1,4-Dihydro-1,4-methano-5,8-naphthalenediol

Base Information

• Chemical Name: 1,4-Dihydro-1,4-methano-5,8-naphthalenediol
• CAS No.: 3090-47-9
• Molecular Formula: C11H10 O2
• Molecular Weight: 174.199
• Hs Code.: 2907299090
• DSSTox Substance ID: DTXSID30883949
• Nikkaji Number: J421.657A
• Mol file: 3090-47-9.mol

Synonyms:1,4-Dihydro-1,4-methano-5,8-naphthalenediol;3090-47-9;1,4-dihydro-1,4-methanonaphthalene-5,8-diol;1,4-Methanonaphthalene-5,8-diol, 1,4-dihydro-;SCHEMBL2705391;DTXSID30883949;5,8-dihydroxy-1,4-dihydro-1,4-methanonaphthalene;5,8-Endomethylene-5,8-dihydro-1,4-naphthohydroquinone

Chemical Property of 1,4-Dihydro-1,4-methano-5,8-naphthalenediol

Chemical Property:

• Vapor Pressure: 0.101mmHg at 25°C
• Melting Point: 143-144 °C
• Boiling Point: 215.4°C at 760 mmHg
• PKA: 10.53±0.20(Predicted)
• Flash Point: 92.7°C
• PSA: 40.46000
• Density: 1.391g/cm³
• LogP: 2.23850
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 174.068079557
• Heavy Atom Count: 13
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C3=C(C=CC(=C23)O)O

Technology Process of 1,4-Dihydro-1,4-methano-5,8-naphthalenediol

There total 12 articles about 1,4-Dihydro-1,4-methano-5,8-naphthalenediol 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: 100.0%

1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione (54353-48-9,1200-89-1) → p-dihydroxybenzonorbornadiene (3090-47-9)

Guidance literature:

With silica gel; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2017.02.017

Reference yield: 92.7%

1,4,4a,6,7,8a-hexahydro-1,4-methano-naphthalene-5,8-dione (21428-54-6) → p-dihydroxybenzonorbornadiene (3090-47-9)

Guidance literature:

With sodium acetate; In methanol; at 50 ℃; for 3h; Inert atmosphere;

Reference yield: 90.0%

norbornenoquinone (51175-59-8) → p-dihydroxybenzonorbornadiene (3090-47-9)

Guidance literature:

With silica gel; In dichloromethane; at 25 ℃;

DOI:10.1080/00397919808005109

upstream raw materials:

5,8-diacetoxy-1,4-dihydro-1,4-methylenonaphthalene

norbornenoquinone

1α,4α,4aβ,10aα,5β,8β,8aα,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione

Tropone

Downstream raw materials:

8,11-dimethoxybenzonorbornadiene

(+/-)-4-nitro-benzoic acid-(3c,5,8-trimethoxy-1,2,3,4-tetrahydro-1r,4c-methano-naphthalen-2t-yl ester)

C₄₅H₅₅FN₈O₆

C₃₀H₃₂F₃N₃O₅S

Refernces

• 1、 Marchand,Alihodzic,Shukla. "A simple procedure for preparing annulated p-benzoquinones. Improved synthesis of 1,4-dihydro-1,4-methanonaphthalene-5,8-dione". . p. 541 - 546. Retrieved 1998.
• 2、 -. "BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF". Paragraph 0218; 0255; 0256; 0257. . Retrieved 2017/04/11.
• 3、 -. "BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF". . . Retrieved 2015/08/06.