3-Penten-1-ol, (3E)-

• CAS: 764-37-4
• Catalog Number: ACM764374-1
• Category: Main Products
• Molecular Weight: 86.13g/mol
• Molecular Formula: C5H10O
• Synonyms: 3-Penten-1-ol, (3E)-;(E)-Pent-3-en-1-ol;764-37-4;3-Penten-1-ol;trans-3-Pentenol-1;3-pentenol;pent-3-en-1-ol;39161-19-8;3-Penten-1-ol, (E)-;EINECS 212-118-1;(E)-3-Penten-1-ol;(3E)-3-Penten-1-ol;TRANS-3-PENTEN-1-OL;DTXSID30883565;764-38-5;ZINC1845733;AKOS006282973
• IUPAC Name: (E)-pent-3-en-1-ol
• SMILES: CC=CCCO
• InChI: InChI=1S/C5H10O/c1-2-3-4-5-6/h2-3,6H,4-5H2,1H3/b3-2+
• InChI Key: FSUXYWPILZJGCC-NSCUHMNNSA-N
• Boiling Point: 118 - 119 °C
• Appearance: Colorless clear liquid
• Complexity: 39.2
• Covalently-Bonded Unit Count: 1
• EC Number: 212-119-7;212-118-1;609-614-9
• Exact Mass: 86.073164938g/mol
• Heavy Atom Count: 6
• Hydrogen Bond Acceptor Count: 1
• Monoisotopic Mass: 86.073164938g/mol
• Rotatable Bond Count: 2
• Topological Polar Surface Area: 20.2Ų
• XLogP3: 0.9

Case Study

(E)-3-Penten-1-ol as Key Intermediate for Stereoselective Thiol Acetate Synthesis

Dai, Yifeng, et al. Journal of Chemical Research 38.4 (2014): 236-239.

This work demonstrated the utility of (E)-3-penten-1-ol as a versatile precursor for synthesizing stereodefined cis- and trans-2-methyltetrahydrofuran-3-thiol acetates, with evaluation of olfactory properties.
Synthesis Routes from (E)-3-Penten-1-Ol:
· Synthesis of trans-2-Methyl-3-hydroxytetrahydrofuran: (E)-3-Penten-1-ol was first converted to its mesylate derivative, which underwent epoxidation with H2O2/HCOOH followed by NaOH-mediated ring closure to yield trans-2-methyl-3-hydroxytetrahydrofuran in 78% overall yield. Direct epoxidation without mesylation gave lower yield (59%).
· Conversion to cis-2-Methyltetrahydrofuran-3-thiol Acetate: The trans-hydroxy intermediate was transformed via two routes: 1) Mesylation with MsCl (89% yield) followed by SN2 substitution with AcSH (81% yield, ~72% overall); or 2) Direct Mitsunobu reaction with AcSH/DIAD/Ph3P (65% yield). Both routes produced identical cis-configured products confirmed by ¹H NMR.
· Synthesis of trans-2-Methyltetrahydrofuran-3-thiol Acetate: (E)-3-Penten-1-ol mesylate was oxidized with KMnO4 to form cis-2-methyl-3-hydroxytetrahydrofuran, which was subsequently mesylated and underwent SN2 substitution with AcSH to yield the trans-configured thiol acetate.

Custom Q&A

What is the molecular formula of Oxy-3-pentene?

The molecular formula of Oxy-3-pentene is C5H10O.

What is the molecular weight of Oxy-3-pentene?

The molecular weight of Oxy-3-pentene is 86.13 g/mol.

What is the IUPAC name of Oxy-3-pentene?

The IUPAC name of Oxy-3-pentene is (E)-pent-3-en-1-ol.

What is the InChI of Oxy-3-pentene?

The InChI of Oxy-3-pentene is InChI=1S/C5H10O/c1-2-3-4-5-6/h2-3,6H,4-5H2,1H3/b3-2+.

What is the InChIKey of Oxy-3-pentene?

The InChIKey of Oxy-3-pentene is FSUXYWPILZJGCC-NSCUHMNNSA-N.

What is the canonical SMILES of Oxy-3-pentene?

The canonical SMILES of Oxy-3-pentene is CC=CCCO.

What is the isomeric SMILES of Oxy-3-pentene?

The isomeric SMILES of Oxy-3-pentene is C/C=C/CCO.

What is the CAS number of Oxy-3-pentene?

The CAS number of Oxy-3-pentene is 764-37-4.

What is the XLogP3-AA value of Oxy-3-pentene?

The XLogP3-AA value of Oxy-3-pentene is 0.9.

What is the hydrogen bond donor count of Oxy-3-pentene?

The hydrogen bond donor count of Oxy-3-pentene is 1.