(E)-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol | 88730-60-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol
• 英文别名: E-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol；(3E)-6-(2-tetrahydropyranyloxy)-hex-3-en-1-ol；6-tetrahydropyranyloxy-(E)-3-hexen-1-ol；(3E)-6-(Tetrahydro-2H-pyran-2-yloxy)-3-hexen-1-OL；(E)-6-(oxan-2-yloxy)hex-3-en-1-ol
• CAS: 88730-60-3；100048-27-9；21956-80-9
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: GDWHTYMAERZJCX-OWOJBTEDSA-N

物化性质

• 沸点：
  99 °C(Press: 0.035 Torr)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol 在 咪唑 、 六甲基磷酰三胺 、 正丁基锂 、 dilithium tetrachlorocuprate 、 碘 、 triphenylphosphine dibromide 1:1 addition complex 、 三苯基膦 、 calcium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.0h， 生成 (8E,11Z,14Z)-1-(2-tetrahydropyranyloxy)-heptadeca-8,11,14-triene
  参考文献：
  名称：

  Synthesis of (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids and their [1-14C]-radiolabelled analogs

  摘要：

  In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18:3 Delta 9c, 12c, 15t involves a Wittig reaction between 3-(2-tetrahydropyranyloxy)-propylphosphonium salt and (E)-3-hexenal which gave (3Z,6E)-1-(2-tetrahydropyranyloxy)-nonadiene in 66% yield. The transformation of the ether function to a phosphonium salt, followed by a Wittig reaction with 8-(t-butyldimethylsilyloxy)-octanal afforded a C17 trienic ether. A one-carbon homologation of its corresponding bromide with potassium cyanide followed by hydrolysis in basic medium furnished 18:3 Delta 9c, 12c, 15t in high isomeric purity and high radiochemical purity for its [1-C-14]-labelled analog. In the synthesis of 18:3 Delta 9t, 12c, 15c, a Wittig reaction between (E)-6-(2-tetrahydropyranyloxy)-hex-3-enylphosphonium salt, obtained in three steps from 6-(2-tetrahydropyranyloxy)-hex-3-yn-l-ol and (Z)-3-hexenal afforded a C12 (E,Z,Z)-trienic ether. After a six-carbon homologation of this ether, in three steps, the resulting nitrile was hydrolyzed to (9E,12Z, 15Z)-octadecatrienoic acid (99% purity) (99% radiochemical purity of its [1-C-14]-labelled analog).

  DOI：

  10.1016/0009-3084(94)90058-2
• 作为产物：
  描述：

  2-(3-丁炔氧基)四水-2H-吡喃 在 氨 、 sodium 、 lithium 、 ferric nitrate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 (E)-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol
  参考文献：
  名称：

  通过苄基CH活化 将二恶英环和六氢-1 H-苯并[ f ]异色酮立体选择性合成的氧化性小二元和小二元/弗里德-克拉夫特工艺环化†

  摘要：

  （In）和（z）-hex-3-en-1,6-二醇和hept-3-en-1,7-二醇的1-苄醚在In（ OTF）3通过顺序C-H键活化和分子内的环化的Prins，得到相应的反式-和顺-融合六氢-2- ħ -呋喃并[3,2- c ^ ]吡喃和octahydropyrano [4,3- b ]吡喃分别以良好的产率和优异的立体选择性。芳基束缚的高烯丙基苄基醚，例如（E）-和（Z）-6- arylhex -3-烯基醇经过串联普林斯/弗里德尔-克拉夫茨环化反应中的化学计量的量和DDQ的SnCl存在4经由苄基C-H键活化，以提供相应的反式-和顺式-融合六氢1 H-苯并[ f ]异色酮的收率高，具有完全的立体选择性。

  DOI：

  10.1039/c1ob06489d

文献信息

• Syntheses and NMR analyses of the eight geometric isomers of 3,6,8-dodecatrien-1-ol, subterranean termite trail pheromone
  作者：Bryan K. Eya、Otsuka Toshikazu、Kubo Isao、David L. Wood

  DOI：10.1016/s0040-4020(01)88364-2

  日期：1990.1

  via a Wittig olefination reaction. The conver-gent syntheses of 1 consisted of a combination of two fragments, each containing an olefin with a fixed configuration, by formation of a third double bond to give a mixture of two geometric isomers. The mixtures of 1 were resolved by recycle high-performance liquid chromatography methods. 1H and 13C NMR peak assignments of the individual isomers were accomplished

  通过Wittig烯化反应合成了3,6,8-十二碳三烯-1-醇1的八个几何异构体，即地下白蚁的尾随信息素（sp。Banks ）。1的收敛合成由两个片段的组合组成，每个片段包含一个具有固定构型的烯烃，这是通过形成第三个双键给出的两种几何异构体的混合物。1的混合物通过循环高效液相色谱法分离。单个异构体的1 H和13 C NMR峰分配通过同核COSY和一键CH相关光谱法完成。
• Tuning the Reactivity of Oxygen/Sulfur by Acidity of the Catalyst in Prins Cyclization: Oxa- versus Thia-Selectivity
  作者：B. V. Subba Reddy、A. Venkateswarlu、Prashant Borkar、J. S. Yadav、B. Sridhar、René Grée

  DOI：10.1021/jo402832t

  日期：2014.3.21

  An unprecedented oxa- versus thia-selectivity has been observed in Prins cyclization of 6-mercaptohex-3-en-1-ol with aldehydes. In the presence of a stoichiometric amount of strong Lewis or Bronsted acids, the reaction provides the hexahydro-2H-thieno[3,2-c]pyran skeleton predominantly via oxonium-Prins cyclization. In contrast, a catalytic amount of weak Lewis or Bronsted acids provides the hexahydro-2H-thiopyrano[4,3-b]furan preferentially through thionium-Prins cyclization.
• EYA, BRYAN K.;OTSUKA, TOSHIKAZU;KUBO, ISAO;WOOD, DAVID L., TETRAHEDRON, 46,(1990) N, C. 2695-2706
  作者：EYA, BRYAN K.、OTSUKA, TOSHIKAZU、KUBO, ISAO、WOOD, DAVID L.

  DOI：——

  日期：——