(S)-5-((R)-3-hydroxy-2-methylpropyl)-5-methylfuran-2(5H)-one | 1357262-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-5-((R)-3-hydroxy-2-methylpropyl)-5-methylfuran-2(5H)-one
• 英文别名: (5S)-5-[(2R)-3-hydroxy-2-methylpropyl]-5-methylfuran-2-one
• CAS: 1357262-42-0
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: BYLUAKFBOZTLHZ-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-((R)-3-hydroxy-2-methylpropyl)-5-methylfuran-2(5H)-one 在 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 丙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， -78.0~100.0 ℃ 、101.33 kPa 条件下， 反应 76.5h， 生成 (8R,10R,E)-methyl 11-(benzyloxy)-8-hydroxy-8,10-dimethylundec-4-enoate
  参考文献：
  名称：

  Mukaiyama–Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17–C28 Fragment of Pectenotoxins

  摘要：

  Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

  DOI：

  10.1021/ol203486p
• 作为产物：
  描述：

  当归内酯 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 (-)-(S)-α,α-diphenylpyrrolidine-2-methanol methyl(diphenyl)silyl ether 、 水 、 三乙胺 、 对硝基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-5-((R)-3-hydroxy-2-methylpropyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Mukaiyama–Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17–C28 Fragment of Pectenotoxins

  摘要：

  Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

  DOI：

  10.1021/ol203486p

文献信息

• Mukaiyama–Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17–C28 Fragment of Pectenotoxins
  作者：Eeva K. Kemppainen、Gokarneswar Sahoo、Arto Valkonen、Petri M. Pihko

  DOI：10.1021/ol203486p

  日期：2012.2.17

  Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.