(R)-5-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one | 1449123-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one
• 英文别名: (5R)-5-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 1449123-29-8
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: ITUDHKPFAMAKSJ-MRVWCRGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one 在 盐酸 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.67h， 生成 (-)-(3aS,5R,6S,6aS)-6-hydroxy-5-phenyltetrahydrofuro[3,2-b]furan-2(5H)-one
  参考文献：
  名称：

  A C–H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs

  摘要：

  Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C H activation/resolution is evaluated against the state-of-the-art. The C H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.012
• 作为产物：
  描述：

  (E)-5-styryltetrahydrofuran-2(3H)-one 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium ferricyanide 、 水 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (R)-5-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A C–H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs

  摘要：

  Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C H activation/resolution is evaluated against the state-of-the-art. The C H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.012

文献信息

• A C–H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs
  作者：Dustin J. Covell、M. Christina White

  DOI：10.1016/j.tet.2013.05.012

  日期：2013.9

  Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C H activation/resolution is evaluated against the state-of-the-art. The C H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility. (C) 2013 Elsevier Ltd. All rights reserved.