(2R,4R)-2-Ethoxy-4-methyl-3,4-dihydro-2H-pyran | 17322-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R)-2-Ethoxy-4-methyl-3,4-dihydro-2H-pyran
• CAS: 17322-76-8
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: FYICJILYYFSSLQ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-ethoxy-4-methyl-3,4-dihydro-2H-pyran 、 (2R,4R)-2-Ethoxy-4-methyl-3,4-dihydro-2H-pyran 、 三异丁基铝 以94%的产率得到
  参考文献：
  名称：

  SNIDER, B. B.;PHILLIPS, G. B., J. ORG. CHEM., 1983, 48, N 17, 2789-2792

  摘要：

  DOI：
• 作为产物：
  描述：

  乙烯基乙醚 、 丁烯-2-醛 在 (tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato))ytterbium(III) 作用下， 以88%的产率得到(2R,4R)-2-Ethoxy-4-methyl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  2-烷氧基-3,4-二氢-2 H-吡喃的氧化重排：立体控制合成4,5-顺式二取代的四氢呋喃酮，包括威士忌和科涅克白兰地内酯和巴巴巴托酸

  摘要：

  用二甲基二环氧乙烷或MTO /脲-H 2 O 2氧化2-烷氧基-3,4-二氢-2 H-吡喃3，然后进行琼斯氧化，导致4,5-顺式-二取代的四氢呋喃酮的重排和立体形成。该方法适用于威士忌内酯9，白兰地内酯10和巴巴果酸17的合成。

  DOI：

  10.1016/j.tet.2009.04.013

文献信息

• Lanthanide catalysis of cycloadditions of heterodienes with enol ethers
  作者：Samuel Danishefsky、Mark Bednarski

  DOI：10.1016/s0040-4039(01)80009-5

  日期：1984.1

  The cycloadditions of enol ethers with α,β-unsaturated aldehydes is catalyzed by Yb(fod)3.

  Yb（fod）3催化烯醇醚与α，β-不饱和醛的环加成反应。
• Lanthanide catalysts for the hetero Diels–Alder reaction: effect of ligand structure and acidity
  作者：Claude Spino、Laurel L. Clouston、David J. Berg

  DOI：10.1139/v97-125

  日期：1997.8.1

  A series of yttrium, ytterbium, and lanthanum hexa-or heptacoordinate complexes were prepared and their catalytic activities tested in the hetero Diels–Alder reaction between crotonaldehyde and ethyl vinyl ether. It was found that a pK_a below 7 of the ligand was necessary but not sufficient for catalytic activity. It was determined that the ligand should possess a perfluoromethyl-β-diketonate functionality. Other factors such as bite angle and hinging motion may also play a determining role. Keywords: lanthanide, catalyst, hetero Dielsis–Alder, yttrium, ytterbium, lanthanum.

  一系列的钇、镱和镧的六或七配位配合物已被制备并在丁烯醛和乙基乙烯醚的杂Diels-Alder反应中测试了它们的催化活性。发现配体的pK_a低于7是必要的但不足以保证催化活性。确定了配体应具有全氟甲基-β-二酮酸酯功能。其他因素，如咬合角度和铰链运动，也可能发挥决定性作用。关键词：镧系元素、催化剂、杂Diels-Alder、钇、镱、镧。
• Novel, air-stable, lanthanide catalysts for the hetero Diels–Alder reaction
  作者：Claude Spino、Laurel Clouston、David Berg

  DOI：10.1139/v96-195

  日期：1996.9.1

  Novel, air-stable, yttrium and ytterbium complexes were found effective in the catalysis of the typical hetero Diels–Alder reaction of crotonaldehyde and ethylvinyl ether. They represent an attractive solution to the problem of ligand lability in the realm of lanthanide catalysts. Key words: lanthanide, catalyst, hetero Diels–Alder, yttrium, ytterbium.

  发现稳定空气的新型钇和镱络合物在催化克罗托醛和乙基乙烯醚的典型杂环Diels-Alder反应中具有很高的效率。它们是在镧系催化剂领域中解决配体不稳定性问题的一个有吸引力的解决方案。关键词：镧系、催化剂、杂环Diels-Alder、钇、镱。
• Highly Enantioselective Inverse-Electron-Demand Hetero-Diels–Alder Reactions of α,β-Unsaturated Aldehydes This work was supported by the NIH (GM-59316), with additional support from the Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung (postdoctoral fellowship to K.G.), and the National Science Foundation (predoctoral fellowship to D.E.C.). We are grateful to Dr. R. Staples for carrying out the X-ray crystal structure analysis of 1.
  作者：Karl Gademann、David E. Chavez、Eric N. Jacobsen

  DOI：10.1002/1521-3773(20020816)41:16<3059::aid-anie3059>3.0.co;2-i

  日期：2002.8.16
• Oxidative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans: stereocontrolled synthesis of 4,5-cis-disubstituted tetrahydrofuranones including whisky and cognac lactones and crobarbatic acid
  作者：Alan Armstrong、Cassim Ashraff、Hunsuk Chung、Lorraine Murtagh

  DOI：10.1016/j.tet.2009.04.013

  日期：2009.6

  Oxidation of 2-alkoxy-3,4-dihydro-2H-pyrans 3 with dimethyldioxirane or MTO/urea–H2O2 followed by Jones oxidation leads to rearrangement and stereocontrolled formation of 4,5-cis-disubstituted tetrahydrofuranones. The method is applied to the synthesis of the whisky lactone 9, cognac lactone 10 and crobarbatic acid 17.

  用二甲基二环氧乙烷或MTO /脲-H 2 O 2氧化2-烷氧基-3,4-二氢-2 H-吡喃3，然后进行琼斯氧化，导致4,5-顺式-二取代的四氢呋喃酮的重排和立体形成。该方法适用于威士忌内酯9，白兰地内酯10和巴巴果酸17的合成。