Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-

Base Information

• Chemical Name: Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-
• CAS No.: 58917-91-2
• Molecular Formula: C₂₀H₁₄O₃
• Molecular Weight: 302.329
• UNII: 8942B964DU,3AP071IXF4
• DSSTox Substance ID: DTXSID901031974,DTXSID701136015
• Nikkaji Number: J239.108B
• Wikidata: Q27256976
• Mol file: 58917-91-2.mol

Synonyms:63323-29-5;(+)-syn-BPDE;(+)-Benzo(a)pyrene-7,8-diol-9,10-epoxide, syn;BRN 4356684;UNII-3AP071IXF4;3AP071IXF4;Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-;(+)-BP-7-alpha,8-beta-diol-9-alpha,10-alpha-epoxide 1;(+)cis-7-alpha,8-beta-Dihydroxy-9-alpha,10-alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene;Benzo(a)pyrene, 7,8,9,10-tetrahydro-7-alpha,8-beta-dihydroxy-9-alpha,10-alpha-epoxy-, (+)-Z-;Benzo(a)pyrene, 7-alpha,8-beta-dihydroxy-9-alpha,10-alpha-epoxy-7,8,9,10-tetrahydro-, (+)-cis-;syn-(+-)-trans-7,8,9,10-Tetrahydrobenzo(a)pyrene-7,8-diol-9,10-epoxide;58917-91-2;8942B964DU;BENZO(10,11)CHRYSENO(3,4-B)OXIRENE-7,8-DIOL, 7,8,8A,9A-TETRAHYDRO-, (7S-(7.ALPHA.,8.BETA.,8A.BETA.,9A.BETA.))-;Benzo[10,11]chryseno[3,4-b]oxirene-7,8-diol, 7,8,8a,9a-tetrahydro-, [7S-(7.alpha.,8.beta.,8a.beta.,9a.beta.)]-;SYN-BPDE, (+)-;Benzo(10,11)chryseno(3,4-b)oxirene-7,8-diol, 7,8,8a,9a-tetrahydro-, (+-)-;SYN-BPDE, (+/-)-;DTXSID701136015;DTXSID901031974;Benzo(a)pyrene, 7,8,9,10-tetrahydro-7-beta,8-alpha-dihydroxy-9-beta,10-beta-epoxy-, (+-)-(Z)-;BENZO(A)PYRENEDIOLEPOXIDE, SYN-;LS-39979;LS-40072;Q27256976;syn-(+)-benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide;BENZO(A)PYRENE-7,8-DIHYDRODIOL 9,10-EPOXIDE, SYN-(+/-)-;SYN-BENZO(A)PYRENE-7,8-DIOL-9,10-EPOXIDE, (+)-TRANS-;SYN-BENZO(A)PYRENE-7,8-DIOL-9,10-EPOXIDE, (+/-)-TRANS-;(7S,8R,9S,10R)-(+)-SYN-BENZO(A)PYRENE-7,8-DIOL 9,10-EPOXIDE;(7S,8R,8aS,9aR)-7,8,8a,9a-Tetrahydrobenzo[10,11]chryseno[3,4-b]oxirene-7,8-diol;(7s,8r,9s,10r)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene;(7.ALPHA.,8.BETA.,9.ALPHA.,10.ALPHA.)-BENZO(A)PYRENE-7,8-DIHYDRODIOL-9,10-EPOXIDE;BENZO(10,11)CHRYSENO(3,4-B)OXIRENE-7,8-DIOL, 7,8,8A,9A-TETRAHYDRO-, (7.ALPHA.,8.BETA.,8A.BETA.,9A.BETA.)-(+/-)-;BENZO(10,11)CHRYSENO(3,4-B)OXIRENE-7,8-DIOL, 7,8,8A,9A-TETRAHYDRO-, (7R,8S,8AR,9AS)-REL-;BENZO(10,11)CHRYSENO(3,4-B)OXIRENE-7,8-DIOL, 7,8,8A,9A-TETRAHYDRO-, (7S,8R,8AS,9AR)-

Chemical Property of Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-

Chemical Property:

