Ambroxdiol

Base Information

• Chemical Name: Ambroxdiol
• CAS No.: 10207-83-7
• Deprecated CAS: 1623004-48-7
• Molecular Formula: C₁₆H₃₀O₂
• Molecular Weight: 254.413
• UNII: X9X049Z30I,8R22IXW7BW
• Nikkaji Number: J367.478I
• Mol file: 10207-83-7.mol

Synonyms:13,14,15,16-tetranorlabdan-8,12-diol;sclareol glycol;sclareol glycol, (1R-(1alpha,2beta,4abeta,8aalpha))-isomer;sclareol glycol, (1S-(1alpha,2alpha,4aalpha,8abeta))-isomer;sklareol glycol;sklareol-glycol

Chemical Property of Ambroxdiol

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCC2(C1CCC(C2CCO)(C)O)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]1CC[C@@]([C@@H]2CCO)(C)O)(C)C

Technology Process of Ambroxdiol

There total 62 articles about Ambroxdiol 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: 85.0%

norisoambreinolide (564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5) → (+/-)-(1α,2β,4aβ,8aα)-decahydro-2-hydroxyl-2,5,5,8a-tetramethyl-1-naphthaleneethanol (10207-83-7,38419-75-9,41747-05-1,55881-96-4,64090-93-3,86023-44-1,86023-45-2,100679-84-3,105087-83-0,106035-74-9,106091-98-9,106091-99-0,122566-14-7,131831-64-6,131831-66-8,131831-67-9,131831-74-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Ambient temperature;

DOI:10.1016/S0040-4039(00)79879-0

Reference yield:

(+/-)-8-oxo-12-nordriman-11-acid methyl ester (59684-77-4,65794-68-5,115304-46-6,131831-72-6,133102-26-8,49749-46-4,141317-75-1) → (+/-)-(1α,2β,4aβ,8aα)-decahydro-2-hydroxyl-2,5,5,8a-tetramethyl-1-naphthaleneethanol (10207-83-7,38419-75-9,41747-05-1,55881-96-4,64090-93-3,86023-44-1,86023-45-2,100679-84-3,105087-83-0,106035-74-9,106091-98-9,106091-99-0,122566-14-7,131831-64-6,131831-66-8,131831-67-9,131831-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 20 °C

2: 62 percent / xylene / 3.5 h / Heating

3: 70 percent / CaCl₂*2H₂O / dimethylsulfoxide / 1.25 h / Heating

4: 98 percent / diethyl ether / 0.5 h / Heating

5: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -20 - -30 deg C, 2.) MeOH, -60 deg C

With sodium tetrahydroborate; sodium hydride; ozone; calcium chloride; In diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; xylene;

DOI:10.1002/hlca.19890720517

Reference yield:

rac-11-methanesulfonyloxy-12-nor-driman-8β-ol (65754-94-1,133132-76-0,136869-67-5) → (+/-)-(1α,2β,4aβ,8aα)-decahydro-2-hydroxyl-2,5,5,8a-tetramethyl-1-naphthaleneethanol (10207-83-7,38419-75-9,41747-05-1,55881-96-4,64090-93-3,86023-44-1,86023-45-2,100679-84-3,105087-83-0,106035-74-9,106091-98-9,106091-99-0,122566-14-7,131831-64-6,131831-66-8,131831-67-9,131831-74-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / PCC, NaOAc / CH₂Cl₂ / Ambient temperature

2: 80 percent / methanol; benzene / Ambient temperature

3: 72 percent / NH₄Cl / dimethylformamide; H₂O / Ambient temperature

4: 83 percent / KOH / methanol; H₂O / Heating

5: tetrahydrofuran; diethyl ether / -60 deg C to room temperature

6: TsOH / toluene / Heating

7: 85 percent / LiAlH₄ / diethyl ether / Ambient temperature

With potassium hydroxide; lithium aluminium tetrahydride; sodium acetate; ammonium chloride; pyridinium chlorochromate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(00)79879-0

upstream raw materials:

trans-syn-cis norambreinolide

(+/-)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-2t-enoic acid

4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3ξ-enoic acid ethyl ester

(+/-)-4-methyl-6-(2,6,6-trimethyl-cyclohex-2-enyl)-hex-3ξ-enoic acid ethyl ester

Downstream raw materials:

(±)-ambrox

(+/-)-5β,8α,9β-Ambrox

(+/-)-5β-Ambrox

(3aRS,5aSR,9aRS,9bSR)-dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan

Refernces

• 1、 Urones,Basabe,Marcos,Gonzalez,Jimenez,Sexmero,Lithgow. "Ambergris compounds from labdanolic acid". . p. 9991 - 9998. Retrieved 2007/10/02.
• 2、 Escher, Sina,Giersch, Wolfgang,Niclass, Yvan,Bernardinelli, Gerald,Ohloff, Guenther. "Configuration-Odor Relationship in 5β-Ambrox". . p. 1935 - 1947. Retrieved 2007/10/02.