trans-(2RS,3SR)-2-allyl-3-hydroxytetrahydropyran | 97102-65-3

• 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: trans-(2RS,3SR)-2-allyl-3-hydroxytetrahydropyran
• 英文别名: (2R*,3S*)-2-allyl-3-hydroxypyran；trans-2-(2-propenyl)tetrahydropyran-3-ol；(2S,3R)-2-prop-2-enyloxan-3-ol
• CAS: 97102-65-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: BTKDCGCMIXPGNH-SFYZADRCSA-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：

  trans-(2RS,3SR)-2-allyl-3-hydroxytetrahydropyran 在 硼烷四氢呋喃络合物 、 hydroxide 、 双氧水 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(2R,3S)-3-(Tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-propan-1-ol
  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
• 作为产物：
  描述：

  2-methoxy-2-allyl-3-hydroxytetrahydropyran 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以80%的产率得到trans-(2RS,3SR)-2-allyl-3-hydroxytetrahydropyran
  参考文献：
  名称：

  环状氧鎓叶立德：多环醚迭代合成的基础

  摘要：

  作为带有多环醚合成的一种可能的方法，使一系列带有远端苄基或烯丙基醚的重氮酮经受各种条件的催化重氮分解和环状氧鎓叶立德的形成。烯丙基醚19，25和29后行有效转化成相应的二（吡喃）和铜（tfacac）存在下的三（吡喃）的产品2，而苄基醚15被转化为二环的产品16和34用的Rh 2（TPA ）4。用Rh 2（tpa）4处理同源底物32提供了具有良好收率的新型中环环丙烷化产物35。

  DOI：

  10.1016/s0040-4020(02)00051-0

文献信息

• Convergent Synthesis of Polycyclic Ethers via the Intramolecular Allylation of α-Acetoxy Ethers and Subsequent Ring-Closing Metathesis
  作者：Isao Kadota、Akio Ohno、Kumiko Matsuda、Yoshinori Yamamoto

  DOI：10.1021/ja025523g

  日期：2002.4.1

  with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

  α-乙酰氧基醚 15-22 的路易斯酸介导反应以良好的收率和高立体选择性得到相应的环化产物 23、25、27、29、31、32、34 和 36。将这些环化产物进行闭环复分解，以良好的收率得到多环醚38-42、44和45。本方法的有用性通过 brevetoxin B (1) 的 CDEF 环系统和甘比尔罗 (2) 的 CDEFG 环系统的收敛合成得到证明。
• A new method for the preparation of the 6,6 and 6,7 ring systems of bicyclic ethers
  作者：Fabienne Simart、Yves Brunel、Sylvie Robin、Gérard Rousseau

  DOI：10.1016/s0040-4020(98)00833-3

  日期：1998.10

  Preparation of 2,7-dioxabicyclo[4.4.0]decane and 2,8-dioxabicyclo[5.4.0]undecane derivatives in five steps from dihydropyran are reported. Transformation of 3-bromo-2-allyloxepane into 2,7-dioxabicyclo-[5.4.0]-undecane is also described.

  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。
• Asymmetric Synthesis of the A-ring Part of Ciguatoxin by the Strategy Based on Diastereoselective Hydroboration and Ring Closing Metathesis
  作者：Kenshu Fujiwara、Hideki Tanaka、Akio Murai

  DOI：10.1246/cl.2000.610

  日期：2000.6

  Asymmetric synthesis of the A-ring part of a marine toxin ciguatoxin (CTX1B) was achieved by the strategy based on ring closing metathesis (RCM), where introduction of the C5 asymmetric center was performed by diastereocontrolled hydroboration of a vinyl ether moiety.

  海洋毒素雪卡毒素（CTX1B）A 环部分的不对称合成是通过基于闭环合成（RCM）的策略实现的，其中 C5 不对称中心的引入是通过乙烯基醚分子的非对映控制氢硼化合实现的。
• 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.
• Convergent Synthesis of Polycyclic Ethers via the Intramolecular Allylation of α-Acetoxy Ethers and Subsequent Ring-Closing Metathesis:  Synthesis of the CDEFG Ring System of Gambierol
  作者：Isao Kadota、Akio Ohno、Kumiko Matsuda、Yoshinori Yamamoto

  DOI：10.1021/ja010911o

  日期：2001.7.1