(R)-5-((R)-3-(benzyloxy)-2-methylpropyl)-5-methyldihydrofuran-2(3H)-one | 1357262-43-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-5-((R)-3-(benzyloxy)-2-methylpropyl)-5-methyldihydrofuran-2(3H)-one
• 英文别名: (5R)-5-methyl-5-[(2R)-2-methyl-3-phenylmethoxypropyl]oxolan-2-one
• CAS: 1357262-43-1
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: WJCFLQUJDRPUNM-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-((R)-3-(benzyloxy)-2-methylpropyl)-5-methyldihydrofuran-2(3H)-one 在 二异丁基氢化铝 、 丙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 74.0h， 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 、 (2S,5S)-2,5-二苯基吡咯烷 、 cerium(III) chloride heptahydrate 、 5%-palladium/activated carbon 、 水 、 氢气 、 sodium hydride 、 三乙胺 、 对硝基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 29.5h， 生成 (R)-5-((R)-3-(benzyloxy)-2-methylpropyl)-5-methyldihydrofuran-2(3H)-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.