(5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol

Base Information

• Chemical Name: (5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol
• CAS No.: 156458-91-2
• Molecular Formula: C18H17BrO
• Molecular Weight: 329.23098
• DSSTox Substance ID: DTXSID40439774
• Mol file: 156458-91-2.mol

Synonyms:156458-91-2;(5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol;(2Z)-2-(3-Bromopropylidene)tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol;FT-0663857;(Z)-(+/-)-5-(3-Bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol;DTXSID40439774

Chemical Property of (5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol

Chemical Property:

• Boiling Point: 482.4±33.0 °C(Predicted)
• PKA: 13.87±0.20(Predicted)
• PSA: 20.23000
• Density: 1.445±0.06 g/cm3(Predicted)
• LogP: 4.49280
• Solubility.: Chloroform
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 328.04628
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

97% ^*data from raw suppliers

(5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C2=CC=CC=C2C(=CCCBr)C3=CC=CC=C31)O
• Isomeric SMILES: C1C(C2=CC=CC=C2/C(=C\CCBr)/C3=CC=CC=C31)O

Technology Process of (5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol

There total 5 articles about (5Z)-5-(3-Bromopropylidene)-5,11-dihydro-10H-dibenzo[a,d]cyclohepten-10-ol 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%

(Z)-5-γ-bromopropylidene-10,11-dihydro-10-oxo-5H-dibenzocycloheptene (156458-92-3) → 5-[3-Bromo-prop-(Z)-ylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol (156458-91-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h; Ambient temperature;

DOI:10.1080/00397919408010157

Reference yield:

10-piperidin-1-yl-dibenzo[a,d]cyclohepten-5-one (37439-92-2) → 5-[3-Bromo-prop-(Z)-ylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol (156458-91-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h

2: 100 percent / 0.1N HCl / methanol / 6 h

3: 67 percent / CBr₄, PPh₃ / CH₂Cl₂ / 2 h / 0 °C

4: 100 percent / NaBH₄ / methanol / 1 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1080/00397919408010157

Reference yield:

5-(γ-hydroxypropylidene)-(10,11-dihydro-10-oxo-5H-dibenzo)-cycloheptene (156458-89-8) → 5-[3-Bromo-prop-(Z)-ylidene]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ol (156458-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / CBr₄, PPh₃ / CH₂Cl₂ / 2 h / 0 °C

2: 100 percent / NaBH₄ / methanol / 1 h / Ambient temperature

With sodium tetrahydroborate; carbon tetrabromide; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1080/00397919408010157

upstream raw materials:

(Z)-5-γ-bromopropylidene-10,11-dihydro-10-oxo-5H-dibenzocycloheptene

10-piperidin-1-yl-dibenzo[a,d]cyclohepten-5-one

5-(γ-hydroxypropylidene)-(10,11-dihydro-10-oxo-5H-dibenzo)-cycloheptene

5-cyclopropyl-10-piperidin-1-yl-5H-dibenzo[a,d]cyclohepten-5-ol

Downstream raw materials:

(+)-(Z)-10-Hydroxy-Nortriptyline