(2S)-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolan)-3(6H)-one | 99648-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolan)-3(6H)-one
• CAS: 99648-52-9
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: LLEOWGYORBGOTE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.62
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolan)-3(6H)-one 在 amberlite 120 (H+ form) 作用下， 以 水 为溶剂， 反应 1.0h， 以93%的产率得到2-呋喃基羟基甲基甲酮
  参考文献：
  名称：

  d-Fructose- and l-sorbose-derived endo- and exo-hydroxyglycal esters and some of their chemistry

  摘要：

  Dehydrobrominations of benzoylated beta-D-fructopyranosyl and alpha-L-sorbo-pyranosyl bromides have been examined to obtain suitable conditions for effecting the elimination toward the exo- as well as the endo-positions. In the fructose case, exposure to DBU in acetonitrile generates the exo-hydroxyfructal ester (81%) while refluxing in xylene gives the endo analog (53%). In the L-sorbose case, the regioselectivities are the inverse. Simple reactions of exo- and endo-products provide a series of highly versatile enantiopure six-carbon building blocks, together with a crystalline derivative of the fungal metabolite microthecin. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.018
• 作为产物：
  描述：

  1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 在 咪唑 、 molecular sieve 、 氢气 、 碘 、 potassium hydride 、 镍 、 溶剂黄146 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 (2S)-2',2'-dimethyl-2H-pyran-2-spiro-4'-(1',3'-dioxolan)-3(6H)-one
  参考文献：
  名称：

  Structural Probing of Ketone Catalysts for Asymmetric Epoxidation

  摘要：

  A series of chiral ketones derived from carbohydrates were investigated as catalysts for the asymmetric epoxidation. Fructose-derived ketones are found to be efficient catalysts. The studies show that the structural requirements for the ketone catalysts are very stringent and different types of olefins may require ketones with different structural arrangements. The current study allows us to further understand the chiral ketone catalyzed asymmetric epoxidation and provides some insight for the development of new catalysts.

  DOI：

  10.1021/jo9817218

文献信息

• Lichtenthaler, Frieder W.; Doleschal, Walter; Hahn, Susanne, Liebigs Annalen der Chemie, 1985, # 12, p. 2454 - 2464
  作者：Lichtenthaler, Frieder W.、Doleschal, Walter、Hahn, Susanne

  DOI：——

  日期：——