(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine

Base Information

• Chemical Name: (1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine
• CAS No.: 146504-07-6
• Molecular Formula: C11H22N2O2
• Molecular Weight: 214.308
• Hs Code.: 29242990
• European Community (EC) Number: 625-193-4,676-381-8
• DSSTox Substance ID: DTXSID00929883
• Nikkaji Number: J1.115.372K
• Wikidata: Q72449088
• Mol file: 146504-07-6.mol

Synonyms:137731-41-0;146504-07-6;N-Boc-trans-1,2-diaminocyclohexane;(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine;tert-Butyl ((1R,2R)-2-aminocyclohexyl)carbamate;tert-Butyl (trans-2-aminocyclohexyl)carbamate;tert-butyl N-[(1R,2R)-2-aminocyclohexyl]carbamate;tert-butyl (1R,2R)-2-aminocyclohexylcarbamate;(1R,2R)-N-Boc-1,2-cyclohexanediamine;trans-N-Boc-1,2-diaminocyclohexane;(1R,2R)-2-Amino-1-(Boc-amino)cyclohexane;trans-n-boc-1,2-cyclohexanediamine;Carbamic acid, (2-aminocyclohexyl)-, 1,1-dimethylethyl ester, trans-;1-n-boc-1,2-trans-cyclohexyldiamine;trans-N1-Boc-cyclohexane-1,2-diamine;n-boc-trans-1,2-cyclohexanediamine;MFCD08726023;MFCD06795909;SCHEMBL1045289;DTXSID00929883;CHEBI:192567;N-Boc-trans-1,2-damnocyclohexane;AMY24032;CS-D0336;s3896;AKOS015854135;trans,1n-boc-cyclohexane-1,2-diamine;1-n-boc-1(r),2(r)-cyclohexyldiamine;CCG-266681;DS-7843;carbamic acid, n-[(1r,2r)-2-aminocyclohexyl]-, 1,1-dimethylethyl ester, rel-;1-n-boc-1(r), 2(r)-cyclohexyldiamine;tert-Butyl trans-2-aminocyclohexylcarbamate;(1R,2R)-1-(Boc-amino)cyclohexan-2-amine;A2968;A3198;B5647;EN300-45538;EN300-258219;(1R,2R)-N-(tert-Butoxycarbonylamino]cyclohexane;N-Boc-trans-1,2-diaminocyclohexane, AldrichCPR;TRANS-1-AMINO-2-(BOC-AMINO)-CYCLOHEXANE;N-(t-butoxycarbonyl)-trans-1,2-diaminocyclohexane;J-007053;J-523520;tert-Butyl hydrogen (2-aminocyclohexyl)carbonimidate;(1R,2R)-1-AMINO-2-(BOC-AMINO)-CYCLOHEXANE;(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine, 97%;1,1-Dimethylethyl (trans-2-aminocyclohexyl)carbamate;(1R,2R)-N-tert.-Butoxycarbonylcyclohexane-1,2-diamine;F8887-8832;rac-tert-butyl N-[(1R,2R)-2-aminocyclohexyl]carbamate;trans-(2-aminocyclohexyl)-carbamic acid tert-butyl ester;trans-1-Amino-2-((tert-butoxycarbonyl)amino)cyclohexane;Z558512334;(+/-)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexane-diamine;(+/-)-trans-N-tert-butoxycarbonyl-1,2-cyclohexanediamine;(1R,2R)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine;trans-(2-amino-cyclohexyl)-carbamic acid tert-butyl ester;((1R,2R)-2-Amino-cyclohexyl)-carbamic acid tert-butyl ester;(1R)-N-(tert-Butoxycarbonyl)cyclohexane-1beta,2alpha-diamine;Carbamic acid, N-?[(1R,?2R)?-?2-?aminocyclohexyl]?-?, 1,?1-?dimethylethyl ester

Chemical Property of (1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine

Chemical Property:

• Melting Point: 114-115℃
• Boiling Point: 322.1 °C at 760 mmHg
• PKA: 12.26±0.40(Predicted)
• Flash Point: 148.6 °C
• PSA: 64.35000
• Density: 1.02 g/cm³
• LogP: 2.87220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 214.168127949
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

99.3% ^*data from raw suppliers

tert-Butyl((1R,2R)-2-Aminocyclohexyl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCCCC1N
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1N
• Uses: (1R,2R)-trans-N-Boc-1,2-cyclohexanediamine can be used as:An organocatalyst in the intramolecular desymmetrization of cyclohexanones to yield 2-azabicyclo[3.3.1]nonane.A starting material in the synthesis of a chiral nickel catalyst applicable for the Michael addition reaction of 1,3-dicarbonyl compounds to yield nitroalkenes.

Technology Process of (1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine

There total 12 articles about (1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine 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: 98.0%

C22H25N2O4C5H9O2 (315179-47-6) → tert-butyl ((1R,2R)-2-aminocyclohexyl)carbamate (146504-07-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 2h; under 760.051 Torr;

DOI:10.1021/jo000821m

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → tert-butyl ((1R,2R)-2-aminocyclohexyl)carbamate (146504-07-6)

Guidance literature:

In 1,4-dioxane; for 22h;

DOI:10.1039/b102180j

Reference yield: 53.6%

di-tert-butyl dicarbonate (24424-99-5) + (S,S)-1,2-diaminocyclohexane (21436-03-3) → tert-butyl ((1R,2R)-2-aminocyclohexyl)carbamate (146504-07-6)

Guidance literature:

In 1,4-dioxane; at 0 - 27 ℃; for 16h;

upstream raw materials:

di-tert-butyl dicarbonate

(1R,2R)-1,2-diaminocyclohexane

{[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile

C₂₂H₂₅N₂O₄C₅H₉O₂

Downstream raw materials:

(R,R)-N-propargyl-N’-tert-butoxycarbonyl-1,2-diaminocyclohexane

C₁₇H₂₅N₃O₂

N¹-monobenzyl,N²-Boc-(1R,2R)-diaminocyclohexane

(1R,2R)‐N-benzylcyclohexane‐1,2‐diamine

Refernces

• 1、 Sun, Yanyan,Liu, Fei,Gou, Shaohua,Cheng, Lin,Fang, Lei,Yin, Runting. "Synthesis and in vitro antiproliferative activity of platinum(II) complexes with N-monoalkyl 1R,2R-diaminocyclohexane as ligands". . p. 297 - 306. Retrieved 2012.
• 2、 Mohan Nalluri, Siva Krishna,Zhou, Jiawang,Cheng, Tao,Liu, Zhichang,Nguyen, Minh T.,Chen, Tianyang,Patel, Hasmukh A.,Krzyaniak, Matthew D.,Goddard, William A.,Wasielewski, Michael R.,Stoddart, J. Fraser. "Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based Rigid Isosceles Triangles in the Solid State". . p. 1290 - 1303. Retrieved 2019.
• 3、 Gilheany, Declan G.,Kavanagh, Saranna E.. "Harnessing the Power of the Asymmetric Grignard Synthesis of Tertiary Alcohols: Ligand Development and Improved Scope Exemplified by One-Step Gossonorol Synthesis". supporting information. p. 8198 - 8203. Retrieved 2020/11/18.