(+)-2-(((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-yl)oxy)acetic acid | 1318231-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-2-(((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-yl)oxy)acetic acid
• 英文别名: 2-[(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-enoxy]acetic acid
• CAS: 1318231-24-1
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: SFLARHOLODCEMC-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-2-(((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-yl)oxy)acetic acid 在 三甲基氯硅烷 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N'-bis(3,5-di-tert-butylsalicylidine)] chromium(III) chloride 、 potassium carbonate 、 三乙胺 、 对苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 methyl (+)-(2R,6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3,6-dihydro-2H-pyran-2-carboxylate
  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
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 sodium hydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (+)-2-(((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-yl)oxy)acetic acid
  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