Celaphal A

Base Information

• Chemical Name: Celaphal A
• CAS No.: 244204-40-8
• Molecular Formula: C₁₇H₂₀O₄
• Molecular Weight: 288.343
• Mol file: 244204-40-8.mol

Synonyms:(+)-CelaphanolA; Celaphanol A

Chemical Property of Celaphal A

Chemical Property:

• Boiling Point: 532.9±50.0 °C(Predicted)
• PKA: 7.60±0.60(Predicted)
• PSA: 77.76000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 3.57400

Purity/Quality:

98%min ^*data from raw suppliers

CelaphanolA 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Celaphanol A (also known as (+)-Celaphanol A or Celaphanol A) is a diterpene derived from *Celastrus stephanotifolius*, notable for its biological activities and medicinal significance. Its synthesis was achieved via a six-step route involving key transformations such as intramolecular cyclization and enolization, culminating in an efficient and scalable method to produce Celaphal A for further pharmacological exploration.

Technology Process of Celaphal A

There total 7 articles about Celaphal A 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: 85.0%

(+/-)-2,3,4,4a-tetrahydro-10-hydroxy-6,7-dimethoxy-1,1,4a-trimethyl-9(1H)-phenanthrenone (477217-39-3) → (+/-)-celaphanol A (244204-40-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1002/jccs.200200089

Reference yield:

α-cyclocitral (14505-74-9,41721-03-3,59462-59-8,432-24-6) → (+/-)-celaphanol A (244204-40-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / diethyl ether / 2 h / Heating

2: 85 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / 20 °C

3: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / 20 °C

4: 90 percent / CrO₃; acetic acid / 0.5 h / 20 °C

5: 80 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 20 °C

6: 85 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

With chromium(VI) oxide; boron trifluoride diethyl etherate; potassium tert-butylate; boron tribromide; acetic acid; pyridinium chlorochromate; In diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1002/jccs.200200089

Reference yield:

3,4-dimethoxyphenylmethylmagnesium chloride (108071-30-3) → (+/-)-celaphanol A (244204-40-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / diethyl ether / 2 h / Heating

2: 85 percent / pyridinium chlorochromate / CH₂Cl₂ / 2.5 h / 20 °C

3: 93 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / 20 °C

4: 90 percent / CrO₃; acetic acid / 0.5 h / 20 °C

5: 80 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 20 °C

6: 85 percent / BBr₃ / CH₂Cl₂ / 0.5 h / 0 °C

With chromium(VI) oxide; boron trifluoride diethyl etherate; potassium tert-butylate; boron tribromide; acetic acid; pyridinium chlorochromate; In diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1002/jccs.200200089

upstream raw materials:

(+/-)-2,3,4,4a-tetrahydro-10-hydroxy-6,7-dimethoxy-1,1,4a-trimethyl-9(1H)-phenanthrenone

α-cyclocitral

3,4-dimethoxyphenylmethylmagnesium chloride

(cis)-1,2,3,4,4a,10a-hexahydro-6,7-dimethoxy-1,1,4a-trimethyl-9,10-phenanthrenedione

Refernces

First total synthesis of (±)-celaphanol A

10.1002/jccs.200200089

The research presents the first total synthesis of (±)-Celaphanol A, a diterpene isolated from the stems of Celastrus stephanotifolius, which has garnered interest due to its biological activities and traditional medicinal uses. The purpose of this study was to develop a synthetic route for this compound to further investigate its structure-activity relationships and expand the synthesis of diterpenoids. The synthesis was achieved through a six-step process starting from α-cyclocitral and 3,4-dimethoxybenzyl chloride. Key steps included intramolecular cyclization with BF3·Et2O and enolization in t-BuOK/t-BuOH, yielding an all-cis isomer intermediate crucial for the synthesis of aromatic tricyclic diterpenes. The final product, (±)-Celaphanol A, was obtained in 85% yield after demethylation with BBr3. The study concluded that a simple and efficient synthetic route had been successfully developed, providing a foundation for further research on the biological activities and potential applications of this diterpene.

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