16369-17-8

Basic information

• Product Name: D/L-LEUCINOL
• Synonyms: D/L-LEUCINOL;Nsc64339
• CAS NO: 16369-17-8
• Molecular Formula: C₆H₁₅NO
• Molecular Weight: 117.19
• Mol File: 16369-17-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 44°C
• Boiling Point: 219.03°C (rough estimate)
• Flash Point: 90.6°C
• Appearance: /
• Density: 0.9173
• Refractive Index: 1.4444 (estimate)
• CAS DataBase Reference: D/L-LEUCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: D/L-LEUCINOL(16369-17-8)
• EPA Substance Registry System: D/L-LEUCINOL(16369-17-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43-36
• Safety Statements: 26-36-36/37
• Hazardous Substances Data: 16369-17-8(Hazardous Substances Data)

Usage

Description

D/L-Leucinol, also known as 2-amino-4-methylpentano, is an organic compound that belongs to the class of alpha-amino alcohols. It is a mixture of the D and L enantiomers of leucinol, an amino alcohol derived from the amino acid leucine. D/L-Leucinol has potential applications in the pharmaceutical and chemical industries due to its chiral nature and potential use as a building block in the synthesis of pharmaceuticals and other organic compounds. It is also being researched for its potential use as a chiral reagent in asymmetric synthesis. D/L-Leucinol is considered a valuable chemical in the fields of organic chemistry and drug development due to its unique stereochemistry and versatile reactivity.

Uses

Used in Pharmaceutical Industry:
D/L-Leucinol is used as a building block for the synthesis of pharmaceuticals and other organic compounds, taking advantage of its chiral nature and versatile reactivity.
Used in Chemical Industry:
D/L-Leucinol is used as a chiral reagent in asymmetric synthesis, contributing to the development of enantioselective reactions and the production of enantiomerically pure compounds.
Used in Organic Chemistry Research:
D/L-Leucinol is utilized in the study of stereochemistry and the development of novel synthetic methods, further expanding its applications in the field of organic chemistry.

Upstream product

• 23032-21-5 D-leucine methyl ester 
• 18869-43-7 DL-leucine methyl ester 
• 2899-43-6 DL-leucine ethyl ester 
• 615-82-7 DL-Leucyl-glycin 
• 328-39-2 LEUCINE 
• 4071-36-7 ethyl N-acetyl-leucinate 
• 37763-22-7 D-leucine ethyl ester 
• 328-38-1 (R)-leucine 
• 5845-53-4 (R)-leucine methyl ester hydrochloride 
• 73913-65-2 D-(-)-leucine ethyl ester hydrochloride 

Downstream Products

• 20826-31-7 (+/-)-2-(2,4-dinitro-anilino)-4-methyl-pentan-1-ol 
• 89218-13-3 2-[(E)-2-(Diphenyl-phosphinoyl)-vinylamino]-4-methyl-pentan-1-ol 
• 13892-89-2 (R)-2-amino-1-bromo-4-methylpentane hydrobromide 
• 137935-20-7 1-Benzyl-3-(1-hydroxymethyl-3-methyl-butyl)-thiourea 
• 86910-45-4 (R)-4-Methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-pentan-1-ol 
• 86941-40-4 (R)-2-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-4-methyl-pentan-1-ol 
• 87601-32-9 Toluene-4-sulfonic acid (R)-4-methyl-2-(toluene-4-sulfonylamino)-pentyl ester 
• 307532-07-6 (2R)-2-(dibenzylamino)-4-methylpentan-1-ol 
• 154-92-7 Nα-benzoyl-L-arginine 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 190275-62-8 N-(4-fluorophenylsulfonyl)-D-valyl-D-leucinol 
• 502545-85-9 N-(4-fluorophenylsulfonyl)-L-valyl-D-leucinol 

Relevant articles and documents

Enantio- and Diastereodivergent Sequential Catalysis Featuring Two Transition-Metal-Catalyzed Asymmetric Reactions

This study demonstrates the feasibility and inherent benefits of combining two distinct asymmetric transition-metal-catalyzed reactions in one pot. The reported transformation features a Pd-catalyzed asymmetric allylic alkylation and a Rh-catalyzed enantioselective 1,4-conjugate addition, effectively converting simple allyl enol carbonate precursors into enantioenriched cyclic ketones with two remote stereocenters. Despite the anticipated challenges associated with controlling stereoselectivity in such a complex system, the products are obtained in enantiomeric excesses ranging up to >99 % ee, exceeding those obtained from either of the individual asymmetric reactions. In addition, since the stereoselectivity of both steps is under catalyst control, this one-pot reaction is enantio- and diastereodivergent, enabling facile access to all stereoisomers from the same set of starting materials.

Design, Synthesis, Fungicidal Activity, and Unexpected Docking Model of the First Chiral Boscalid Analogues Containing Oxazolines

Chirality greatly influences the biological and pharmacological properties of a pesticide and will contribute to unnecessary environmental loading and undesired ecological impact. No structure and activity relationship (SAR) of enantiopure succinate dehydrogenase inhibitors (SDHIs) was documented during the structure optimization of boscalids. On the basis of commercial SDHIs, oxazoline natural products, and versatile oxazoline ligands in organic synthesis, the first effort was devoted to explore the chiral SDHIs and the preliminary mechanism thereof. Fine-tuning furnished chiral nicotinamides 4ag as a more promising fungicidal candidate against Rhizoctonia solani, Botrytis cinerea, and Sclerotinia sclerotiorum, with EC50 values of 0.58, 0.42, and 2.10 mg/L, respectively. In vivo bioassay and molecular docking were investigated to explore the potential in practical application and plausible novelty in action mechanism, respectively. The unexpected molecular docking model showed the different chiral effects on the binding site with the amino acid residues. This chiral nicotinamide also featured easy synthesis and cost-efficacy. It will provide a powerful complement to the commercial SDHI fungicides with the introduction of chirality.

The first synthesis of β-amino phosphonates using cyclic sulfamidates

Cyclic sulfamidates (prepared from α-amino acids and β-amino alcohols) have been used for the first time for the synthesis of novel β-amino phosphonates (chiral and achiral) by treatment with dialkyl phosphites using sodium hydride. 2-Substituted and 1,2-disubtituted β-amino phosphonates have efficiently been prepared following this method. The products are formed in high yield (79-84%) within 8-12 h.