(3S)-3-chloro-5,5-dimethyloxolan-2-one | 1380424-81-6

• 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: (3S)-3-chloro-5,5-dimethyloxolan-2-one
• CAS: 1380424-81-6
• 化学式: C₆H₉ClO₂
• 分子量: 148.589
• InChiKey: XBXLVGOTCPVHFK-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-氯-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43%的产率得到(3S)-3-chloro-5,5-dimethyloxolan-2-one
  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.