2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride

Base Information

• Chemical Name: 2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride
• CAS No.: 5588-52-3
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• DSSTox Substance ID: DTXSID40389083
• Mol file: 5588-52-3.mol

Synonyms:2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride;DTXSID40389083

Chemical Property of 2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride

Chemical Property:

• Vapor Pressure: 9.2E-09mmHg at 25°C
• Boiling Point: 463.3°Cat760mmHg
• Flash Point: 234°C
• PSA: 29.54000
• Density: 1.5g/cm³
• LogP: 1.34290
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 312.0625326
• Heavy Atom Count: 21
• Complexity: 420

Purity/Quality:

99% ^*data from raw suppliers

rac-(1S,2R,8S)-14-Oxa-7-azatetracyclo[6.6.1.0~1,11~.0~2,7~]pentadeca-9,11-dien-13-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C(=O)C(=NNC2=CC=CC=C2[N+](=O)[O-])Cl

Technology Process of 2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride

There total 16 articles about 2-morpholin-4-yl-N-(2-nitrophenyl)-2-oxoethanehydrazonoyl chloride 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: 87.0%

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene (651738-07-7) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene; With trifluoroacetic acid; at 20 ℃; for 0.25h;

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ol0361251

Reference yield: 82.0%

(1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one (1126784-60-8) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate; In N,N-dimethyl acetamide; at 100 ℃; for 12h;

DOI:10.1039/b816576a

Reference yield:

tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate (708260-76-8) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 78 percent / PdCl₂(PPh₃)2; tetrabutylammonium bromide; PPh₃ / Na₂CO₃ / dimethylformamide / 90 °C

2.1: 64 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 0.75 h / Heating

3.1: trifluoroacetic acid / CHCl₃ / 20 °C

3.2: 53 percent / K₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / sonication

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; tetrabutylammomium bromide; triphenylphosphine; trifluoroacetic acid; dibenzoyl peroxide; sodium carbonate; In tetrachloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Heck reaction;

DOI:10.1021/ol049455+

upstream raw materials:

(RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene

tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate

tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate

Downstream raw materials:

1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate

Tetrahydrosecurinin

Tetrahydrosecurinin

(2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one