(R)-3-Hydroxy-4-pentenenitrile

Base Information

• Chemical Name: (R)-3-Hydroxy-4-pentenenitrile
• CAS No.: 7451-85-6
• Molecular Formula: C5H7NO
• DSSTox Substance ID: DTXSID901303474
• Nikkaji Number: J932.447J
• Mol file: 7451-85-6.mol

Synonyms:3-hydroxypent-4-ene nitrile;(R)-3-Hydroxy-4-pentenenitrile;CHEBI:183221;DTXSID901303474;(3R)-3-Hydroxy-4-pentenenitrile;7451-85-6

Chemical Property of (R)-3-Hydroxy-4-pentenenitrile

Chemical Property:

• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 97.052763847
• Heavy Atom Count: 7
• Complexity: 99.9

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC(CC#N)O
• Isomeric SMILES: C=C[C@@H](CC#N)O

Technology Process of (R)-3-Hydroxy-4-pentenenitrile

There total 6 articles about (R)-3-Hydroxy-4-pentenenitrile 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: 79.0%

(R)-5-((4-methoxybenzyl)oxy)hept-6-enenitrile → (R)-3-hydroxy-4-pentenenitrile (6071-81-4,27451-36-1,7451-85-6)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 3h; enantioselective reaction;

DOI:10.1002/anie.201603538

Reference yield:

(RS)-3-hydroxypent-4-enenitrile (27451-36-1) → (2S)-1-cyano-2-hydroxy-3-butene (6071-81-4) + (R)-3-hydroxy-4-pentenenitrile (6071-81-4,27451-36-1,7451-85-6) + (S)-3-hydroxy-4-pentenoic acid (38996-05-3) + (R)-3-hydroxy-4-pentenoic acid (38996-04-2)

Guidance literature:

With Rhodococcus erythropolis SET₁ cells; In aq. phosphate buffer; at 25 ℃; for 48h; pH=7; enantioselective reaction; Microbiological reaction;

DOI:10.1002/ejoc.201403201

Reference yield:

epoxybutene (930-22-3,62249-81-4) + sodium cyanide (143-33-9,25596-52-5) → (2S)-1-cyano-2-hydroxy-3-butene (6071-81-4) + (R)-3-hydroxy-4-pentenenitrile (6071-81-4,27451-36-1,7451-85-6)

Guidance literature:

With halohydrin dehalogenase from Arthrobacter sp. AD₂ (HheA); Tris-SO₄ buffer; In dimethyl sulfoxide; at 22 ℃; for 5h; pH=7.5; Title compound not separated from byproducts;

DOI:10.1002/adsc.200505333

upstream raw materials:

3-acetoxy-pent-4-enenitrile

epoxybutene

sodium cyanide

(RS)-3-hydroxypent-4-enenitrile

Refernces

• 1、 Coady, Tracey M.,Coffey, Lee V.,O'Reilly, Catherine,Lennon, Claire M.. "Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure". supporting information. p. 1108 - 1116. Retrieved 2015/02/19.
• 2、 Itoh, Toshiyuki,Mitsukura, Koichi,Kanphai, Wipa,Takagi, Yumiko,Kihara, Hiroshi,Tsukube, Hiroshi. "Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis". . p. 9165 - 9172. Retrieved 2007/10/03.