4-辛烯-1-醇 | 67700-26-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-辛烯-1-醇
• 英文名称: oct-4-en-1-ol
• 英文别名: 4-Octen-1-ol
• CAS: 67700-26-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: OZQBPZSICOOLGU-UHFFFAOYSA-N

物化性质

• 熔点：
  -31.5°C (estimate)
• 沸点：
  196℃
• 密度：
  0.845
• 闪点：
  77℃
• 物理描述：
  Clear, colourless liquid; Powerful, sweet, earthy odour with a strong herbaceous note
• 溶解度：
  Insoluble in water; soluble in non-polar organic solvents
• 折光率：
  1.444-1.450

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-辛烯-1-醇 在 三乙胺 、 lithium bromide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 3.0h， 生成 1-bromooct-4-ene
  参考文献：
  名称：

  摘要：

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).

  DOI：

  10.1023/a:1026047515568
• 作为产物：
  描述：

  2-vinyltetrahydrofuran 、 乙基溴化镁 在 titanium(IV) isopropylate 作用下， 以 乙醚 为溶剂， 以55%的产率得到4-辛烯-1-醇
  参考文献：
  名称：

  摘要：

  Reaction of 2-vinyltetrahydrofuran and 2-vinyltetrahydropyran with ethylmagnesium bromude in the presence ot titanium(IV) isopropoxide afforded in moderate selectivity trans-4-octen-1-ol and trans-5-nonen-1-ol respectively. Best yields and high stereochemical purity of products were obtained in ethylation under these conditions of 2-(cis-1-propenyl)tetrahydrofuran, 2-(cis-1-proprnyl)- and 2- (trans-1-propenyl) tetrahydropyran. It is assumed that the key organometallic intermediate formed was diisopropoxy-titanacycloprpopane, and direction of its addition to the doubel bond governed the streochemistry of the resulting product. The obtained trans-4-octen-1-ol and trans-7-methyl-5-nonen-1-ol were applied as initial products in the synthesis of sex pheromones of lesser plum worm (Grafolita funebrana) and tea leaf roller moth (Adoxophyes sp).

  DOI：

  10.1023/a:1026047515568

文献信息

• An <i>Endo</i> ‐Selective Epoxide‐Opening Cascade for the Fast Assembly of the Polycyclic Core Structure of Marine Ladder Polyethers
  作者：Feng‐Xing Li、Shu‐Jian Ren、Pei‐Fang Li、Peng Yang、Jin Qu

  DOI：10.1002/anie.202007980

  日期：2020.10.12

  cyclization reactions of trisubstituted epoxy alcohols. Starting from readily accessible homochiral polyepoxy alcohols with a methyl group at all the endo‐cyclization sites, we were able to construct polyethers up to five consecutive fused 6‐, 7‐, and/or 8‐membered rings in one step. Notably, molecules with the 7/7/6/6 and 7/7/6/7/6 polyether frameworks of hemibrevetoxin B and brevenal, respectively

  由聚环氧化物前体快速合成海洋阶梯聚醚的方法（类似于中西所假设的生物合成途径）受到以下事实的阻碍，即外选择性环氧化物开放环化级联反应可产生THF型聚醚，而不是内选择性级联反应提供所需的产品。我们发现，全氟叔丁醇（PFTB）与1-乙基-3-甲基咪唑鎓四氟硼酸酯（[EMIM] BF 4）配合使用可促进三取代环氧醇的内选择性环氧化物开环反应。从在所有的用甲基容易获得的纯手性环氧醇开始内在环化位点，我们能够一步一步构建多达五个连续的6、7和/或8元稠环的聚醚。值得注意的是，可以分别以40％和17％的化学产率合成具有半短毒素B和brevenal的7/7/6/6和7/7/6/7/6聚醚骨架的分子。