CID 16396350

Base Information

• Chemical Name: CID 16396350
• CAS No.: 475-20-7
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• Hs Code.: 29021990
• European Community (EC) Number: 207-491-2
• Wikipedia: Longifolene
• Mol file: 475-20-7.mol

Synonyms:LONGIFOLENE;475-20-7;AKOS030490876;CID 16396350

Chemical Property of CID 16396350

Chemical Property:

• Appearance/Colour: Light-yellowish oil-shaped liquid
• Vapor Pressure: 0.0312mmHg at 25°C
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 252.2 °C at 760 mmHg
• Flash Point: 102.2 °C
• PSA: 0.00000
• Density: 0.93 g/cm³
• LogP: 4.41500
• Storage Temp.: 2-8°C
• Water Solubility.: 7.9mg/L at 24℃
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

Longifolene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCCC2(C3C1C(C2=C)CC3)C)C
• Isomeric SMILES: C[C@]12CCCC([C@@H]3C1CCC3C2=C)(C)C
• Uses: (+)-Longifolene is a tricyclic sesquiterpene, and the content in masson pine heavy turpentine is about 60%～78%. It has special chemical activity and can be used a raw material for synthetic resins, synthetic fragrances, flotation agents and organic synthesis.

Technology Process of CID 16396350

There total 36 articles about CID 16396350 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: 69.0%

sodium cyanide (143-33-9,25596-52-5) + [(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]methyl 4-methylbenzenesulfonate (4678-06-2,4678-07-3) → [(1R,2S,7R,8S,9R)-3,3,7-trimethyltricyclo[5.4.0.02,9]undec-8-yl]acetonitrile (943033-63-4) + longifolene (475-20-7)

Guidance literature:

sodium iodide; In dimethyl sulfoxide; at 90 ℃; for 24h;

DOI:10.1021/jm061204e

Reference yield: 66.0%

(+)-isolongiborneol (465-24-7,16846-28-9,18374-92-0,27551-75-3,51897-51-9) → longifolene (475-20-7)

Guidance literature:

With dmap; methanesulfonyl chloride; In pyridine; at 105 ℃; for 16h;

Reference yield: 56.0%

(-)-(1R)(2R)(7S)(8R)(9S)-3,3,7-Trimethyl-8-(acetoxymethyl)tricyclo<5.4.01,7.02,9>undecane (18367-70-9) → longifolene (475-20-7)

Guidance literature:

In benzene; at 525 ℃;

DOI:10.1021/jo00060a039

upstream raw materials:

Trimethyl-((1S,3aR,4S,8aS,9S)-4,8,8-trimethyl-decahydro-1,4-methano-azulen-9-ylmethyl)-ammonium; iodide

[(1R,2S,7S,8S,9S)-3,3,7-trimethyltricyclo[5.4.0.0^2,9]undec-8-yl]methyl 4-methylbenzenesulfonate

(+)-α-Longipinene

10-keto-longifolene

Downstream raw materials:

decahydro-1,5,5,8a-tetramethyl-1,2,4-methenoazulene

(1S,3aR,4S,8aS,9R)-decahydro-4,8,8-trimethyl-1,4-methanoazulen-9-carboxylic acid

(-)-longicamphenylone

(1S,3aR,4S,8aR,9S)-1,2,3,3a,4,5,6,7,8,8a-decahydro-4,8,8-trimethylspiro[1,4-methanoazulene-9,2'-oxirane]

Refernces

• 1、 Bichlmaier, Ingo,Kurkela, Mika,Joshi, Tanmaya,Siiskonen, Antti,Rüffer, Tobias,Lang, Heinrich,Suchanová, Bohumila,Vahermo, Mikko,Finel, Moshe,Yli-Kauhaluoma, Jari. "Isoform-selective inhibition of the human UDP-glucuronosyltransferase 2B7 by isolongifolol derivatives". . p. 2655 - 2664. Retrieved 2008/02/02.
• 2、 Shastri, Mayank H.,Dev, Sukh. "Studies in sesquiterpenes-lx reversion of longipinane to himachalane system: Revision of structure of isocentdarol". . p. 4905 - 4918. Retrieved 2007/10/02.