6999-19-5 Usage
Description
4-TRIMETHYLSILYL-3-BUTYN-2-OL, also known as 4-TMS-3-butyn-2-ol, is a colorless liquid with a boiling point of 83-85°C at 13 mmHg. It is an organic compound featuring a trimethylsilyl group, a butyn-2-ol group, and a triple bond, which makes it a versatile building block in organic synthesis.
Uses
Used in Pharmaceutical Industry:
4-TRIMETHYLSILYL-3-BUTYN-2-OL is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows for the creation of complex molecules with potential therapeutic applications.
Used in Organic Synthesis:
4-TRIMETHYLSILYL-3-BUTYN-2-OL is used as a versatile building block in organic synthesis for the development of new compounds with diverse applications, including pharmaceuticals, agrochemicals, and materials science.
Used in the Synthesis of Branimycin:
More recently, Mulzer has reported the use of the corresponding allenylsilane derived from 4-TMS-3-butyn-2-ol for use in the synthesis of the C13–C18 fragment of branimycin. This highlights the compound's utility in the synthesis of complex natural products with potential biological activities.
Preparation
racemic 4-trimethylsilyl-3-butyn-2-ol can
be prepared by deprotonation with strong bases (BuLi, LDA,
Grignards reagents) of trimethylsilylacetylene followed
by addition to acetaldehyde.Deprotonation of 3-butyn-2-
ol followed by quenching with excess trimethylsilyl chloride
followed by concomitant hydrolysis of the trimethylsilyl ether
is generally the most straightforward route.Enzymatic reduction
of 4-TMS-3-butyn-2-one has also been used to prepare the
reagent using alcohol dehydrogenase.Preparation of nonracemic 4-TMS-3-butyn-2-ol has been
accomplished by asymmetric addition of dimethylzinc to
acetaldehyde promoted by TADDOL or addition of a
trimethylsilylvinylsulfoxide to acetaldehyde followed by thermal
elimination of the sulfoxide.Asymmetric reduction of 4-
TMS-3-butyn-2-one using stoichiometric reducing reagents,
catalytic transfer hydrodrogenation,and enzymatic reduction
with isolated protein or whole cells afford the 4-TMS-3-butyn-
2-ol with varying degrees of enantioenrichment.Enzymatic resolution by esterification of the racemic alcohol is the method
of choice for the large-scale preparation.
Check Digit Verification of cas no
The CAS Registry Mumber 6999-19-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,9 and 9 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 6999-19:
(6*6)+(5*9)+(4*9)+(3*9)+(2*1)+(1*9)=155
155 % 10 = 5
So 6999-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H14OSi/c1-7(8)5-6-9(2,3)4/h7-8H,1-4H3
6999-19-5Relevant articles and documents
Propargylation of CoQ0 through the Redox Chain Reaction
Pawlowski, Robert,Stodulski, MacIej,Mlynarski, Jacek
, p. 683 - 692 (2022/01/04)
An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.
Towards the Total Synthesis of Jerangolids – Synthesis of an Advanced Intermediate for the Pharmacophore Substructure
Huch, Volker,Hutter, Michael,Jauch, Johann,Lenhof, Julian
, p. 5833 - 5840 (2020/09/22)
The jerangolids are a class of natural products with a skipped diene substructure isolated from Sorangium cellulosum. Here, we present a new strategy for the total synthesis of these compounds based on a skipped diyne as central building block and a suitably substituted epoxy aldehyde as building block for the dihydropyran substructure. So far, we reached an advanced intermediate which is related to the pharmacophore subunit of the jerangolids as well as of the ambruticins. A key step is a Shi epoxidation with high e.r. to form the epoxy aldehyde. Both building blocks are coupled in a Carreira alkynylation, where additional mechanistic studies based on DFT calculation were realized. The alkynylation is followed by a nucleophilic 6-endo-tet epoxide opening to form the pyran structure and a Nicholas reduction to remove a propargylic OH group.
Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition
Zhang, Yanshun,Sun, Yaoliang,Wei, Yin,Shi, Min
supporting information, p. 2129 - 2135 (2019/03/13)
A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).