Hex-2-ene-1,6-diol

Base Information

• Chemical Name: Hex-2-ene-1,6-diol
• CAS No.: 63974-05-0
• Molecular Formula: C6H12O2
• Molecular Weight: 116.16
• DSSTox Substance ID: DTXSID30710125
• Mol file: 63974-05-0.mol

Synonyms:hex-2-ene-1,6-diol;63974-05-0;DTXSID30710125

Chemical Property of Hex-2-ene-1,6-diol

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 116.083729621
• Heavy Atom Count: 8
• Complexity: 59.5

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CC=CCO)CO

Technology Process of Hex-2-ene-1,6-diol

There total 5 articles about Hex-2-ene-1,6-diol 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%

(E)-ethyl 6-((tert-butyldimethylsilyl)oxy)hex-2-enoate (193948-52-6) → (E)-hex-2-ene-1,6-diol (63974-05-0)

Guidance literature:

(E)-ethyl 6-((tert-butyldimethylsilyl)oxy)hex-2-enoate; With diisobutylaluminium hydride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In methanol; water; at 25 - 28 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201100772

Reference yield: 46.0%

6,8-dioxa-bicyclo[3.2.1]oct-2-ene (27925-22-0) → 5-Hexen-1-ol (821-41-0) + (E)-hex-2-ene-1,6-diol (63974-05-0) + hex-4-en-1-ol (6126-50-7,928-91-6,928-92-7)

Guidance literature:

With lithium aluminium tetrahydride; In 1,2-dimethoxyethane; for 150h; Heating;

Reference yield:

(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol (98897-64-4) → (E)-hex-2-ene-1,6-diol (63974-05-0)

Guidance literature:

With hydrogenchloride; water; In methanol; for 1h;

DOI:10.1002/anie.200904671

upstream raw materials:

hex-2-yne-1,6-diol

6,8-dioxa-bicyclo[3.2.1]oct-2-ene

(E)-6-[(tert-butyldimethylsilyl)oxy]-2-hexen-1-ol

(E)-ethyl 6-((tert-butyldimethylsilyl)oxy)hex-2-enoate

Downstream raw materials:

(S)-2-vinyltetrahydrofuran

(R)-2-vinyltetrahydrofuran

2-vinyltetrahydrofuran

1-chloro-nonadec-4t-ene-7,10,13-triyne

Refernces

• 1、 Miyata, Kengo,Kutsuna, Hironori,Kawakami, Sho,Kitamura, Masato. "A chiral bidentate sp2-N ligand, naph-diPIM: Application to CpRu-catalyzed asymmetric dehydrative C-, N-, and O-allylation". supporting information; scheme or table. p. 4649 - 4653. Retrieved 2011/06/27.
• 2、 Majumdar, K. C.,Ranganayakulu, K.,Brown, R. K.. "Reactions of 6,8-Dioxabicyclo(3.2.1)oct-3-ene and 6,8-Dioxabicyclo(3.2.1)oct-2-ene with Lithium Aluminium Hydride". . p. 303 - 306. Retrieved 2007/10/02.