• Vapor Pressure: 5.73E-15mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 594.2°C at 760 mmHg
• PKA: 13.50±0.40(Predicted)
• Flash Point: 313.2°C
• PSA: 52.99000
• Density: 1.569g/cm³
• LogP: 3.43180
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 302.094294304
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

99% ^*data from raw suppliers

(7R,?8S,?8aR,?9aS)?-7,?8,?8a,?9a-?Tetrahydrobenzo[10,?11]?chryseno[3,?4-?b]?oxirene-?7,?8-?diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C6C(O6)C(C5O)O)C=C2
• Isomeric SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4[C@@H]6[C@@H](O6)[C@@H]([C@H]5O)O)C=C2
• Uses: (7R,8S,8aR,9aS)-7,8,8a,9a-Tetrahydrobenzo[10,11]chryseno[3,4-b]oxirene-7,8-diol is an intermediate in the synthesis of environmental pollutant and carcinogen in humans and rodents, used in the metabolic studies.

Technology Process of Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)-

There total 27 articles about Benzo(a)pyrene-7,8-dihydrodiol 9,10-epoxide, syn-(+)- 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:

C21H13ClO4 → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Yield given;

DOI:10.1021/ja00147a031

Reference yield:

1-bromopyrene (1714-29-0) → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) B(OMe)3, 3.) H₂O₂, 4.) t-BuNH₂, 5.) Et₃N

2: n-BuLi / tetrahydrofuran / 5 h / -78 - 20 °C

3: H₂ / PtO₂ / tetrahydrofuran / 4 h / 735.5 Torr / Ambient temperature

4: 1.) BF₃*OEt₂, NaI / 1.) CH₃CN, from 0 deg C to RT, 2 h, 2.) CH₂Cl₂, reflux, 3 h

5: BCl₃ / CH₂Cl₂ / 0.5 h / -20 °C

6: 4 M aq.NaOH / tetrahydrofuran / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; Trimethyl borate; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; boron trichloride; tert-butylamine; triethylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00147a031

Reference yield:

Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester (172533-57-2) → (+/-)-r-7,t-8-Dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (63323-30-8,55097-80-8,58917-67-2,58917-91-2,60268-85-1,60268-86-2,63323-29-5,63323-31-9,63357-09-5,64397-28-0,64912-49-8,64912-50-1,82111-22-6,111137-80-5,91327-01-4)

Guidance literature:

Multi-step reaction with 5 steps

1: n-BuLi / tetrahydrofuran / 5 h / -78 - 20 °C

2: H₂ / PtO₂ / tetrahydrofuran / 4 h / 735.5 Torr / Ambient temperature

3: 1.) BF₃*OEt₂, NaI / 1.) CH₃CN, from 0 deg C to RT, 2 h, 2.) CH₂Cl₂, reflux, 3 h

4: BCl₃ / CH₂Cl₂ / 0.5 h / -20 °C

5: 4 M aq.NaOH / tetrahydrofuran / 2 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; boron trichloride; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00147a031

upstream raw materials:

(-)-trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene

1-bromopyrene

Toluene-4-sulfonic acid 2-bromo-pyren-1-yl ester

(((2-bromo-1,3-phenylene)bis(oxy))bis(methylene))dibenzene

Downstream raw materials:

7,8,9,10-tetrahydroxytetrahydrobenzopyrene

(+/-)-7β,8α,9α,10α-tetrahydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene

7,8,9,10-tetrahydroxytetrahydrobenzo[a]pyrene

1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-((7R,8S,9R)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-benzo[def]chrysen-10-ylamino)-1H-pyrimidin-2-one

Refernces

• 1、 Koreeda, Masato,Gopalaswamy, Ramesh. "Regio- and stereocontrolled synthesis of the bay-region anti-diol epoxide metabolites of the potent carcinogens benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene". . p. 10595 - 10596. Retrieved 2007/10/02.
• 2、 Yagi,Thakker,Hernandez,Koreeda,Jerina. "Synthesis and reactions of the highly mutagenic 7,8 diol 9,10 epoxides of the carcinogen benzo[a]pyrene". . p. 1604 - 1611. Retrieved 2007/10/11.