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
• Article Data: 21

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

Downstream Products

• 180509-98-2 ((1S,2S)-2-tert-Butoxycarbonylamino-cyclohexylamino)-acetic acid methyl ester 
• 193621-90-8 ((1S,2S)-2-tert-Butoxycarbonylamino-cyclohexylamino)-acetic acid ethyl ester 
• 445478-72-8 [(1S,2S)-2-{[([3-(trifluoromethyl)benzoyl]amino)acetyl]amino}cyclohexyl]carbamic acid 1,1-dimethylethyl ester 
• 1630015-80-3 C₃₀H₄₆N₄O₆ 
• 199336-05-5 benzyl N-[(1S,2S)-2-aminocyclohexyl]carbamate 
• 1190087-04-7 (1S,2S)-tert-butyl-N-{2-[(methyl)(1-naphthylmethyl)amino]cyclohexyl}carbamate 
• 1353944-65-6 tert-butyl ((1S,2S)-2-(methylamino)cyclohexyl)carbamate 
• 1234860-01-5 (1S,2S)-N₁,N₁-dimethylcyclohexane-1,2-diamine hydrochloride 

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.

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.

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).