Zephyranthine

Base Information

• Chemical Name: Zephyranthine
• CAS No.: 2030-55-9
• Molecular Formula: C₁₆H₁₉NO₄
• Molecular Weight: 289.331
• Nikkaji Number: J2.125.858J
• Wikidata: Q105287276
• Mol file: 2030-55-9.mol

Synonyms:zephyranthine

Chemical Property of Zephyranthine

Chemical Property:

• Vapor Pressure: 2.82E-09mmHg at 25°C
• Boiling Point: 460.5°Cat760mmHg
• Flash Point: 232.3°C
• PSA: 62.16000
• Density: 1.48g/cm³
• LogP: 0.76640
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 289.13140809
• Heavy Atom Count: 21
• Complexity: 433

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC3=CC4=C(C=C3C5C2C1CC(C5O)O)OCO4
• Isomeric SMILES: C1CN2CC3=CC4=C(C=C3[C@H]5[C@H]2[C@H]1C[C@H]([C@H]5O)O)OCO4
• Description: This alkaloid occurs in Zephyranthes candida and forms colourless crystals from EtOH. It is laevorotatory with [α]24/sup>D - 43.17° (c 0.47, CHCI3 ). Among the crystalline salts and derivatives that have been prepared are the monoacetate which forms a hydrochloride, m.p. 24 7-8°C; the diacetate, m.p. 68-700 C; picrate, m.p. 194-5°C; methiodide, m.p. 294-5°C and the isopropylidene derivative, m.p. 156-7"C.

Technology Process of Zephyranthine

There total 71 articles about Zephyranthine 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: 80.0%

lycorine (476-28-8,6835-91-2,19312-40-4,66816-51-1) → dihydrolycorine (2030-55-9,6271-21-2,21851-15-0,30074-34-1,84236-20-4,89577-34-4,31387-87-8)

Guidance literature:

With hydrogen; platinum on activated charcoal; In acetic acid; under 1471.02 Torr; Ambient temperature;

DOI:10.1016/S0031-9422(00)80145-4

Reference yield: 79.0%

C16H17NO5 → (-)-zephyranthine (2030-55-9,31387-87-8)

Guidance literature:

With borane-THF; In tetrahydrofuran;

DOI:10.3987/COM-18-S(F)40

Reference yield: 62.0%

(1S,2R,3aR,3a1R,12bS)-1,2-dihydroxy-1,2,3,3a,3a1,4,5,12b-octahydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one → (-)-zephyranthine (2030-55-9,31387-87-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Reflux;

DOI:10.1002/asia.201700555

upstream raw materials:

1α-acetoxy-9,10-methylenedioxy-galanthan-2-one

tetrahydrofuran

(3aS,3a¹R,12bS)-3,3a,3a¹,4,5,12b-hexahydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7-one

(S)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)pent-4-en-1-ol

Downstream raw materials:

9,10-methanediyldioxy-2α-(toluene-4-sulfonyloxy)-galanthan-1α-ol

Refernces

• 1、 Wildman,Kaufman. "-". . p. 5815. Retrieved 1954.
• 2、 Chen, Jingbo,Ma, Guolan,Wei, Qi,Yang, Shaoxiong,Zeng, Xiaoyu,Zhang, Hongbin,Zhao, Yuxiang,Zhu, Yanren. "Short, enantioselective, gram-scale synthesis of (?)-zephyranthine". . p. 9452 - 9457. Retrieved 2021/07/25.
• 3、 Ishii, Koki,Seki-Yoritate, Yuna,Ishibashi, Mizuki,Liaw, Ming Wai,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka. "Total synthesis of (–)-zephyranthine". . p. 111 - 117. Retrieved 2019/06/24.