trans-2-Pinanol

Base Information

• Chemical Name: trans-2-Pinanol
• CAS No.: 35408-04-9
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.252
• UNII: Q3IVK90KUD
• DSSTox Substance ID: DTXSID8027583,DTXSID7091545
• Nikkaji Number: J415.403G
• Wikidata: Q81976234
• Mol file: 35408-04-9.mol

Synonyms:trans-2-Pinanol;cis-Pinene hydrate;4948-29-2;(1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol;cis-2-Pinanol;Pinan-2.beta.-ol;2-Pinanol, trans-;Q3IVK90KUD;NSC-2326;10 alpha-Pinan-2-ol;Bicyclo(3.1.1)heptan-2-ol, 2,6,6-trimethyl-, (1R,2R,5S)-rel-;DTXSID7091545;DTXSID8027583;2-PINANOL, TRANS-(+/-)-;35408-04-9

Chemical Property of trans-2-Pinanol

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 185

Purity/Quality:

(2R)-(-)-trans-2-Pinanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2CCC(C1C2)(C)O)C
• Isomeric SMILES: C[C@]1(CC[C@H]2C[C@@H]1C2(C)C)O
• Uses: (2R)-(-)-trans-2-Pinanol is a monoterpene and a component of several plant essential oils.

Technology Process of trans-2-Pinanol

There total 25 articles about trans-2-Pinanol 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:

(-)-α-pinene (7785-26-4,25766-18-1) → beta-pinene (18172-67-3,19902-08-0,25719-60-2) + 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (35408-04-9) + (1S)-(-)-cis-pinane (4755-33-3) + (1R,5R)-2(10),3-pinadiene (23733-90-6)

Guidance literature:

With NaPW₉O₃₄₂Pd₂Fe; hydrogen; oxygen; silica gel; In acetonitrile; at 35 ℃; for 1h; Further Variations:; Reagents; Product distribution;

DOI:10.1023/A:1025688908667

Reference yield:

beta-pinene (18172-67-3,19902-08-0,25719-60-2) → 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (35408-04-9) + (1S,2S,5S)-(-)-myrtanol (53369-17-8)

Guidance literature:

beta-pinene; With borane-ammonia complex; In tetrahydrofuran; at 90 ℃; for 1h;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

Reference yield:

nitrosyl acetate (5813-49-0) + 2αH-pinan-3α-ylamine (13293-47-5,17371-27-6,35117-55-6,35117-58-9,35117-61-4,35117-66-9,69460-11-3,69460-12-4,74281-72-4) → terpineol (98-55-5,2438-12-2) + 1,3,3-trimethylbicyclo<2.2.1>heptan-2-endo-yl acetate (4057-31-2,13851-11-1,56282-46-3,69651-95-2,76109-40-5,99341-77-2,111821-74-0) + terpinyl acetate (80-26-2) + pinan-2α-ol (473-54-1,4948-28-1,4948-29-2,18492-55-2,23516-36-1,25926-77-6,35408-04-9,35519-42-7,112574-21-7) + isobornyl acetate (76-49-3,125-12-2,5655-61-8,6626-35-3,17283-45-3,20347-65-3,28974-17-6,36386-52-4,71424-71-0,92618-89-8) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

In acetic acid; at 25 ℃;

upstream raw materials:

methyl magnesium iodide

(1R,5S)-(+)-nopinone

methylmagnesium bromide

(1R,2R,5R)-2,6,6-Trimethylbicyclo<3.1.1>hept-3-en-2-ol

Downstream raw materials:

4-methylisopropylbenzene

limonene.

(-)-α-pinene

(1S)-2-endo-chlorofenchane

Refernces

• 1、 -. "OPEN-FLASK HYDROBORATION AND THE USE THEREOF". Paragraph 0046; 0058; 0059. . Retrieved 2018/03/25.
• 2、 Sercheli, Ricardo,Ferreira, Alfredo L. B.,Baptistella, Lúcia H. B.,Schuchardt, Ulf. "Transition-Metal Catalyzed Autoxidation of cis- and trans-Pinane to a Mixture of Diastereoisomeric Pinanols". . p. 1361 - 1364. Retrieved 2007/10/03.