(+/-)-zizaene

Base Information

• Chemical Name: (+/-)-zizaene
• CAS No.: 35946-04-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.356
• Mol file: 35946-04-4.mol

Synonyms:

Chemical Property of (+/-)-zizaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-zizaene

There total 25 articles about (+/-)-zizaene 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: 64.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1RS,2RS,5RS,8SR)-2,7,7-trimethyltricyclo[6.2.1.01,5]undecan-6-one → (+/-)-zizaene (18444-94-5,22387-81-1,33043-21-9,35946-04-4,35946-05-5,42577-13-9)

Guidance literature:

With potassium 2-methylbutan-2-olate; In toluene; at 90 - 92 ℃; for 6h;

DOI:10.1016/S0040-4020(02)00063-7

Reference yield:

(+/-)-13-Thiophenylzizan-6-yl-benzoat (38230-37-4) → (+/-)-zizaene (18444-94-5,22387-81-1,33043-21-9,35946-04-4,35946-05-5,42577-13-9)

Guidance literature:

With ammonia; lithium; In pentane;

DOI:10.1021/ja00768a069

Reference yield:

5-methoxy-3,3-dimethyl-indan-1-one (60812-53-5) → (+/-)-zizaene (18444-94-5,22387-81-1,33043-21-9,35946-04-4,35946-05-5,42577-13-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 73 percent / diisopropylamine; BuLi / tetrahydrofuran; hexane / 15 h / -10 - 20 °C

2: 92 percent / KOH / methanol; H₂O / 6 h / Heating

3: NaBH₄; NaOH / H₂O / 24 h / 20 °C

4: H₂; HClO₄ / 10 percent Pd-C / acetic acid / 1 h

5: 94 percent / diethyl ether / 0 °C

6: 95 percent / LiAlH₄ / diethyl ether / 4 h / Heating

7: 80 percent / CBr₄; Ph₃P / diethyl ether / 5 h / 25 °C

8: 92 percent / BBr₃ / CH₂Cl₂ / 17 h / 0 - 20 °C

9: 73 percent / t-BuOK / 2-methyl-propan-2-ol / 10 h / 80 °C

10: 85 percent / CuI / diethyl ether / 2 h / 0 °C

11: 94 percent / BF₃*Et₂O / methanol / 20 h / 20 °C

12: 86 percent / Na / liquid ammonia; ethanol

13: 85 percent / OsO₄ / pyridine / 120 h / 20 °C

14: 90 percent / pyridine / 15 h / 20 °C

15: 88 percent / t-BuOK / 2-methyl-propan-2-ol / 0.17 h / 20 °C

16: 64 percent / potassium tert-amylate / toluene / 6 h / 90 - 92 °C

With potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; carbon tetrabromide; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; sodium; boron tribromide; potassium 2-methylbutan-2-olate; diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; ammonia; water; acetic acid; toluene; tert-butyl alcohol; 16: Wittig olefination;

DOI:10.1016/S0040-4020(02)00063-7

upstream raw materials:

(+/-)-13-Thiophenylzizan-6-yl-benzoat

Methyltriphenylphosphonium bromide

5-methoxy-3,3-dimethyl-indan-1-one

7,7-dimethyltricyclo<6.2.1.0^1.6>undeca-2,5-dien-4-one