(+)-ENDO-2-NORBORNEOL

Base Information

• Chemical Name: (+)-ENDO-2-NORBORNEOL
• CAS No.: 36779-79-0
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.172
• Mol file: 36779-79-0.mol

Synonyms:endo-(-)-2-Norborneol;(-)-endo-2-Norborneol;Bicyclo[2.2.1]heptan-2-ol,(1R-endo)-;

Chemical Property of (+)-ENDO-2-NORBORNEOL

Chemical Property:

• Melting Point: 148-150℃
• Boiling Point: 176.499 °C at 760 mmHg
• Flash Point: 74.376 °C
• PSA: 20.23000
• Density: 1.098 g/cm³
• LogP: 1.16730
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

(1R,2S,4S)-Bicyclo[2.2.1]heptan-2-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: endo-(-)-2-Norborneol is a useful intermediate for drugs and agrochemical.

Technology Process of (+)-ENDO-2-NORBORNEOL

There total 62 articles about (+)-ENDO-2-NORBORNEOL 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: 100.0%

(1S,4R)-bicyclo[2.2.1]heptan-2-one (497-38-1,2630-41-3) → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With [RuCl₂(triphenylphosphine)₂(1,2-diaminoethane)]; potassium tert-butylate; hydrogen; In isopropyl alcohol; tert-butyl alcohol; at 20 ℃; under 7240.26 Torr; Reagent/catalyst; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/op060063n

Reference yield: 93.0%

2-((1S,2S,4R)-Bicyclo[2.2.1]hept-2-yloxy)-tetrahydro-pyran → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With trichloroisocyanuric acid; In methanol; at 20 ℃; for 4h;

DOI:10.1081/SCC-200031053

Reference yield: 92.0%

exo-2,3-epoxynorbornane (278-74-0) → (1S,2S,4R)-2-norbornanol (497-36-9,497-37-0,1632-68-4,24325-44-8,29583-34-4,36779-79-0,60133-16-6,61277-90-5,61277-93-8)

Guidance literature:

With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide; In tetrahydrofuran; at 20 ℃; Electrochemical reaction;

DOI:10.1126/science.aav5606

upstream raw materials:

(+/-)-endo-2-norborneol

Isopropenyl acetate

(+/-)-endo-norborneol acetate

5-norbornene-2-ol

Downstream raw materials:

(1S,4R)-bicyclo[2.2.1]heptan-2-one

Norbornan-2-on

2,2-dimethoxybicyclo<2.2.1>heptane

(R)-exo-2-(5-bromo-2-methoxyphenoxy)bicyclo<2.2.1>heptane

Refernces

• 1、 Huang, Buwen,Elleraas, Jeff,Ewanicki, Jason,Sutton, Scott C.. "A short asymmetric synthesis of methyl 2-((1S,3R)-3-((tert-butyldiphenylsilyl)oxy)cyclopentyl)acetate from norbornene". supporting information. . Retrieved 2020/06/04.
• 2、 Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie. "Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration". supporting information. p. 4119 - 4129. Retrieved 2020/08/10.