143536-11-2

Basic information

• Product Name: 3-Butyne-1,2-diol, 4-phenyl-, (R)-
• CAS NO: 143536-11-2
• Molecular Formula: C10H10O2
• Molecular Weight: 162.188
• Mol File: 143536-11-2.mol

Chemical Properties

• CAS DataBase Reference: 3-Butyne-1,2-diol, 4-phenyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butyne-1,2-diol, 4-phenyl-, (R)-(143536-11-2)
• EPA Substance Registry System: 3-Butyne-1,2-diol, 4-phenyl-, (R)-(143536-11-2)

Safety Data

• Hazardous Substances Data: 143536-11-2(Hazardous Substances Data)

Upstream product

• 13633-26-6 4-phenylbut-1-en-3-yne 
• 1219685-01-4 C₁₀H₈O₂ 
• 64-17-5 ethanol 
• 2327-22-2 2-oxo-4-phenyl-3-butynoic acid methyl ester 
• 1619-73-4 ethyl 2-oxo-4-phenylbut-3-ynoate 
• 536-74-3 phenylacetylene 
• 17451-20-6 (E)-ethyl-2-oxo-4-phenylbut-3-enoate 

Downstream Products

• 1173898-33-3 4-(phenylethynyl)-1,3-dioxolan-2-one 
• 17113-33-6 2-phenylfuran 
• 637-44-5 phenylpropyolic acid 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 591218-65-4 (S)-4-phenylbut-3-yne-1,2-diol 
• 1391757-77-9 1-(3-phenylquinoxalin-2-yl)ethane-1,2-diol 
• 1370340-02-5 3,4-dihydroxy-1-phenylbutane-1,2-dione 

Relevant articles and documents

A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentanedione (DPD) and related compounds as potential modulators of bacterial quorum sensing

Resistance to antibiotics is an increasingly serious threat to global public health and its management translates to significant health care costs. The validation of new Gram-negative antibacterial targets as sources for potential new antibiotics remains a challenge for all the scientists working in this field. The interference with bacterial Quorum Sensing (QS) mechanisms represents a potentially interesting approach to control bacterial growth and pursue the next generation of antimicrobials. In this context, our research is focused on the discovery of novel compounds structurally related to (S)-4,5-dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule able to modulate bacterial QS in both Gram-negative and Gram-positive bacteria. In this study, a practical and versatile synthesis of racemic DPD is presented. Compared to previously reported syntheses, the proposed strategy is short and robust: it requires only one purification step and avoids the use of expensive or hazardous starting materials as well as the use of specific equipment. It is therefore well suited to the synthesis of derivatives for pharmaceutical research, as demonstrated by four series of novel DPD-related compounds described herein.

Synthesis of Alkynyl-Glycinols by Lewis Acid Catalyzed Propargylic Substitution of Bis-Imidates

Racemic and enantioenriched alkynyl-glycinols can be synthesized by Lewis acid catalyzed cyclization reaction of bis-trichloracetimidates derived from alkynyl-glycols. The cyclization proceeds selectively to give 4-alkynyl-oxazolines as the propargylic substitution products. Enantioenriched bis-imidates that contain an alkyl or trimethylsilyl substituent at the acetylene gave oxazolines with complete inversion of configuration. In turn, considerable racemization was observed in the cyclization of bis-imidates that contain a phenyl substituent. The racemization for these substrates can be suppressed by introduction of the electronegative substituent at the phenyl ring. Oxazolines prepared by bis-imidate cyclization reaction can be readily transformed to protected alkynyl-glycol derivatives. Racemic and enantioenriched alkynyl-glycinol derivatives can be synthesized by Lewis acid catalyzed cyclization reaction of bis-trichloroacetimidates into oxazolines.

Leveraging the micellar effect: Gold-catalyzed dehydrative cyclizations in water at room temperature

The first examples of gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles in an aqueous medium are presented. These reactions take place within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. By the addition of simple salts such as sodium chloride, reaction times and catalyst loadings can be significantly decreased.

Utilization of whole cell mediated deracemization in a chemoenzymatic synthesis of enantiomerically enriched polycyclic chromeno[4,3-b] pyrrolidines

Various aryl and alkyl substituted optically pure propargyl alcohols were obtained with excellent ee (up to >99%) and isolated yields (up to 87%) by deracemization using whole cells of Candida parapsilosis ATCC 7330. The whole cells show substrate specificity towards alkyl substituted propargyl alcohols and a switch in the enantioselectivity has been observed from 'R' to 'S' upon increasing the chain length. For the first time, enantiopure (R)-4-(3-hydroxybut-1-ynyl)benzonitrile, (R)-4-(biphenyl-4-yl)but-3-yn-2-ol, (S)-ethyl 3-hydroxy-5-phenylpent-4-ynoate and (S)-4-phenylbut-3-yne-1,2-diol were obtained using this strategy. Optically pure propargyl alcohol thus obtained was used as a chiral starting material in the synthesis of enantiomerically enriched poly-substituted pyrrolidines and a pyrrole derivative successfully demonstrating a chemoenzymatic route. This journal is

Stereochemical preference of Candida parapsilosis ATCC 7330 mediated deracemization: E- versus Z-aryl secondary alcohols

The stereochemical preference of the biocatalyst, Candida parapsilosis ATCC 7330, was investigated with respect to the E/Z configuration in the deracemization and the asymmetric reduction of aryl secondary alcohols and prochiral ketones, respectively. The

Chemoselective reduction and transesterification of α-keto propargylic esters mediated by NaBH4 and CeCl37H 2O

An efficient one-pot synthesis of α-hydroxy propargylic esters by chemoselective reduction followed by transesterification using NaBH4 in combination with CeCl37H2O is described.

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols

Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargyllc alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles In minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.

Synthesis of α-hydroxyallenes by copper-catalyzed S N2′substitution of propargylic dioxolanones

A new catalytic method for the synthesis of α-hydroxyallenes is described. Efficient SN2′ substitution of propargylic dioxolanones has been achieved with a copper(I)/P(OBu)3 catalyst: using Grignard reagents as the nucleophiles. The

Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: A practical route to furans and pyrroles

The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amlno-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph 3P)AuCl - AgNTf2 or (Ph3P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles In excellent yields (85-98% yields). This method Is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.

Asymmetric dihydroxylation of enynes

Catalytic asymmetric dihydroxylations of 1,3-enynes were studied using 9-0-(9′-phenanthryl) dihydroquinidine (PHN-DHQD) 1 and 1,4-bis-(9-0-dihydroquinidine) phthalazine (DHQD2-PHAL) 2. Terminal olefins showed moderate (38-79% ee) and trans-disu