180683-64-1

Basic information

• Product Name: (1S,2S)-Boc-1,2-diaminocyclohexane
• Synonyms: 1-N-BOC-1(S), 2(S)-CYCLOHEXYLDIAMINE;(1S,2S)-Boc-1,2-diaminocyclohexane;(1S,2S)-trans-N-Boc-1,2-Cyclohexanediamine;1-N-Boc-(1S,2S)-(+)-1,2-Diaminocyclohexane;N-tert-Butoxycarbonyl-S,S-1,2-diaminocyclohexane;Carbamic acid, [(1S,2S)-2-aminocyclohexyl]-, 1,1-dimethylethyl ester (9CI);(1S)-trans-N-Boc-1,2-diaminocyclohexane;Trans (1S,2S)-1N-Boc-cyclohexane-1,2-diamine
• CAS NO: 180683-64-1
• Molecular Formula: C₁₁H₂₂N₂O₂
• Molecular Weight: 214.30458
• Product Categories: API intermediates
• Mol File: 180683-64-1.mol

Chemical Properties

• Melting Point: 118-119 °C
• Boiling Point: 322.1 °C at 760 mmHg
• Flash Point: 148.6 °C
• Appearance: /
• Density: 1.02 g/cm³
• Vapor Pressure: 0.000286mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.26±0.40(Predicted)
• BRN: 7745537
• CAS DataBase Reference: (1S,2S)-Boc-1,2-diaminocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-Boc-1,2-diaminocyclohexane(180683-64-1)
• EPA Substance Registry System: (1S,2S)-Boc-1,2-diaminocyclohexane(180683-64-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 180683-64-1(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C11H22N2O2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8(9)12/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 21436-03-3 (S,S)-1,2-diaminocyclohexane 
• 880644-81-5 C₂₇H₃₄N₂O₆ 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1190086-92-0 (1S,2S)-tert-butyl-N-[2-(diallylamino)cyclohexyl]carbamate 
• 34619-03-9 tert-butyldicarbonate 
• 870-46-2 t-butoxycarbonylhydrazine 

Downstream Products

• 199336-09-9 {(1S,2S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid tert-butyl ester 
• 366496-56-2 4,4'-bis(1-carbonyl-2-tert-butoxycarbonyl-S,S-1,2-diaminocyclohexyl)-2,2'-bipyridine 
• 910117-05-4 N-(2-tert-butoxycarbonylamino-cyclohexyl)-oxalamic acid ethyl ester 
• 193621-93-1 [[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 193621-92-0 [[2-(6-Benzyloxycarbonylamino-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 193621-94-2 [[2-(2-Benzyloxycarbonylamino-6-oxo-1,6-dihydro-purin-9-yl)-acetyl]-((1S,2S)-2-tert-butoxycarbonylamino-cyclohexyl)-amino]-acetic acid ethyl ester 
• 180509-99-3 {((1S,2S)-2-tert-Butoxycarbonylamino-cyclohexyl)-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid methyl ester 
• 445478-72-8 [(1S,2S)-2-{[([3-(trifluoromethyl)benzoyl]amino)acetyl]amino}cyclohexyl]carbamic acid 1,1-dimethylethyl ester 
• 1142953-14-7 1,3-bis-((1S,2S)-2-tert-butoxycarbonylaminocyclohexylsulfamoyl)-benzene 

Relevant articles and documents

Preparation method of N-Boc-trans-cyclohexanediamine

The invention discloses a preparation method of N-Boc-trans-cyclohexanediamine, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: dissolving trans-1, 4-cyclohexanediamine or (1S, 2S)-1, 2-cyclohexanediamine, tert-butyloxycarborylhydrazine and a copper catalyst in an organic solvent, and adding hydrogen peroxide to obtain the N-Boc-trans-cyclohexanediamine by a one-pot method. The method disclosed by the invention is simple to operate, and by controlling the equivalent weight of hydrogen peroxide, the temperature and the solvent concentration, the generation of a bis-t-butyloxycarboryl protecting group is effectively reduced, and the sufficient reaction of the raw material cyclohexanediamine is realized.

