3-(2-Methyl-5-oxooxolan-2-yl)propyl acetate | 1380424-80-5

• 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-(2-Methyl-5-oxooxolan-2-yl)propyl acetate
• 英文别名: 3-(2-methyl-5-oxooxolan-2-yl)propyl acetate
• CAS: 1380424-80-5
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: KOTFFKAZFYDQGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2-methylpent-4-en-1-ol 在 4-二甲氨基吡啶 、 草酰氯 、 palladium 10% on activated carbon 、 C₂₄H₃₂FeN₆⁽²⁺⁾*2F₆Sb^(1-) 、 氢气 、 双氧水 、 二甲基亚砜 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.99h， 生成 3-(2-Methyl-5-oxooxolan-2-yl)propyl 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

• 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.