2-Hydroxymethyl-4,5-dimethyl-tetrahydrofuran | 16014-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-Hydroxymethyl-4,5-dimethyl-tetrahydrofuran
• 英文别名: (4,5-Dimethyloxolan-2-yl)methanol
• CAS: 16014-98-5
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: CIQGJQPXAWEHIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Ethoxypent-4-en-1-ol 在 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 2-Hydroxymethyl-4,5-dimethyl-tetrahydrofuran 、 4-甲氧基丁-1-炔 、 [(2S,4S,5S)-4,5-dimethyloxolan-2-yl]methanol
  参考文献：
  名称：

  Strategies to Control Alkoxy Radical-Initiated Relay Cyclizations for the Synthesis of Oxygenated Tetrahydrofuran Motifs

  摘要：

  Radical relay cyclizations initiated by alkoxy radicals are a powerful tool for the rapid construction of substituted tetrahydrofurans. The scope of these relay cyclizations has been dramatically increased with the development of two strategies that utilize an oxygen atom in the substrate to accelerate the desired hydrogen atom transfer (HAT) over competing pathways. This has enabled a chemoselective 1,6-HAT over a competing 1,5-HAT. Furthermore, this allows for a chemoselective 1,5-HAT over competing direct cyclizations and beta-fragmentations. Oxygen atom incorporation leads to a general increase in cyclization diastereoselectivity over carbon analogues. This chemoselective relay cyclization strategy was utilized in the improved synthesis of the tetrahydrofuran fragment in (-)-amphidinolide K.

  DOI：

  10.1021/jo502499a

文献信息

• Catalyst and process for hydrogenating olefinically unsaturated compound
  申请人：JSR Corporation

  公开号：EP0974602B1

  公开（公告）日：2004-01-02
• US6291596B1
  申请人：——

  公开号：US6291596B1

  公开（公告）日：2001-09-18
• [EN] COMPOSITIONS AND METHODS FOR TREATING LEUKEMIA<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE LA LEUCÉMIE
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2011143660A2

  公开（公告）日：2011-11-17

  The invention provides compositions, methods, and kits for the treatment of acute myeloid leukemia in a subject.
• Strategies to Control Alkoxy Radical-Initiated Relay Cyclizations for the Synthesis of Oxygenated Tetrahydrofuran Motifs
  作者：Hai Zhu、Joe C. T. Leung、Glenn M. Sammis

  DOI：10.1021/jo502499a

  日期：2015.1.16

  Radical relay cyclizations initiated by alkoxy radicals are a powerful tool for the rapid construction of substituted tetrahydrofurans. The scope of these relay cyclizations has been dramatically increased with the development of two strategies that utilize an oxygen atom in the substrate to accelerate the desired hydrogen atom transfer (HAT) over competing pathways. This has enabled a chemoselective 1,6-HAT over a competing 1,5-HAT. Furthermore, this allows for a chemoselective 1,5-HAT over competing direct cyclizations and beta-fragmentations. Oxygen atom incorporation leads to a general increase in cyclization diastereoselectivity over carbon analogues. This chemoselective relay cyclization strategy was utilized in the improved synthesis of the tetrahydrofuran fragment in (-)-amphidinolide K.