syn-(+)-(5S,6R)-5-isopropyl-6-vinyl-1,4-dioxan-2-one | 1318230-72-6

• 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: syn-(+)-(5S,6R)-5-isopropyl-6-vinyl-1,4-dioxan-2-one
• CAS: 1318230-72-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ZDASFOQULUYGAT-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (-)-(R)-2-((2-methylhex-5-en-3-yl)oxy)acetic acid 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N'-bis(3,5-di-tert-butylsalicylidine)] chromium(III) chloride 、 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 anti-(-)-(5S,6S)-5-isopropyl-6-vinyl-1,4-dioxan-2-one 、 syn-(+)-(5S,6R)-5-isopropyl-6-vinyl-1,4-dioxan-2-one
  参考文献：
  名称：

  Synthetic Versatility in C–H Oxidation: A Rapid Approach to Differentiated Diols and Pyrans from Simple Olefins

  摘要：

  Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereo-defined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.

  DOI：

  10.1021/ja206013j