(2-methyl-5-oxotetrahydrofuran-2-yl)methyl acetate | 1380424-79-2

• 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: (2-methyl-5-oxotetrahydrofuran-2-yl)methyl acetate
• 英文别名: (+/-)-5-methyl-5-(1-acetoxymethyl)dihydrofuran-2-one；(2-Methyl-5-oxooxolan-2-yl)methyl acetate；(2-methyl-5-oxooxolan-2-yl)methyl acetate
• CAS: 1380424-79-2
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: UCYZHYPKTBAOKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-乙酰氧基-4-甲基戊酸 在 C₂₄H₃₂FeN₆⁽²⁺⁾*2F₆Sb^(1-) 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 0.35h， 以27%的产率得到(2-methyl-5-oxotetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

  摘要：

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

  DOI：

  10.1021/ja301685r

文献信息

• Low‐Impact Synthesis of γ‐Lactones Through Photoinduced Baeyer‐Villiger Oxidation of Cyclic Ketones
  作者：Maria Chiara Cabua、Viktoria Velichko、Luca Pilia、Davide Moi、Francesco Secci

  DOI：10.1002/ejoc.202400226

  日期：——

  A photocatalyzed oxidation of functionalized cyclobutanones to access γ-lactones has been performed in acetonitrile at room temperature, using 9,10-anthraquinone as catalysts in the presence of TFA. The process furnish good to excellent yields of the desired compounds in 4–16 h reaction and after simple filtration of the recyclable catalyst.

  在室温下，使用 9,10-蒽醌作为催化剂，在 TFA 存在下，在乙腈中进行了官能化环丁酮的光催化氧化以获得 γ-内酯。该工艺在 4-16 小时的反应中以及在对可回收催化剂进行简单过滤后，可提供良好至优异的所需化合物收率。
• Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias
  作者：Marinus A. Bigi、Sean A. Reed、M. Christina White

  DOI：10.1021/ja301685r

  日期：2012.6.13

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.