-4-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-3-methyl-2-butanone | 134265-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: -4-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-3-methyl-2-butanone
• 英文别名: 4-[(3S,6R)-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]-3-methylbutan-2-one
• CAS: 134265-45-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: NIEOTLUVBPGVNR-IVNRZZHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  -4-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-3-methyl-2-butanone 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以72%的产率得到(R)-6-(2-Methyl-3-oxo-butyl)-6H-pyran-3-one
  参考文献：
  名称：

  Lewis acid induced homoallylic C-alkylation. 2. Application to the synthesis of unsaturated diketo C-glycosides. Mechanistic aspect of the reaction

  摘要：

  DOI：

  10.1021/jo00034a051
• 作为产物：
  描述：

  <(Thexyldimethylsilyl)oxy>-3-methyl-3-buten-2-ol 在 sodium methylate 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 -4-(5,6-Dihydro-5-hydroxy-2H-pyran-2-yl)-3-methyl-2-butanone
  参考文献：
  名称：

  Stereocontrolled routes to functionalized [1,8-bc]naphthopyran. A study on the total synthesis of quassinoids and tetrahydronaphthalene antibiotics

  摘要：

  The intramolecular Diels-Alder reactions of (4E,6E)-1-(5,6-dihydro-5-oxo-2H-pyran-2-yl)-2-methyl-4,6-octadienes have been examined with a planned synthesis of quassinoids, chlorotricholides, and mevinic acids. The intramolecular Diels-Alder reactions of 1-(5-oxo-2H-pyran-2-yl)-2-methylocta-4,6-dien-3-ones preferentially afforded products possessing a trans-ring junction. For 1-(2H-pyran-2-yl)-2-methyl-3-[(thexyklimethylsilyl)oxy]-4,6-octadienes the cyclization was controlled by the methyl at C-2 and led to cis-fused or trans-fused derivatives. The reactions were performed under thermal Lewis acid catalyzed and sonochemical conditions with no changes in the reaction selectivity and reaction yields. However, IMDA of 10b in the presence of silica gel produced a dramatic change in the course of the reaction.

  DOI：

  10.1021/jo00067a027

文献信息

• Enantiospecific naphthopyran synthesis by intramolecular diels-alder cyclisation of 4-keto 2,3-unsaturated C-glycosides
  作者：Jean Herscovici、Sylvie Delatre、Kostas Antonakis

  DOI：10.1016/s0040-4039(00)92039-2

  日期：1991.2

  A new intramolecular Diels-Alder cyclization has been studied in connection with problems posed by the synthesis of biologically active molecules possessing a trans naphtopyran or a trans octahydronaphtalene moiety.

  已经研究了一种新的分子内Diels-Alder环化反应，该环化反应是由具有反式萘吡喃或反式八氢萘部分的生物活性分子的合成引起的。