1-(2-Fluorophenyl)-4-methylpent-3-en-1-ol | 1268248-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-Fluorophenyl)-4-methylpent-3-en-1-ol
• CAS: 1268248-81-2
• 化学式: C₁₂H₁₅FO
• 分子量: 194.249
• InChiKey: WQJJAIPDUAZWKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-Fluorophenyl)-4-methylpent-3-en-1-ol 、 2-氟苯甲醛 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以68%的产率得到
  参考文献：
  名称：

  Prins环化反应区域选择性合成取代四氢呋喃

  摘要：

  功能化四氢呋喃的合成是通过 TfOH 催化的 Prins 环化完成的。在催化量的 TfOH 存在下，反应在内部烯烃碳上区域选择性地进行，得到五元环，而不是典型的六元环。该协议的另一个吸引人的特点是环化过程的无金属催化剂特性。

  DOI：

  10.1055/s-0033-1341273
• 作为产物：
  描述：

  2-氟苯甲醛 、 1-溴-3-甲基-2-丁烯 在 锌 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到1-(2-Fluorophenyl)-4-methylpent-3-en-1-ol
  参考文献：
  名称：

  General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones

  摘要：

  A simple, efficient, and general alpha-prenylation approach for the synthesis of a variety of alpha-prenylated alcohols has been successfully developed. A wide range of alpha-prenylated alcohol derivatives could be obtained in good yields by highly alpha-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 degrees C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct alpha-prenylation of carbonyl compounds in a highly alpha-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.

  DOI：

  10.1021/jo102516a

文献信息

• General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones
  作者：Li-Ming Zhao、Hai-Shan Jin、Li-Jing Wan、Li-Ming Zhang

  DOI：10.1021/jo102516a

  日期：2011.3.18

  A simple, efficient, and general alpha-prenylation approach for the synthesis of a variety of alpha-prenylated alcohols has been successfully developed. A wide range of alpha-prenylated alcohol derivatives could be obtained in good yields by highly alpha-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 degrees C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct alpha-prenylation of carbonyl compounds in a highly alpha-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.
• Regioselective Synthesis of Substituted Tetrahydrofurans through Prins Cyclization
  作者：Li-Ming Zhao、Fei Dou、Rui Sun、Ai-Li Zhang

  DOI：10.1055/s-0033-1341273

  日期：——

  The synthesis of functionalized tetrahydrofurans was ­accomplished through the TfOH-catalyzed Prins cyclization. The reaction proceeded regioselectively at the internal alkene carbon in the presence of catalytic amounts of TfOH to afford the five-membered ring, rather than the typical six-membered ring. Another attractive feature of this protocol is the metal catalyst-free characteristic of the cyclization

  功能化四氢呋喃的合成是通过 TfOH 催化的 Prins 环化完成的。在催化量的 TfOH 存在下，反应在内部烯烃碳上区域选择性地进行，得到五元环，而不是典型的六元环。该协议的另一个吸引人的特点是环化过程的无金属催化剂特性。