Phaseolin; Phaseolin (phytoalexin)

Base Information

• Chemical Name: Phaseolin; Phaseolin (phytoalexin)
• CAS No.: 13401-40-6
• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.361
• DSSTox Substance ID: DTXSID20871956
• Wikidata: Q105158582
• Mol file: 13401-40-6.mol

Synonyms:17,17-Dimethyl-4,12,18-trioxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol;Phaseolin;Phaseolin (phytoalexin);SCHEMBL33735;DTXSID20871956;6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f]bis[1]benzopyran-10-ol, 9CI;(2R,11R)-17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0^{2,11.0^{5,10.0^{14,19]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol;3,3-Dimethyl-6b,12b-dihydro-3H,7H-pyrano[2',3':6,7][1]benzofuro[3,2-c][1]benzopyran-10-ol

Chemical Property of Phaseolin; Phaseolin (phytoalexin)

Chemical Property:

• Vapor Pressure: 2.32E-09mmHg at 25°C
• Melting Point: 177-178°
• Refractive Index: 1.628
• Boiling Point: 467.473 °C at 760 mmHg
• PKA: 9.13(at 25℃)
• Flash Point: 236.519 °C
• PSA: 47.92000
• Density: 1.287 g/cm³
• LogP: 4.18610
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 322.12050905
• Heavy Atom Count: 24
• Complexity: 530

Purity/Quality:

99% ^*data from raw suppliers

Phaseollin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=CC3=C2OC4C3COC5=C4C=CC(=C5)O)C

Technology Process of Phaseolin; Phaseolin (phytoalexin)

There total 6 articles about Phaseolin; Phaseolin (phytoalexin) 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:

3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one (91078-13-6) → (+/-)-phaseollin (13401-40-6,91110-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 37 percent / MCPBA / CH₂Cl₂ / 25 h / Ambient temperature

2: 82 percent / toluene / 0.5 h / Heating

3: 1.) 3 M HCl; 2.) 2 M NaOH, NaBH₄ / 1.) methanol, reflux, 25 min.; 2.) methanol, 48 h.

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene;

Reference yield:

3-(5-methoxymethoxy-2,2-dimethyl-3-phenylsulphinylchroman-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one (111492-47-8) → (+/-)-phaseollin (13401-40-6,91110-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / toluene / 0.5 h / Heating

2: 1.) 3 M HCl; 2.) 2 M NaOH, NaBH₄ / 1.) methanol, reflux, 25 min.; 2.) methanol, 48 h.

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; In toluene;

Reference yield:

3-(2-hydroxy-4-methoxymethoxyphenyl)-1,1-dimethoxy-2-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl)-propan-3-one (111492-46-7) → (+/-)-phaseollin (13401-40-6,91110-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / sodium methoxyde / methanol / 0.5 h / Heating

2: 37 percent / MCPBA / CH₂Cl₂ / 25 h / Ambient temperature

3: 82 percent / toluene / 0.5 h / Heating

4: 1.) 3 M HCl; 2.) 2 M NaOH, NaBH₄ / 1.) methanol, reflux, 25 min.; 2.) methanol, 48 h.

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sodium methylate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; toluene;

upstream raw materials:

glabrone

3-(5-methoxymethoxy-2,2-dimethyl-2H-benzo-pyran-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one

1,1-dimethoxy-2-(5-methoxymethoxy-2,2-dimethyl-2H-benzopyran-6-yl)-3-(2-hydroxy-4-methoxymethoxyphenyl)propane-3-one

3-(5-methoxymethoxy-2,2-dimethyl-3-phenylthiochroman-6-yl)-7-methoxymethoxy-4H-benzopyran-4-one

Refernces

• 1、 Thomas, Phillip,Whiting, Donald A.. "SYNTHESIS OF (+/-)-PHASEOLLIN; A PROTECTIVE SEQUENCE FOR CHROMEN DOUBLE BONDS". . p. 1099 - 1102. Retrieved 2007/10/02.