(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Base Information

• Chemical Name: (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
• CAS No.: 175166-49-1
• Molecular Formula: C21H18 N2 O2
• Molecular Weight: 330.386
• Hs Code.: 29349990
• European Community (EC) Number: 634-008-6
• DSSTox Substance ID: DTXSID10452334
• Nikkaji Number: J734.800B
• Wikidata: Q72490394
• Mol file: 175166-49-1.mol

Synonyms:175166-49-1;(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole];Bis((3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)methane;(3aR,8bS)-2-[[(3aR,8bS)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]methyl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole;(-)-2,2/'-METHYLENEBIS[(3AS,8AR)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE];SCHEMBL15248779;DTXSID10452334;BDHSVQLSNIGJNC-JYWFKMLOSA-N;(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8Hindeno[;MFCD00799561;AKOS015838880;AKOS015904445;CS-W009418;SC11791;8H-Indeno[1,2-d]oxazole, 2,2'-methylenebis[3a,8a-dihydro-, (3aS,3'aS,8aR,8'aR)-;AS-73642;BP-12947;T71934;A881622;J-011072;bis((3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)methane;Bis(3aalpha,8aalpha-dihydro-8H-indeno[1,2-d]oxazole-2-yl)methane;(3aS,3'aS,8aR,8'aR)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole], 98%;(3aS,8aR,3a'S,8a'R)-2,2'-Methylenebis(8,8a-dihydro-3aH-indeno[1,2-d][1,3]oxazole);(3aS,8aR)-2-{[(3aS,8aR)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-yl]methyl}-3aH,8H,8aH-indeno[1,2-d][1,3]oxazole;[3aR-[2(3'aR,8'aS),3'a beta ,8'a beta ]]-(+)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-]oxazole];[3aS-[2(3'aR*,8'aS*),3'a alpha ,8'a alpha ]]-(-)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole];[3AS-[2(3'AR*,8'AS*),3'AALPHA,8'AALPHA]]-(-)-2,2'-METHYLENEBIS[3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]

Chemical Property of (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Chemical Property:

• Melting Point: 224 °C
• Refractive Index: -360 ° (C=1, CH2Cl2)
• Boiling Point: 493.2°Cat760mmHg
• PKA: 5.47±0.20(Predicted)
• Flash Point: 201.9°C
• PSA: 43.18000
• Density: 1.48g/cm³
• LogP: 2.43710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: almost transparency in Dichloromethane
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 330.136827821
• Heavy Atom Count: 25
• Complexity: 563

Purity/Quality:

98%，99%ee ^*data from raw suppliers

(-)-2,2''-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8Hindeno[1,2-d]oxazole] ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C(C3=CC=CC=C31)N=C(O2)CC4=NC5C(O4)CC6=CC=CC=C56
• Isomeric SMILES: C1[C@@H]2[C@H](C3=CC=CC=C31)N=C(O2)CC4=N[C@@H]5[C@H](O4)CC6=CC=CC=C56
• Uses: (3aS,3′aS,8aR,8′aR)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] can be used as a chiral ligand:In the preparation of oxazole α-hydroxy esters through intermolecular Alder-Ene reaction.In the atom transfer radical polymerization reactions of methyl methacrylate.In the copper-catalyzed synthesis of isoxazolidine derivatives by reacting nitrone with α,β-unsaturated acyl?phosphonate.

Technology Process of (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

There total 4 articles about (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] 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: 89.0%

diethyl malonoimidate dihydrochloride (10344-69-1) + (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) → [3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (175166-49-1)

Guidance literature:

In dichloromethane; Inert atmosphere; Reflux;

DOI:10.1016/j.catcom.2009.10.029

Reference yield: 80.0%

cis-1,2-indandiol (4370-02-9,4647-42-1,4647-43-2,67528-23-8,71214-80-7,71214-82-9,78737-68-5,67528-22-7) + malononitrile (109-77-3) → 2-indanone (615-13-4) + (3aS,8aR)-(8,8a-Dihydro-3aH-indeno[1,2-d]oxazol-2-yl)-acetonitrile (175166-50-4) + [3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (175166-49-1)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; Yields of byproduct given; -40 deg C to room t.;

DOI:10.1016/0040-4039(95)02328-3

Reference yield:

ethyl 3-amino-3-ethoxyprop-2-enimidate + (1R,2S)-amino indanol (142678-92-0) → [3aS-[2(3'aR*,8'aS*),3a,8a]]methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] (175166-49-1)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 72h;

DOI:10.1021/ol006500e

upstream raw materials:

cis-1,2-indandiol

malononitrile

(1S,2R)-1-amino-2-indanol

diethyl malonoimidate dihydrochloride

Downstream raw materials:

{3aS-[2(3'aR*,8'aS*),3aα,8aα]}-2,2'-(cyclopropylidene)-bis{3a,8a-dihydro-8H-indeno[1,2-d]-oxazole}

(3aS,3a'S,8aR,8a'R)-2,2'-(propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)

(3aS,3a'S,8aR,8a'R)-2,2'-(1,3-bis(4-(tert-butyl)phenyl)propane-2,2-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)

C₅₁H₆₂N₂O₂

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