2-but-1-enyltetrahydrofuran | 13179-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 2-but-1-enyltetrahydrofuran
• 英文别名: 2-but-1-enyl-tetrahydro-furan；2-(But-1-enyl)-tetrahydrofuran (cis,trans)；2-But-1-enyloxolane；2-but-1-enyloxolane
• CAS: 13179-79-8
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: AMMRVUSPENXFRB-UHFFFAOYSA-N

物化性质

• 熔点：
  80-84 °C
• 沸点：
  157.3±19.0 °C(predicted)
• 密度：
  0.954±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-but-1-enyltetrahydrofuran 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(4E,6E)-octa-4,6-dien-1-ol
  参考文献：
  名称：

  Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

  摘要：

  Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00918-1
• 作为产物：
  描述：

  四氢呋喃-2-甲醛 、 propylidenetriphenylphosphorane 以 四氢呋喃 为溶剂， 生成 2-but-1-enyltetrahydrofuran
  参考文献：
  名称：

  Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

  摘要：

  Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00918-1

文献信息

• Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant
  作者：Fulvio Cominetti、Annamaria Deagostino、Cristina Prandi、Paolo Venturello

  DOI：10.1016/s0040-4020(98)00918-1

  日期：1998.11

  Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TPAP and NMO. Subsequent Wittig reaction afforded 2-alk-1-enyltetrahydrofurans (2 and 3) that on be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E, 6E)-nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit ny, Anastrepha suspensa. (C) 1998 Elsevier Science Ltd. All rights reserved.