15507-06-9

Basic information

• Product Name: rel-(1α*,4α*)-Bicyclo[2.2.1]hepta-5-ene-2β*-methanol
• Synonyms: endo-5-Norbornene-2-methanol
• CAS NO: 15507-06-9
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18
• Mol File: 15507-06-9.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 97-98 °C(Press: 20 Torr)
• Appearance: /
• Density: 1.0150 g/cm3
• PKA: 14.92±0.10(Predicted)
• CAS DataBase Reference: rel-(1α*,4α*)-Bicyclo[2.2.1]hepta-5-ene-2β*-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: rel-(1α*,4α*)-Bicyclo[2.2.1]hepta-5-ene-2β*-methanol(15507-06-9)
• EPA Substance Registry System: rel-(1α*,4α*)-Bicyclo[2.2.1]hepta-5-ene-2β*-methanol(15507-06-9)

Safety Data

• Hazardous Substances Data: 15507-06-9(Hazardous Substances Data)

Upstream product

• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 120-74-1 endo-norbornenecarboxylic acid 
• 10138-32-6 ethyl bicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 4835-96-5 (-)-menthyl acrylate 
• 542-92-7 cyclopenta-1,3-diene 
• 96303-89-8 2-exo-acryloyloxy-N,N-dicyclohexylbornane-10-sulfonamide 
• 94594-91-9 acrylcamphorsultam 
• 89156-14-9 Acrylic acid (1S,2R,4R)-1-benzenesulfonylmethyl-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 96304-11-9 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(naphthalene-1-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-12-0 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(naphthalene-2-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-14-2 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(2,4,6-trimethyl-benzenesulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 96304-13-1 Acrylic acid (1S,2R,4R)-7,7-dimethyl-1-(phenanthrene-9-sulfonylmethyl)-bicyclo[2.2.1]hept-2-yl ester 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 85718-79-2 (1S,2S,4S)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (1R,2S,3R,4S)-3-(2,2-dimethyl-propoxy)-4,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester 

Downstream Products

• 95-09-0 5-chloromethylbicyclo[2,2,1]hep-2-ene 
• 75526-52-2 6-(phenylselanyl)hexahydro-2H-3,5-methanocyclopenta[b]furan 
• 135560-60-0 ((1R,2R,4R,5S,6S)-6-Bromo-5-phenylselanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 135560-59-7 ((1S,2S,4S,5S,6S)-5-Bromo-6-phenylselanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 79644-02-3 (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 85718-78-1 (endo-bicyclo[2.2.1]hept-5-ene-2-yl)methyl 3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 42070-73-5 Toluene-4-sulfonic acid (1S,2S,4S)-1-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 42070-73-5 Toluene-4-sulfonic acid (1S,2R,4S)-1-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 50626-34-1 5-(Tosyloxymethyl)bicyclo<2.2.1>hept-2-ene 
• 135560-61-1 ((1R,2R,4R,5S,6S)-6-Chloro-5-phenylsulfanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 135583-61-8 ((1S,2S,4S,5S,6S)-5-Chloro-6-phenylsulfanyl-bicyclo[2.2.1]hept-2-yl)-methanol 
• 110911-22-3 exo-phenylthio-3-oxatricyclo<4.2.0.0^4,8>nonane 
• 5240-72-2 exo-hydroxymethylnorbornane 
• 211758-35-9 bicyclo[2.2.1]hept-5-ene-2-methyl benzoate 

Relevant articles and documents

Method for preparing single-configuration C-2-position-monosubstituted norbornene derivative

The invention discloses a method for preparing a single-configuration C-2-position-monosubstituted norbornene derivative. The method comprises the following steps of: firstly, preparing exo-isomer enriched exo-isomer mixed 5-norbornene-2-carboxylic ester by taking commercial exo-isomer/endoisomer mixed 5-norbornene-2-carboxylic acid and large-steric-hindrance monohydric alcohol as raw materials; separating 5-norbornene-2-carboxylate with a single configuration through common column chromatography separation or fractionation; and finally, preparing the C-2-position-monosubstituted norbornene derivative with the single configuration from the separated 5-norbornene-2-carboxylate with the single configuration. The raw materials used in the invention are easy to obtain, the preparation process is simple, and the C-2-position-monosubstituted norbornene derivative with high purity (greater than 98%) and single configuration can be obtained.

Approach Matters: The Kinetics of Interfacial Inverse-Electron Demand Diels–Alder Reactions

Rapid and quantitative click functionalization of surfaces remains an interesting challenge in surface chemistry. In this regard, inverse electron demand Diels–Alder (IEDDA) reactions represent a promising metal-free candidate. Herein, we reveal quantitative surface functionalization within 15 min. Furthermore, we report the comprehensive effects of substrate stereochemistry, surrounding microenvironment and substrate order on the reaction kinetics as obtained by surface-bound mass spectrometry (DART-HRMS).

Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes

This work reports the development of highly potent and selective inhibitors of the β5c catalytic activity of human constitutive proteasomes. The work describes the design principles, large hydrophobic P3 residue and small hydrophobic P1 residue, that led to the synthesis of a panel of peptide epoxyketones; their evaluation and the selection of the most promising compounds for further analyses. Structure-activity relationships detail how in a logical order the β1c/i, β2c/i, and β5i activities became resistant to inhibition as compounds were diversified stepwise. The most effective compounds were obtained as a mixture of cis- and trans-biscyclohexyl isomers, and enantioselective synthesis resolved this issue. Studies on yeast proteasome structures complexed with some of the compounds provide a rationale for the potency and specificity. Substitution of the N-terminus in the most potent compound for a more soluble equivalent led to a cell-permeable molecule that selectively and efficiently blocks β5c in cells expressing both constitutive proteasomes and immunoproteasomes.