Directing the Solid-State Organization of Racemates via Structural Mutation and Solution-State Assembly Processes

Chirality plays a central role in biomolecular recognition and pharmacological activity of drugs and can even lead to new functions such as spin filters. Although there have been significant advances in understanding and controlling the helical organizati

Design, synthesis, and biological evaluation of radioiodinated benzo[d]imidazole-quinoline derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging

Several malignant tumors and fibrotic diseases are associated with PDGFRβ overexpression and excessive signaling, making this receptor attractive for molecular targeting and imaging approaches. A series of benzo[d]imidazole-quinoline derivatives were designed and synthesized to develop radioiodinated compounds as PDGFRβ-specific imaging probes. The structure activity relationship (SAR) evaluation of the designed compounds was performed. Among them, 2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (5a) and 4-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (5d) exhibited a relatively high PDGFRβ-TK inhibitory potency, whereas iodinated 5a derivative 5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (8) exhibited a superior inhibitory potency as PDGFRβ inhibitor than iodinated 5d derivative 4-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (11). Furthermore, [125I]8 and [125I]11 were synthesized and evaluated for PDGFRβ radioligand ability, both in vitro and in vivo. Cellular uptake experiments showed that [125I]8 had a higher uptake in BxPC3-luc cells as PDGFRβ-positive cells than [125I]11. Incubation of [125I]8 after pretreatment of PDGFRβ ligands significantly reduced the uptake of [125I]8. In biodistribution experiments using tumor-bearing mice, [125I]8 accumulation in the tumor 1 h postinjection was higher than that of the benzo[d]imidazol-quinoline derivative [125I]IIQP, used in our previous research. These results indicate that [125I]8 could be a promising PDGFRβ imaging agent. Although its clinical application requires further structural modifications, the results obtained in this research may be useful for the development of PDGFRβ-specific radioligands.

“Backdoor Induction” of Chirality: Trans-1,2-cyclohexanediamine as Key Building Block for Asymmetric Hydrogenation Catalysts

This paper describes the synthesis and characterization of 21 chiral monodentate ligands L, assembled of three building blocks utilizing amide bonds: a metal binding triphenylphosphine, a chiral cyclic diamine and an additional substituent for fine-tuning the steric and/or electronic properties. Cis square-planar metal complexes of RhI and PtII with ML2 stoichiometry have been prepared and characterized by spectroscopic methods (NMR, IR, UV-Vis, CD) and DFT calculations. A key feature of the metal complexes is a prochiral metal coordination sphere and “backdoor induction” of chirality from a distant chiral source via an outer-coordination sphere, well-defined by aromatic stacking and hydrogen-bonding. The rhodium complexes were used as catalysts in asymmetric hydrogenation of α,β-dehydroamino acids with excellent yield and selectivity (up to 97 % ee), strongly supporting the “backdoor induction” hypothesis.

Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins

An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).

Solvent-induced reversal of enantioselectivity in the synthesis of succinimides by the addition of aldehydes to maleimides catalysed by carbamate-monoprotected 1,2-diamines

A simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly disubstituted, to maleimides catalysed by chiral carbamate-monoprote

Synthesis of novel macrocyclic tetraamides

A simple and facile route has been described for the synthesis of macrocyclic tetraamides. This method is applicable for the preparation of a variety of macrocyclic tetraamides of various heteroatom substitutions.

Solvent-dependent enantioswitching in the Michael addition of α,α-disubstituted aldehydes to maleimides organocatalyzed by mono-N-Boc-protected cyclohexa-1,2-diamines

Enantiomerically pure mono-N-Boc-protected trans-cyclohexa-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides. Using a single enantiomer of the organocatalyst, both enantiomeri

Multivalent, high-relaxivity MRI contrast agents using rigid cysteine-reactive gadolinium complexes

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Direct asymmetric aldol reaction catalyzed by C2-Symmetrical chiral primary amine organocatalysts

Three novel C2-symmetrical chiral primary amines were synthesized from chiral BINOL and diamines. Then their catalytic activities in the asymmetric aldol reactions were evaluated, and the result indicated that 1c was the optimal organocatalyst.