Estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride

Base Information

• Chemical Name: Estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride
• CAS No.: 148259-10-3
• Molecular Formula: C₁₈H₂₁ClO₃S
• Molecular Weight: 352.882
• DSSTox Substance ID: DTXSID30933352
• Nikkaji Number: J617.454J
• Mol file: 148259-10-3.mol

Synonyms:1,3,5-ETO-17-OSCl;estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride

Chemical Property of Estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride

Chemical Property:

• Boiling Point: 489.2±45.0 °C(Predicted)
• PSA: 59.59000
• Density: 1.305±0.06 g/cm3(Predicted)
• LogP: 5.12010
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 352.0899934
• Heavy Atom Count: 23
• Complexity: 610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=C3C=CC(=C4)S(=O)(=O)Cl
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)S(=O)(=O)Cl

Technology Process of Estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride

There total 3 articles about Estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride 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: 55.0%

3-(benzylthio)estra-1,3,5(10)-trien-17-one (1670-28-6) → estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride (148259-10-3)

Guidance literature:

With chlorine; acetic acid; In water; for 0.0833333h;

DOI:10.1016/0039-128X(93)90045-O

Reference yield:

sodium S-(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl sulfothioate → estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride (148259-10-3)

Guidance literature:

With tert-butylhypochlorite; water; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1039/c4cc09633a

Reference yield:

estrone triflate (92817-04-4) → estra-1,3,5(10)-trien-17-one-3-sulfonyl chloride (148259-10-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; XPhos; caesium carbonate; Sodium thiosulfate pentahydrate; water / tert-butyl alcohol; toluene / 8 h / 80 °C / Inert atmosphere

2: water; tert-butylhypochlorite / acetonitrile / 0.5 h / 0 °C

With Sodium thiosulfate pentahydrate; tert-butylhypochlorite; water; palladium diacetate; caesium carbonate; XPhos; In toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1039/c4cc09633a

upstream raw materials:

3-(benzylthio)estra-1,3,5⁽¹⁰⁾-trien-17-one

estrone triflate

Refernces

• 1、 Li, Pui-Kai,Pillai, Radhakrishnan,Young, Barry L.,Bender, William H.,Martino, Dino M.,Lin, Fu-Tyan. "Synthesis and biochemical studies of estrone sulfatase inhibitors". . p. 106 - 111. Retrieved 2007/10/02.