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Chemical Structure| 556-82-1 Chemical Structure| 556-82-1
Chemical Structure| 556-82-1

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3-Methyl-2-buten-1-ol is a naturally occurring endogenous metabolite found in pine trees, and it is commonly used as a fragrance component in cosmetics and detergents.

Synonyms: Prenol; Prenyl alcohol; Dimethylallyl alcohol

4.5 *For Research Use Only !

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Product Citations

Product Citations

Gardner, Eric D. ; Dimas, Dustin A. ; Finneran, Matthew C. ; Brown, Sara M. ; Burgett, Anthony W. ; Singh, Shanteri

Abstract: Tryprostatin A and B are prenylated, tryptophan-containing, diketopiperazine natural products, displaying cytotoxic activity through different mechanisms of action. The presence of the 6-methoxy substituent on the indole moiety of tryprostatin A was shown to be essential for the dual inhibition of topoisomerase II and tubulin polymerization However, the inability to perform late-stage modification of the indole ring has limited the structure-activity relationship studies of this class of natural products. Herein, we describe an efficient chemoenzymic approach for the late-stage modification of tryprostatin B using a cyclic dipeptide N-prenyltransferase (CdpNPT) from Aspergillus fumigatus, which generates novel analogs functionalized with allylic, benzylic, heterocyclic, and diene moieties. Notably, this biocatalytic functionalizational study revealed high selectivity for the indole C6 position. Seven of the 11 structurally characterized analogs were exclusively C6-alkylated, and the remaining four contained predominant C6-regioisomers. Of the 24 accepted substrates, 10 provided >50% conversion and eight provided 20-50% conversion, with the remaining six giving <20% conversion under standard conditions. This study demonstrates that prenyltransferase-based late-stage diversification enables direct access to previously inaccessible natural product analogs.

Keywords: biocatalysts ; chemoenzymatic synthesis ; late-stage functionalization ; prenyltransferase ; tryprostatin

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Alternative Products

Product Details of 3-Methyl-2-buten-1-ol

CAS No. :556-82-1
Formula : C5H10O
M.W : 86.13
SMILES Code : CC(C)=CCO
Synonyms :
Prenol; Prenyl alcohol; Dimethylallyl alcohol
MDL No. :MFCD00002916
InChI Key :ASUAYTHWZCLXAN-UHFFFAOYSA-N
Pubchem ID :11173

Safety of 3-Methyl-2-buten-1-ol

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H302+H332-H313-H314-H335-H402
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P370+P378-P403+P233-P403+P235-P405-P501
Class:8(3)
UN#:2920
Packing Group:

Application In Synthesis of 3-Methyl-2-buten-1-ol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 556-82-1 ]

[ 556-82-1 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 347-84-2 ]
  • [ 556-82-1 ]
  • 6-(4-fluorophenyl)-2,2-dimethyl-5-phenyl-3,4-dihydro-2H-pyran [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% General procedure: Fe(OTf)3 (3c, 15 mg, 0.03 mmol) was added to a solution of deoxybenzoins 6 (1.0 mmol) and prenyl alcohol (2, 90 mg, 1.05 mmol) in MeNO2 (5 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. The reaction mixture was stirred at reflux for 20 h. The reaction mixture was cooled to rt and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=8/1-4/1) afforded 7.
  • 3
  • [ 3027-21-2 ]
  • [ 556-82-1 ]
  • (methoxy)(3-methyl-2-butenoxy)(methyl)(phenyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.3% With CBV780; at 23℃; for 0.0833333h;Microwave irradiation; 10096] A mixture of 1.65 mmol of <strong>[3027-21-2]methylphenyldi(methoxy)silane</strong> (Ia), 6.6 mmol of butanol (ha) and 5 mg of CBV 780 (by Zeolyst International) was charged into a reaction tube, with stirring for 1 minute at room temperature (23° C.). The resulting product was analyzed using a gas chromatograph and a gas chromatographlmass spectrometer. The results revealed that a mixture of butoxysilane (lila) (lila-i:methylphenyl(methoxy)(butoxy)silane and IIIa-2: methylphenyldi(butoxy)silane, lila-i :IIIa-2=90: 10) had been generated with a yield of 88.5percent (see Table 1).10097] Reactions and analyses were carried out in the sameway as in Example 1, but modi1,?ing reaction conditions(starting materials, catalysts, temperature, time and so forth).The results of measurements of product yields are given inTable 1.
With CBV 780; at 23℃; for 0.0833333h;Microwave irradiation; General procedure: di(methoxy)(methyl)(phenyl) silane (IIIa) 1.6mmol, 2-methoxyethanol (IVa) 3.2mmol, CBV780 (Zeolyst Co., Ltd.) 5 mg of the mixture in the reaction tube, 10 minutes at room temperature (25 °C ). An analysis result of a product gas chromatograph (GC), gas chromatograph/mass spectrometer (GC-MS), in nuclear magnetic resonance spectrum analyzer (NMR)and, as a product, di(2-methoxyethoxy)silane(phenyl)(methyl) (Va-2) (= (Ia-1) alkoxysilanes of partially substd. (methoxyacetic) (2-methoxyethoxy) (methyl)(phenylpropionic) silane (Va- 1) (=Ia-1) and generates a total substd. alkylalkoxy silane yield (Va-1: Va-2 = 74:26)of total 68percent, (refer to Table 1) in the part substituted alkoxysilane substd. (Ia-1) 12 50percent of the yield.
 

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