(1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine

Base Information

• Chemical Name: (1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine
• CAS No.: 75599-23-4
• Molecular Formula: C8H18N2
• Molecular Weight: 142.244
• European Community (EC) Number: 859-893-8
• Nikkaji Number: J817.569A
• Mol file: 75599-23-4.mol

Synonyms:75599-23-4;(1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine;cis-N1,N2-Dimethylcyclohexane-1,2-diamine;cis-N,N'-Dimethyl-1,2-cyclohexanediamine;(1R,2S)-N1,N2-dimethylcyclohexane-1,2-diamine;rel-(1R,2S)-N1,N2-Dimethylcyclohexane-1,2-diamine;SCHEMBL120496;(1R,2S)-1-N,2-N-dimethylcyclohexane-1,2-diamine;JRHPOFJADXHYBR-OCAPTIKFSA-N;AKOS006238849;CS-0058202;N,N'-Dimethyl-1alpha,2alpha-cyclohexanediamine;EN300-7141848

Chemical Property of (1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine

Chemical Property:

• Boiling Point: 186.8±8.0 °C(Predicted)
• PKA: 11.04±0.40(Predicted)
• PSA: 24.06000
• Density: 0.89±0.1 g/cm3(Predicted)
• LogP: 1.51820
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.146998583
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

cis-N,?N''-?Dimethyl-?1,?2-?cyclohexanediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1CCCCC1NC
• Isomeric SMILES: CN[C@@H]1CCCC[C@@H]1NC
• Uses: cis-N,?N''-?Dimethyl-?1,?2-?cyclohexanediamine is a reactant used in fluorinated 4-aminopyridine derivatives as well as a catalyst in the synthesis of blebbiastatin, a chemical tool.

Technology Process of (1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine

There total 19 articles about (1S,2R)-1-N,2-N-dimethylcyclohexane-1,2-diamine 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: 96.0%

N,N’-[(±)-trans-cyclohexane-1,2-diyl]diformamide → trans-N,N'-dimethylcyclohexane-1,2-diamine (61798-24-1,67579-81-1,68737-65-5,75599-23-4,87583-89-9,99295-66-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 16h;

DOI:10.1021/ja027433h

Reference yield: 89.0%

cis-cyclohexane-1,2-diamine (1436-59-5) + formic acid ethyl ester (109-94-4) → (1R,2S)-N1,N2- dimethylcyclohexane-1,2-diamine (75599-23-4)

Guidance literature:

cis-cyclohexane-1,2-diamine; formic acid ethyl ester; Reflux;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; Reflux;

With water; sodium hydroxide; In tetrahydrofuran;

Reference yield: 42.0%

trans-N,N'-dimethylcyclohexane-1,2-diamine (61798-24-1,67579-81-1,68737-65-5,75599-23-4,87583-89-9,99295-66-6) → (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane (61798-24-1,67579-81-1,68737-65-5,75599-23-4,99295-66-6,87583-89-9)

Guidance literature:

trans-N,N'-dimethylcyclohexane-1,2-diamine; With L-Tartaric acid; In ethanol; at 20 ℃; for 1h; Reflux; Resolution of racemate;

With potassium hydroxide; In dichloromethane; at 20 ℃; pH=9-10; Reflux; Resolution of racemate;

DOI:10.3184/174751913X13626731204890

upstream raw materials:

(S,S)-1,2-diaminocyclohexane-N,N'-diethyl carbamate

N-((1S,2S)-2-Formylamino-cyclohexyl)-formamide

(S,S)-1,2-diaminocyclohexane

7-methyl-7-azabicyclo[4.1.0]heptane

Downstream raw materials:

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

(1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane

Refernces

• 1、 Shen, Yan-Hong,Ye, Qing,Hou, Shao-Gang,Wang, Qun. "An efficient synthesis of enantiomerically pure trans-N1,N 2-dimethylcyclohexane-1,2-diamine". . p. 191 - 192. Retrieved 2013/07/27.
• 2、 Bilke, Julia L.,O'Brien, Peter. "On the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine: Probing the effect of the stoichiometric ligand". . p. 6452 - 6454. Retrieved 2008/12/21.