d-menthyl 2-chloro-2-fluoro-3-oxo-3-phenylpropanoate | 1306787-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: d-menthyl 2-chloro-2-fluoro-3-oxo-3-phenylpropanoate
• CAS: 1306787-12-1
• 化学式: C₁₉H₂₄ClFO₃
• 分子量: 354.849
• InChiKey: NAVZKGBFUZTBSM-YBKUAAOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  d-menthyl 2-chloro-2-fluoro-3-oxo-3-phenylpropanoate 在 4-二甲氨基吡啶 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(1R,2R)-2-chloro-2-fluoro-3-[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3-oxo-1-phenylpropyl] naphthalene-2-carboxylate
  参考文献：
  名称：

  Enantioselective gem-Chlorofluorination of Active Methylene Compounds Using a Chiral Spiro Oxazoline Ligand

  摘要：

  Highly enantioselective gem-chlorofluorination of active methylene compounds was carried out by using a copper(II) complex of a chiral spiro pyridyl monooxazoline ligand. This reaction yielded alpha-chloro-alpha-fluoro-beta-keto esters and alpha-chloro-alpha-fluoro-beta-keto phosphonates with up to 92% ee. The resulting dihalo beta-keto ester was converted into various alpha-fluoro-alpha-heteroatom-substituted carbonyl compounds via nucleophilic substitution without loss of optical purity. A fully protected beta-amino acid with a gem-chlorofluoromethylene function was also synthesized.

  DOI：

  10.1021/ol201007e
• 作为产物：
  描述：

  d-menthyl 2-chloro-3-oxo-3-phenylpropanoate 在 (R)-Spymox 、 copper(II) bis(trifluoromethanesulfonate) 、 N-氟代双苯磺酰胺 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 d-menthyl 2-chloro-2-fluoro-3-oxo-3-phenylpropanoate
  参考文献：
  名称：

  Enantioselective gem-Chlorofluorination of Active Methylene Compounds Using a Chiral Spiro Oxazoline Ligand

  摘要：

  Highly enantioselective gem-chlorofluorination of active methylene compounds was carried out by using a copper(II) complex of a chiral spiro pyridyl monooxazoline ligand. This reaction yielded alpha-chloro-alpha-fluoro-beta-keto esters and alpha-chloro-alpha-fluoro-beta-keto phosphonates with up to 92% ee. The resulting dihalo beta-keto ester was converted into various alpha-fluoro-alpha-heteroatom-substituted carbonyl compounds via nucleophilic substitution without loss of optical purity. A fully protected beta-amino acid with a gem-chlorofluoromethylene function was also synthesized.

  DOI：

  10.1021/ol201007e

文献信息

• Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution
  作者：Kazutaka Shibatomi、Takuya Okimi、Yoshiyuki Abe、Akira Narayama、Nami Nakamura、Seiji Iwasa

  DOI：10.3762/bjoc.10.30

  日期：——

  of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochemistry of a resulting alpha-chloro-alpha-fluoroaldehyde. Some information about the substrate scope and a possible reaction mechanism are also described which shed more light on the nature of this asymmetric fluorination reaction.

  在先前的研究中表明，外消旋 α-氯醛与手性有机催化剂的对映选择性 α-氟化产生具有高对映选择性的相应 α-氯-α-氟醛。还揭示了起始醛的动力学拆分参与了这种不对称氟化。本文描述了所得 α-氯-α-氟醛的绝对立体化学的测定。还描述了一些关于底物范围和可能的反应机制的信息，这对这种不对称氟化反应的性质有更多的了解。