3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one
• 英文别名: 2-acetyl-2-propargyl-γ-butyrolactone；2(3H)-Furanone, 3-acetyldihydro-3-(2-propynyl)-；3-acetyl-3-prop-2-ynyloxolan-2-one
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: GLTBYRHJUJWEHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (+/-)-anti-2-propargyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone 、 (+/-)-syn-2-propargyl-2-[1'-(1'-hydroxyethyl)]-γ-butyrolactone
  参考文献：
  名称：

  STUDIES ON THE DIASTEREO- SELECTIVE REDUCTION OF 2-ACETYL-2-ALKYL- γ-BUTYROLACTONES WITH BORON HYDRIDES*

  摘要：

  Reduction of 2-acetyl-2-alkyl-gamma-butyrolactone derivatives with boron hydrides in the presence and absence of several chelating agents were studied. This process is influenced more by steric than chelation factors, yielding the isomeric alcohols syn (13-23) and anti (14-24) in good diastereomeric excess.

  DOI：

  10.1081/scc-120002396
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 、 3-溴丙炔 在 potassium tert-butylate 、 1,2,3,4,5-pentamethyl-1H-imidazol-3-ium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到3-acetyl-3-(prop-2-ynyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  N-杂环烯烃作为碱促进烷基化反应的高效相转移催化剂

  摘要：

  N-杂环烯烃（NHOs）由于其强大的Bronsted / Lewis基础性，最近已成为多种化学反应的有效促进剂。在这里，我们将NHO的新颖应用报告为高效...

  DOI：

  10.1039/c6cc03771b

文献信息

• N-Heterocyclic olefins as efficient phase-transfer catalysts for base-promoted alkylation reactions
  作者：Marcus Blümel、Reece D. Crocker、Jason B. Harper、Dieter Enders、Thanh V. Nguyen

  DOI：10.1039/c6cc03771b

  日期：——

  N-Heterocyclic Olefins (NHOs) have very recently emerged as efficient promoters for several chemical reactions due to their strong Bronsted/Lewis basicities. Here we report the novel application of NHOs as efficient...

  N-杂环烯烃（NHOs）由于其强大的Bronsted / Lewis基础性，最近已成为多种化学反应的有效促进剂。在这里，我们将NHO的新颖应用报告为高效...
• STUDIES ON THE DIASTEREO- SELECTIVE REDUCTION OF 2-ACETYL-2-ALKYL- γ-BUTYROLACTONES WITH BORON HYDRIDES*
  作者：Lis H. P. Teixeira、Maria Cecília B. V. de Souza、Maria da Conceição K. V. Ramos、Francisco R. de Aquino Neto、Eliezer J. Barreiro、Carlos A. M. Fraga

  DOI：10.1081/scc-120002396

  日期：2002.1.1

  Reduction of 2-acetyl-2-alkyl-gamma-butyrolactone derivatives with boron hydrides in the presence and absence of several chelating agents were studied. This process is influenced more by steric than chelation factors, yielding the isomeric alcohols syn (13-23) and anti (14-24) in good diastereomeric excess.