4-(4-hydroxymethyl-furan-2-yl)-butan-1-ol | 1309387-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4-(4-hydroxymethyl-furan-2-yl)-butan-1-ol
• 英文别名: 4-[4-(Hydroxymethyl)furan-2-yl]butan-1-ol；4-[4-(hydroxymethyl)furan-2-yl]butan-1-ol
• CAS: 1309387-79-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: STZMARDTAXETMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-8-(tetrahydro-pyran-2-yloxy)-oct-3-yn-2-ol 在 乙醚 、 四丁基氟化铵 、 mercuric triflate 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 4.08h， 生成 4-(4-hydroxymethyl-furan-2-yl)-butan-1-ol
  参考文献：
  名称：

  A Highly Efficient Access to Spiroketals, Mono-unsaturated Spiroketals, and Furans: Hg(II)-Catalyzed Cyclization of Alkyne Diols and Triols

  摘要：

  Hg(II) salts are identified as highly efficient catalysts for the versatile construction of spiroketals from alkyne diols in aqueous conditions. Monounsaturated spiroketals and furans were accessed with equal ease when propargylic triols (or propargylic diols) were subjected to similar conditions. Even the semiprotected alkyne diols gave the corresponding spiroketals with the same ease in a cascade manner. The reactions are Instant and high yielding at ambient temperatures. Regioselectivity issues are well addressed.

  DOI：

  10.1021/ol201102x

文献信息

• Au(I)-Catalyzed Cyclization of Epoxyalkynes to Allylic Alcohol Containing Spiroketals and Application to the Total Synthesis of (−)-Alotaketal A
  作者：Jaeyeon Lee、Jiheon Kim、Hee-Yoon Lee

  DOI：10.1021/acs.orglett.0c01130

  日期：2020.6.5

  spiroketalization of epoxyalkynes accompanied by epoxide rearrangement into the corresponding allylic alcohol was developed for the construction of functionalized spiroketals. This new synthetic methodology for unsaturated spiroketals warranted a facile total synthesis of alotaketal A from carvone via a corresponding epoxyalkyne precursor.

  开发了金催化的环氧炔烃串联螺环缩合并伴随环氧化物重排成相应的烯丙醇，用于功能化螺缩环的构建。这种用于不饱和螺环酮化合物的新的合成方法确保了通过相应的环氧炔烃前体从香芹酮中轻松合成总焦油A。
• A Highly Efficient Access to Spiroketals, Mono-unsaturated Spiroketals, and Furans: Hg(II)-Catalyzed Cyclization of Alkyne Diols and Triols
  作者：Kontham Ravindar、Maddi Sridhar Reddy、Pierre Deslongchamps

  DOI：10.1021/ol201102x

  日期：2011.6.17

  Hg(II) salts are identified as highly efficient catalysts for the versatile construction of spiroketals from alkyne diols in aqueous conditions. Monounsaturated spiroketals and furans were accessed with equal ease when propargylic triols (or propargylic diols) were subjected to similar conditions. Even the semiprotected alkyne diols gave the corresponding spiroketals with the same ease in a cascade manner. The reactions are Instant and high yielding at ambient temperatures. Regioselectivity issues are well addressed.