6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate

Base Information

• Chemical Name: 6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate
• CAS No.: 124753-65-7
• Molecular Formula: C₁₅H₁₇NO₄
• Molecular Weight: 275.304
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30924922
• Wikidata: Q82899145
• Mol file: 124753-65-7.mol

Synonyms:DTXSID30924922;6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate

Chemical Property of 6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 118-124oC
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 488.7°Cat760mmHg
• Flash Point: 249.4°C
• PSA: 75.63000
• Density: g/cm³
• LogP: 2.72310
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 274.10793299
• Heavy Atom Count: 20
• Complexity: 369

Purity/Quality:

≥ 99% (HPLC) ^*data from raw suppliers

cis-6-(Benzyloxycarbonylamino)-3-cyclohexene-1-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC(C1C(=O)[O-])NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1C=CC[C@@H]([C@@H]1C(=O)[O-])NC(=O)OCC2=CC=CC=C2

Technology Process of 6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate

There total 6 articles about 6-{[(Benzyloxy)(hydroxy)methylidene]amino}cyclohex-3-ene-1-carboxylate 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:

(1R,6S)-6-Benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid methyl ester (91259-90-4,91280-45-4,124753-67-9) → (1R,6S)-6-Benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (102508-02-1,124753-65-7,129313-92-4)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1021/ja00103a061

Reference yield:

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate (93603-11-3) → (1R,6S)-6-Benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (102508-02-1,124753-65-7,129313-92-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / acetone / 0 °C

2: NaN₃ / acetone

3: benzene / Heating

4: p-TsOH / benzene / Heating

5: aq. NaOH / methanol

With sodium hydroxide; sodium azide; toluene-4-sulfonic acid; triethylamine; In methanol; acetone; benzene;

DOI:10.1021/ja00103a061

Reference yield:

(1S,6R)-6-Isocyanato-cyclohex-3-enecarboxylic acid methyl ester → (1R,6S)-6-Benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (102508-02-1,124753-65-7,129313-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / benzene / Heating

2: aq. NaOH / methanol

With sodium hydroxide; toluene-4-sulfonic acid; In methanol; benzene;

DOI:10.1021/ja00103a061

upstream raw materials:

(1R,6S)-6-Benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid methyl ester

1-methyl hydrogen 1,2-cis-1,2-cyclohex-4-ene dicarboxylate

(cis)-6-aminocyclohex-3-ene-1-carboxylic acid

benzyl chloroformate

Downstream raw materials:

((1S,6R)-6-Hydroxymethyl-cyclohex-3-enyl)-carbamic acid benzyl ester

((1S,2R,5S)-7-Oxo-6-oxa-bicyclo[3.2.1]oct-2-yl)-carbamic acid benzyl ester