(5-methylhexa-1,5-dien-3-yl)benzene | 73222-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5-methylhexa-1,5-dien-3-yl)benzene
• 英文别名: 2-methyl-4-phenyl-1,5-diene；5-Methylhexa-1,5-dien-3-ylbenzene
• CAS: 73222-66-9
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: VPYVTPNAYHLZDE-UHFFFAOYSA-N

物化性质

• 沸点：
  229.0±20.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (5-methylhexa-1,5-dien-3-yl)benzene 在 四氟硼酸-二乙醚络合物 、 potassium fluoride 、 <(Cp^TMS)2YMe>2 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 环己烷 为溶剂， 反应 25.0h， 生成 ((1R,3S)-1-Methyl-3-phenyl-cyclopentyl)-methanol
  参考文献：
  名称：

  Catalytic Cyclization/Silylation of Dienes Containing 1,1-Disubstituted Olefins Using Organolanthanide and Group 3 Organometallic Complexes

  摘要：

  The catalytic cyclization/silylation reaction of hindered dienes has been investigated using the relatively unhindered complexes Me2Si(C5H3SiMe3)(2)YCH(TMS)(2) and [Cp(2)(TMS)LnMe](2) (Ln = Y, Lu). A nide variety of dienes and trienes bearing a number of functional groups were cyclized, affording silanes containing quaternary centers in a diastereoselective fashion and in good yield. The products can be oxidized using one of several different protocols, yielding alcohols for further functionalization.

  DOI：

  10.1021/jo972359k
• 作为产物：
  描述：

  4,4,5,5-四甲基-2-(2-甲基烯丙基)-1,3,2-二噁硼烷 、 cinnamyl tert-butyl carbonate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,2-双(二苯基膦基)苯 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (5-methylhexa-1,5-dien-3-yl)benzene
  参考文献：
  名称：

  Pd-Catalyzed Enantioselective Allyl−Allyl Cross-Coupling

  摘要：

  The Pd-catalyzed cross-coupling of allylic carbonates and allyIB(pin) is described. The regioselectivity of this reaction is sensitive to the bite angle of the ligand, with small-bite-angle ligands favoring the branched substitution product. This mode of regioselection is consistent with a reaction that operates by a 3,3' reductive elimination reaction. In the presence of appropriate chiral ligands, this reaction is rendered enantioselective and applies to both aromatic and aliphatic allylic carbonates.

  DOI：

  10.1021/ja105161f

文献信息

• Tandem Cyclization/Hydroarylation of α,ω-Dienes Triggered by Scandium-Catalyzed C–H Activation
  作者：Bin Tang、Xiaoyan Hu、Chunli Liu、Tao Jiang、Fakhre Alam、Yanhui Chen

  DOI：10.1021/acscatal.8b04713

  日期：2019.1.4

  regio- and diastereoselective cyclization/hydroarylation reaction of 1,5- and 1,6-dienes with aromatic ethers and tertiary anilines was established by a cationic 2-picoline-tethered-half-sandwich scandium alkyl catalyst, which constitutes a process for producing a diverse array of cis-1,3-disubstituted arylated and trans-1,2-disubstituted benzylated methylcyclopentane derivatives in one step with 100% atom-efficiency

  1，5-和1，6-二烯与芳族醚和叔苯胺的高度区域和非对映选择性环化/氢芳基化反应是通过阳离子2-甲基吡啶系留的半三明治s烷基烷基催化剂建立的，一步以100％的原子效率生产多种顺式-1,3-二取代的芳基化和反式-1,2-二取代的苄基化甲基环戊烷衍生物。此外，还提出了涉及involving催化的芳族邻-C-H活化和烯烃插入级联反应的机理。
• Iridium-Catalyzed Enantioselective Allyl–Alkene Coupling
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1021/ja412962w

  日期：2014.2.26

  The direct Ir-catalyzed cross-coupling between branched, racemic allylic alcohols and simple olefins is described. This transformation is catalyzed by an Ir-(P,olefin) complex and proceeds with high site selectivity and excellent enantioselectivity. The method allows rapid access to various 1,5-dienes or trienes and was used in the catalytic asymmetric synthesis of the gamma-secretase modulator JNJ-40418677.
• Catalyzed sigmatropic rearrangements. 5. Palladium(II) chloride catalyzed Cope rearrangements of acyclic 1,5-dienes
  作者：Larry E. Overman、Frederick M. Knoll

  DOI：10.1021/ja00522a082

  日期：1980.1
• Oxovanadium-induced oxidative desilylation of allylic and benzylic silanes
  作者：Takashi Fujii、Toshikazu Hirao、Yoshiki Ohshiro

  DOI：10.1016/s0040-4039(00)73892-5

  日期：1993.8

  Cinnamyltrimethylsilane underwent desilylation via one-electron oxidation with VO(OEt)Cl2, which was applied to the cross-coupling with the less oxidizable allylic silanes to give the corresponding 1,5-hexadienes. Chlorination or aromatization based on desilylation was observed on treatment of benzyltrimethylsilane or 3-ethoxycarbonyl-2-methyl-5-trimethylsilyl-5-phenyl-4,5-dihydrofuran with VO(OEt)Cl2-Me3SiOTf, respectively.