2,5-dimethylhexa-3,4-dien-1-ol | 84672-41-3

• 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: 2,5-dimethylhexa-3,4-dien-1-ol
• CAS: 84672-41-3
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: PCDIPSKWONSQRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  2,5-dimethylhexa-3,4-dien-1-ol 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 6-iodo-2,5-dimethylhexa-2,3-diene
  参考文献：
  名称：

  均烯基

  摘要：

  通过相应的碘化物与Bu 3 SnH的反应已经产生了几个同烯丙基基团，发现除了烯丙基烃以外，还产生了少量的乙烯基环丙烷，从而确定了同烯丙基基团环化成异构的1-环丙基乙烯基基团。

  DOI：

  10.1016/s0040-4039(00)87702-3
• 作为产物：
  描述：

  2-甲基-3-丁炔-2-醇 在 丙酸 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,5-dimethylhexa-3,4-dien-1-ol
  参考文献：
  名称：

  Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2H-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides

  摘要：

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.

  DOI：

  10.1021/jo0163997

文献信息

• On the Gold-Catalyzed Intramolecular 7-<i>exo-trig</i>Hydroamination of Allenes
  作者：Daniel Pflästerer、Praphasiri Dolbundalchok、Shahid Rafique、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201300154

  日期：2013.5.3

  allene side tethers were tested as substrates for a gold‐catalyzed 7‐exo‐trig hydroamination reaction. The nucleophilicity of the aniline derivatives plays an important role for the outcome of the reaction. While electron‐deficient protecting groups at the nitrogen led to competing pathways like hydroarylation or an allene to diene isomerization, clean formation of the desired benzoxazepines was obtained

  以苯丙氨酸侧链为苯胺衍生物作为金催化的7 exo-trig加氢胺化反应的底物进行了测试。苯胺衍生物的亲核性对反应的结果起重要作用。尽管氮上缺乏电子的保护基团导致竞争途径（如氢芳基化或丙二烯向二烯异构化），但使用未保护的苯胺衍生物可以清晰地形成所需的苯并a氮平。
• Bi(OTf)₃-Catalyzed Cycloisomerization of Aryl-Allenes
  作者：Gilles Lemière、Bastien Cacciuttolo、Emilie Belhassen、Elisabet Duñach

  DOI：10.1021/ol3009667

  日期：2012.6.1

  Intramolecular hydroarylation of allenes was achieved under very mild conditions using bismuth(III) triflate as the catalyst. Efficient functionalization of activated and nonactivated aromatic nuclei led to C–C bond formation through a formal Ar–H activation. A tandem bis-hydroarylation of the allene moiety was also developed giving access to various interesting polycyclic structures.

  使用三氟甲磺酸铋（III）作为催化剂，在非常温和的条件下实现了烯丙基的分子内加氢芳基化。活化和未活化的芳香核的有效功能化通过正式的Ar–H活化导致C–C键形成。还开发了Allene部分的串联双氢芳基化，从而可以使用各种有趣的多环结构。
• CRANDALL, J. K.;TINDELL, G. L.;MANMADE, A., TETRAHEDRON LETT., 1982, 23, N 37, 3769-3772
  作者：CRANDALL, J. K.、TINDELL, G. L.、MANMADE, A.

  DOI：——

  日期：——
• Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2<i>H</i>-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides
  作者：Shengming Ma、Wenzhong Gao

  DOI：10.1021/jo0163997

  日期：2002.8.1

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.
• Homoallenyl radicals
  作者：J.K Crandall、G.L Tindell、A Manmade

  DOI：10.1016/s0040-4039(00)87702-3

  日期：1982.1

  Several homoallenyl radicals have been generated by the reaction of the corresponding iodides with Bu3SnH and found to produce small amounts of vinylcyclopropanes in addition to allene hydrocarbons establishing that homoallenyl radicals cyclize to isomeric 1-cyclopropylvinyl radicals.

  通过相应的碘化物与Bu 3 SnH的反应已经产生了几个同烯丙基基团，发现除了烯丙基烃以外，还产生了少量的乙烯基环丙烷，从而确定了同烯丙基基团环化成异构的1-环丙基乙烯基基团。