h / 40 - 42 °C

2.1: n-butyllithium; N,N,N',N'-tetramethylethylenediamine / hexane / 1.5 h / -78 - 0 °C

2.2: 137 mg / hexane / 0.17 h / 0 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; benzene; 2.1: Shapiro reaction;

DOI:10.1016/j.tet.2007.06.006

Reference yield:

C35H47(2)H5N2SO4 (949595-95-3) + carbon dioxide (124-38-9,18923-20-1) → (6aR,10aR)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-2H5-pentyl)-6H-dibenzo[b,d]pyran-9-carboxylic acid (949596-00-3,136844-96-7) + C21H23(2)H5O4

Guidance literature:

C₃₅H₄₇⁽²⁾H₅N₂SO₄; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at -78 - 0 ℃; for 1.5h;

carbon dioxide; In hexane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1016/j.tet.2007.06.006

upstream raw materials:

C₃₅H₄₇⁽²⁾H₅N₂SO₄

carbon dioxide

C₃₅H₄₉⁽²⁾H₃N₂SO₄

(6aR,10aR)-6,6a,7,8,10,10a-hexahydro-1-hydroxy-6,6-dimethyl-3-(4',4',5',5',5'-²H₅-pentyl)-9H-dibenzo[b,d]pyran-9-one

Refernces