(E)-hepta-1,5-dien-3-ol | 79705-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-hepta-1,5-dien-3-ol
• 英文别名: (5E)-1,5-heptadien-3-ol；(5E)-hepta-1,5-dien-3-ol
• CAS: 79705-01-4
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: CPGDYOFWPOGTGF-HWKANZROSA-N

物化性质

• 沸点：
  163.5±9.0 °C(Predicted)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (E)-hepta-1,5-dien-3-ol 在 mercury(II) diacetate 作用下， 以 四氢呋喃 为溶剂， 生成 trans,trans-nona-4,7-dienal
  参考文献：
  名称：

  SEQUENTIAL [2,3]WITTIG AND CLAISEN REARRANGEMENT: A FACILE SYNTHETIC METHOD FOR (E,E)-4,7-ALKADIENALS AND -ALKADIENOIC ACIDS. A NEW FORMAL SYNTHESIS OF (±)-CERULENIN

  摘要：

  双烯丙基醚的亲区选择性[2,3]Wittig重排，以及随后的Claisen重排，可以方便地得到（E,E）-4,7-烯丙二烯醛和烯丙二烯酸。在具有多种生物活性的（±）-青霉烯素的新形式合成中，展示了西格马拓扑序列的多功能性。

  DOI：

  10.1246/cl.1981.1721
• 作为产物：
  描述：

  3-戊烯酸 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-hepta-1,5-dien-3-ol
  参考文献：
  名称：

  Influence of the Chemical Structure on Odor Qualities and Odor Thresholds in Homologous Series of Alka-1,5-dien-3-ones, Alk-1-en-3-ones, Alka-1,5-dien-3-ols, and Alk-1-en-3-ols

  摘要：

  Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.

  DOI：

  10.1021/jf404885j

文献信息

• New sigmatropic sequences based on the [2,3]-wittig rearrangement of the bis-allylic ether system
  作者：Kōichi Mikami、Naoyuki Kishi、Takeshi Nakai、Yoshiji Fujita

  DOI：10.1016/s0040-4020(01)90580-0

  日期：1986.1

  Four new sigmatropic sequences triggered by the regiocontrolled [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers (1) to the l,5-dien-3-ols (2) arc described, which provide unique, regiocontrolled methods for the synthesis of a wide variety of unsaturated carbonyl compounds possessing interesting molecular frameworks. The newly developed sequences include the [2,3]-Wittig-Claisen, the

  描述了由不对称双烯丙基醚（1）到1,5-二烯-3-醇（2）的区域控制[2,3] -Wittig重排触发的四个新的sigmatropic序列，它们提供了独特的区域控制方法具有令人感兴趣的分子框架的各种不饱和羰基化合物的合成。新开发的序列包括[2,3] -Wittig-Claisen，串联[2,3] -Wittig-oxy-Cope，串联oxy-Cope-Claisen和串联oxy-Cope-Cope序列。
• Relevance of oxyanion stereochemistry to chirality transfer in anionic oxy-Cope rearrangements
  作者：Leo A. Paquette、George D. Maynard

  DOI：10.1021/ja00039a011

  日期：1992.6

  undergo anionic oxy-Cope rearrangement under the exclusice control of oxyanion orientation with a 58-64% preference for equatorial oxygen. Six semicyclic dienols have also been synthesized where the preferred oxyanion-driven sigmatropic rearrangement pathway is obligatorily pitted against π-facial biases offered by 4-tert-butylcyclohexenyl, norbornenyl, and camphenyl rings. These rearrangements therefore

  几何和光学纯 (3R,5E)- 和 (3R,5Z)-1,5-heptadien-3-ols 在氧阴离子取向的排他控制下经历阴离子氧-Cope 重排，对赤道氧的偏好为 58-64%。还合成了六种半环二烯醇，其中优选的氧阴离子驱动的 sigmatropic 重排途径必须与 4-叔丁基环己烯基、降冰片烯基和凸轮苯基环提供的 π 面偏差相抗衡。因此，这些重排为控制手性转移水平和方向的那些因素提供了特别严格的测试。数据显示氧阴离子不喜欢参与 1,3-二轴关系
• Paquette, Leo A.; Maynard, George D., Angewandte Chemie, 1991, vol. 103, # 10, p. 1392 - 1394
  作者：Paquette, Leo A.、Maynard, George D.

  DOI：——

  日期：——
• [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers. Facile method for regio- and stereoselective synthesis of 1,5-dien-3-ols
  作者：T. Nakai、K. Mikami、S. Taya、Y. Fujita

  DOI：10.1021/ja00411a038

  日期：1981.10
• NAKAI, T.;MIKAMI, K.;TAYA, S.;FUJITA, Y., J. AMER. CHEM. SOC., 1981, 103, N 21, 6492-6494
  作者：NAKAI, T.、MIKAMI, K.、TAYA, S.、FUJITA, Y.

  DOI：——

  日期：——