(1S,2R)-(-)-cis-1-Amino-2-indanol

Base Information

• Chemical Name: (1S,2R)-(-)-cis-1-Amino-2-indanol
• CAS No.: 126456-43-7
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.192
• Hs Code.: 29052900
• UNII: LU3GK925A8
• DSSTox Substance ID: DTXSID10155191,DTXSID601335000
• Nikkaji Number: J655.021E
• Wikidata: Q27283183
• Mol file: 126456-43-7.mol

Synonyms:1H-Inden-2-ol,1-amino-2,3-dihydro-, (1S-cis)-;(-)-cis-1-Aminoindan-2-ol;(1S)-Amino-(2R)-indanol;(1S,2R)-(-)-1-Amino-2-indanol;(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol;(1S,2R)-1-Aminoindan-2-ol;(1S-cis)-1-Amino-2-indanol;(2R-cis)-1-Amino-2,3-dihydro-1H-inden-2-ol;2(R)-Hydroxy-1(S)-aminoindane;[(1S,2R)-2-Hydroxy-2,3-dihydro-1H-inden-1-yl]amine;(1S,2R)-(+)-cis-1-Aminoindan-2-ol;

Chemical Property of (1S,2R)-(-)-cis-1-Amino-2-indanol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 118-121 °C(lit.)
• Refractive Index: 1.5760 (estimate)
• Boiling Point: 290.031 °C at 760 mmHg
• PKA: 14.79±0.40(Predicted)
• Flash Point: 129.207 °C
• PSA: 46.25000
• Density: 1.212 g/cm³
• LogP: 1.30370
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• Solubility.: soluble in Methanol
• Water Solubility.: slightly soluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98% min ^*data from raw suppliers

[1S- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C2=CC=CC=C21)N)O
• Isomeric SMILES: C1[C@H]([C@H](C2=CC=CC=C21)N)O
• Uses: 1S,2R)-(-)-cis-1-Amino-2-indanol may be used to prepare:(-)-1,2,5,6-Tetrahydropyridine by reacting with methyl (E,E)-4-oxo-2-[(2,6,6-trimethylcyclohex-1-enyl)vinyl}but-2-enoate.Oxazaborolidine catalysts, which can catalyze the asymmetric reduction of aromatic ketones with high enantioselectivity.(RS,1S,2R)-(-)-2,4,6-Trimethylbenzenesulfinic acid 1-(2,4,6-trimethylbenzenesulfonylamino)indan-2-yl ester. (1S,2R)-(-)-cis-1-Amino-2-indanol is used as a reagent in the synthesis of heterocyclic compounds as integrase inhibiting antiviral agents. It is also a key intermediate of the HIV protease inhibitor, Indinavir (I525000).

Technology Process of (1S,2R)-(-)-cis-1-Amino-2-indanol

There total 105 articles about (1S,2R)-(-)-cis-1-Amino-2-indanol 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: 98.3%

(1S,2R)-1-azido-2,3-dihydro-1H-inden-2-ol (172881-85-5) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 750.06 Torr;

DOI:10.1055/s-1996-4328

Reference yield: 93.0%

(L)-phenylalanine <2(R)-hydroxy-1(S)-indanyl>amide (140468-56-0) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With sodium hydroxide; In ethanol; for 16h; Heating;

DOI:10.1021/jm00088a003

Reference yield: 92.0%

(3aS,8aR)-2-Phenyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazole (176587-85-2) → (1S,2R)-1-amino-2-indanol (7480-35-5,13286-59-4,74165-73-4,126456-43-7,136030-00-7,140632-19-5,140632-20-8)

Guidance literature:

With sulfuric acid; In dichloromethane; for 10h; Heating;

DOI:10.1021/jm9508696

upstream raw materials:

3,3α,8,8α-tetrahydro-2H-indeno[1,2-d]oxazol-2-one

2-phenyl-3a,8a-dihydro-8(H)-indeno<1,2-d>oxazole

2,3-dihydro-1H-indene 2,3-oxide

cis-indane-1,2-diol

Downstream raw materials:

(+)-trans-1-Amino-indan-2-ol

(-)-trans-1-Amino-indan-2-ol

(+/-)-trans-1-Benzylamino-indan-2-ol

(S)-2-(tert-butoxycarbonylamino)-N-((1S,2R)-2-hydroxy-1-indanyl)-3-phenylpropanamide

Refernces

• 1、 Ghosh, Arun K.,Kincaid, John F.,Haske, Michael G.. "A convenient enzymatic route to optically active 1-aminoindan-2-ol: Versatile ligands for HIV-1 protease inhibitors and asymmetric syntheses". . p. 541 - 544. Retrieved 1997.
• 2、 Pinxterhuis, Erik B.,Gualtierotti, Jean-Baptiste,Wezenberg, Sander J.,de Vries, Johannes G.,Feringa, Ben L.. "Highly Efficient and Robust Enantioselective Liquid–Liquid Extraction of 1,2-Amino Alcohols utilizing VAPOL- and VANOL-based Phosphoric Acid Hosts". . p. 178 - 184. Retrieved 2018.
• 3、 Sakurai, Rumiko,Sakai, Kenichi. "Resolution of racemic cis-1-amino-2-indanol by diastereomeric salt formation with (S)-2-phenylpropionic acid". . p. 411 - 413. Retrieved 2003.
• 4、 Zhou, Zijun,Tan, Yuqi,Shen, Xiang,Ivlev, Sergei,Meggers, Eric. "Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion". . p. 452 - 458. Retrieved 2020/12/31.
• 5、 Zhang, Jian-Dong,Chang, Ya-Wen,Dong, Rui,Yang, Xiao-Xiao,Gao, Li-Li,Li, Jing,Huang, Shuang-Ping,Guo, Xing-Mei,Zhang, Chao-Feng,Chang, Hong-Hong. "Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase". . p. 124 - 128. Retrieved 2020/09/21.