3,3-diethoxy-but-1-yne | 132284-55-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-diethoxy-but-1-yne
• 英文别名: 3,3-Diethoxybut-1-yne
• CAS: 132284-55-0
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: WOQJTRHGKPGOMS-UHFFFAOYSA-N

物化性质

• 沸点：
  73-74 °C(Press: 60 Torr)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-叠氮基丙烷 、 3,3-diethoxy-but-1-yne 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以1.45 g的产率得到4-(diethoxymethyl)-1-isopropyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Development of Biocompatible Cu(I)‐Microdevices for Bioorthogonal Uncaging and Click Reactions

  摘要：

  Transition‐metal‐catalyzed bioorthogonal reactions emerged a decade ago as a novel strategy to implement spatiotemporal control over enzymatic functions and pharmacological interventions. The use of this methodology in experimental therapy is driven by the ambition of improving the tolerability and PK properties of clinically‐used therapeutic agents. The preclinical potential of bioorthogonal catalysis has been validated in vitro and in vivo with the in situ generation of a broad range of drugs, including cytotoxic agents, anti‐inflammatory drugs and anxiolytics. In this article, we report our investigations towards the preparation of solid‐supported Cu(I)‐microdevices and their application in bioorthogonal uncaging and click reactions. A range of ligand‐functionalized polymeric devices and off‐on Cu(I)‐sensitive sensors were developed and tested under conditions compatible with life. Last, we present a preliminary exploration of their use for the synthesis of PROTACs through CuAAC assembly of two heterofunctional mating units.

  DOI：

  10.1002/chem.202400611
• 作为产物：
  描述：

  乙醇 、 1,1,2-三溴-2-甲基环丙烷 在 sodium 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到3,3-diethoxy-but-1-yne
  参考文献：
  名称：

  Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.

  摘要：

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.

  DOI：

  10.3891/acta.chem.scand.52-1029

文献信息

• Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.
  作者：Leiv K. Sydnes、Einar Bakstad、Morten Heide、Georg W. Jensen、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0446

  日期：——

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.
• Chemistry of gem-Dihalocyclopropanes. IV. Ring Opening of gem-Dichlorocyclopropyl Ethers
  作者：Lars Skattebøl

  DOI：10.1021/jo01343a057

  日期：1966.5
• KAJIGAESHI, SHOJI;MATSUMOTO, GORO;NISHIDA, AKIKO;FUJISAKI, SHIZUO, YAMAGUTI DAJGAKU KOGAKUBU KEHNKYU XOKOKU, 40,(1989) N, S. 127-137
  作者：KAJIGAESHI, SHOJI、MATSUMOTO, GORO、NISHIDA, AKIKO、FUJISAKI, SHIZUO

  DOI：——

  日期：——
• Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.
  作者：Einar Bakstad、Leiv K. Sydnes、Anders Kjær、Salka E. Nielsen、Carl E. Olsen、Kirsi Ranta、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1029

  日期：——

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.
• Development of Biocompatible Cu(I)‐Microdevices for Bioorthogonal Uncaging and Click Reactions
  作者：Melissa van de L'Isle、Stephen Croke、Teresa Valero、Asier Unciti‐Broceta

  DOI：10.1002/chem.202400611

  日期：——

  Transition‐metal‐catalyzed bioorthogonal reactions emerged a decade ago as a novel strategy to implement spatiotemporal control over enzymatic functions and pharmacological interventions. The use of this methodology in experimental therapy is driven by the ambition of improving the tolerability and PK properties of clinically‐used therapeutic agents. The preclinical potential of bioorthogonal catalysis has been validated in vitro and in vivo with the in situ generation of a broad range of drugs, including cytotoxic agents, anti‐inflammatory drugs and anxiolytics. In this article, we report our investigations towards the preparation of solid‐supported Cu(I)‐microdevices and their application in bioorthogonal uncaging and click reactions. A range of ligand‐functionalized polymeric devices and off‐on Cu(I)‐sensitive sensors were developed and tested under conditions compatible with life. Last, we present a preliminary exploration of their use for the synthesis of PROTACs through CuAAC assembly of two heterofunctional mating units.