2-allyl-3-hydroxytetrahydropyran | 97102-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-allyl-3-hydroxytetrahydropyran
• 英文别名: cis-2-(2-propenyl)tetrahydropyran-3-ol；(2S,3S)-2-prop-2-enyloxan-3-ol
• CAS: 97102-64-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: BTKDCGCMIXPGNH-YUMQZZPRSA-N

物化性质

• 沸点：
  226.5±23.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-allyl-3-hydroxytetrahydropyran 在 臭氧 、 三苯基膦 作用下， 生成 (1R*,6R*)-8-hydroxy2,7-dioxabicyclo[4.3.0]nonane
  参考文献：
  名称：

  一种制备双环醚的6,6和6,7环系统的新方法

  摘要：

  据报道，由二氢吡喃分五步制备2，7-二氧杂双环[4.4.0]癸烷和2，8-二氧杂双环[5.4.0]十一烷衍生物。还描述了3-溴-2-烯丙基环庚烷向2，7-二氧杂双环-[5.4.0]-十一烷的转化。

  DOI：

  10.1016/s0040-4020(98)00833-3
• 作为产物：
  描述：

  tetrahydro-2H-pyran-2,3-diol 在 吡啶 、 sodium hydroxide 、 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 生成 2-allyl-3-hydroxytetrahydropyran
  参考文献：
  名称：

  Methods for pyranoannulation: an approach to a new class of polyethers

  摘要：

  Several methods have been developed for fusing a pyran ring to an existing pyran ring structure such that the ring oxygens assume a vicinal (ethylene glycol) relationship. The tricyclic structure 13, a previously unknown substance, was prepared through a combination of these methods.

  DOI：

  10.1021/jo00216a049

文献信息

• NHC-Catalyzed Ring Expansion of Oxacycloalkane-2-carboxaldehydes: A Versatile Synthesis of Lactones
  作者：Li Wang、Karen Thai、Michel Gravel

  DOI：10.1021/ol8029005

  日期：2009.2.19

  Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.

  咪唑啉鎓衍生的卡宾催化氧杂环烷-2-甲醛的扩环内酯化反应。在温和的反应条件下，可以有效地形成各种功能化的五元，六元和七元内酯。卡宾催化剂的电子性质极大地影响了这种构建内酯的新方法的成功。
• Allylation using allyborates
  作者：Roger Hunter、Joseph P. Michael、Geoffrey D. Tomlinson

  DOI：10.1016/s0040-4020(01)80802-4

  日期：1994.1

  A study has been carried out on the scope of allylation of a range of acetals activated by trimethylsilyl trfluoromethanesulfonate (TMSOTf) using a humber of organoborates. Intermolecular allylation of acyclic acetals proceeds smoothly and in high yield using lithium n-butyltriallylborate or lithium methyltriallylborate in THF at -78 degrees C while 1,3-dioxanes and dioxolanes give rise to some reduction products. Intramolecular allylation may be carried out via anchoring the triallylborane using an alkoxide anion. Mechanistic studies indicate that allyl transfer is from boron and not silicon, while stereoselectivity studies on the crotylation of acyclic acetals as well as the allylation of chiral acetals derived from (2R,4R)-pentanediol indicate moderate levels of diastereoselection.