1-(5,6-dihydro-4H-pyran-2-yl)-2-isopropyl-propenone | 649570-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5,6-dihydro-4H-pyran-2-yl)-2-isopropyl-propenone
• 英文别名: 1-(3,4-dihydro-2H-pyran-6-yl)-3-methyl-2-methylenebutan-1-one；1-(3,4-Dihydro-2H-pyran-6-yl)-3-methyl-2-methylidenebutan-1-one；1-(3,4-dihydro-2H-pyran-6-yl)-3-methyl-2-methylidenebutan-1-one
• CAS: 649570-48-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: PJXSBIMEEIHXOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5,6-dihydro-4H-pyran-2-yl)-2-isopropyl-propenone 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 以93%的产率得到6-isopropyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one
  参考文献：
  名称：

  Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones

  摘要：

  [GRAPHICS]Expeditious and high-yielding Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones are described. An example of a catalytic asymmetric Nazarov cyclization is presented.

  DOI：

  10.1021/ol036019z
• 作为产物：
  描述：

  3-甲基-2-亚甲基丁醛 在 吡啶 、 叔丁基锂 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 生成 1-(5,6-dihydro-4H-pyran-2-yl)-2-isopropyl-propenone
  参考文献：
  名称：

  Efficient Nazarov Cyclizations of 2-Alkoxy-1,4-pentadien-3-ones

  摘要：

  [GRAPHICS]Expeditious and high-yielding Nazarov cyclizations of 2-alkoxy-1,4-pentadien-3-ones are described. An example of a catalytic asymmetric Nazarov cyclization is presented.

  DOI：

  10.1021/ol036019z

文献信息

• Nazarov-type Reactions in Water
  作者：Masaya Kokubo、Shū Kobayashi

  DOI：10.1002/asia.200800461

  日期：2009.4.6

  AbstractDifferent in water! We have developed Nazarov‐type reactions in water. Different reaction courses compared with those in organic solvents are observed in water. In the presence of a scandium based, surfactant‐type catalyst, water‐trapping products are obtained exclusively. The results presented are unprecedented and provide a valuable extension to information available regarding organic reactions in water.magnified image
• 4-Toluenesulfonic acid: an environmentally benign catalyst for Nazarov cyclizations
  作者：Mukkanti Amere、Jérôme Blanchet、Marie-Claire Lasne、Jacques Rouden

  DOI：10.1016/j.tetlet.2008.02.091

  日期：2008.4

  An efficient metal-free catalytic protocol for the electrocyclization of alpha-alkoxydienones to cyclopentenones (Nazarov reaction) in near to quantitative yields is described. The key parameters are the use of inexpensive 4-toluenesulfonic acid in 5 mol % at room temperature in acetonitrile or under solvent-free conditions. The versatility of the transformation is demonstrated with unpolarized dienones with good regioselectivities and excellent yields. (c) 2008 Elsevier Ltd. All rights reserved.