tetrahydropyranyloxy hex-5-yne-3-ene | 211310-91-7

• 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: tetrahydropyranyloxy hex-5-yne-3-ene
• 英文别名: 2H-Pyran, 2-(5-hexen-3-ynyloxy)tetrahydro-；2-hex-5-en-3-ynoxyoxane
• CAS: 211310-91-7
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: TUEPMAMJETWKGV-UHFFFAOYSA-N

物化性质

• 沸点：
  275.7±35.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydropyranyloxy hex-5-yne-3-ene 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到5-己烯-3-炔-1-醇
  参考文献：
  名称：

  Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua

  摘要：

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00389-5
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 copper(l) iodide 、 四(三苯基膦)钯 、 对甲苯磺酸 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 tetrahydropyranyloxy hex-5-yne-3-ene
  参考文献：
  名称：

  Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua

  摘要：

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00389-5

文献信息

• Novel type of sex pheromone structure identified fromStigmella malella (Stainton) (Lepidoptera: Nepticulidae)
  作者：Miklós Tóth、Gábor Szöcs、Erik J. van Nieukerken、Peter Philipp、Frank Schmidt、Wittko Francke

  DOI：10.1007/bf02033659

  日期：1995.1

  Short-chain unsaturated chiral methyl carbinols are identified as a new class of lepidopteran pheromone components. The natural female-produced pheromone of the banded apple pigmy Stigmella malella (= Nepticula malella) (Stainton) (Lepidoptera: Nepticulidae) was identified to be a mixture of (S)-(E)-6,8-nonadien-2-ol and (S)-(Z)-6,8-nonadien-2-ol. For monitoring traps, a 10:3 E:Z blend at 100-1000 mu g is recommended. It is suggested that pheromones with similar structures may be specific to Nepticulidae and other related microlepidopteran families.
• Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua
  作者：J.S. Yadav、Madabhushi Y. Valli、A.R. Prasad

  DOI：10.1016/s0040-4020(98)00389-5

  日期：1998.6

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.