(4-methylhexa-1,5-dien-3-yl)benzene | 68060-18-4

• 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: (4-methylhexa-1,5-dien-3-yl)benzene
• 英文别名: 3-methyl-4-phenyl-hexa-1,5-diene；3-Methyl-4-phenyl-hexa-1,5-dien；4-Methylhexa-1,5-dien-3-ylbenzene
• CAS: 68060-18-4；77145-78-9；77145-84-7
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: ABIBLUJJZTYFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：

  (4-methylhexa-1,5-dien-3-yl)benzene 生成 α-methyl-β-phenylsuccinic acid
  参考文献：
  名称：

  Levy; Cope, Journal of the American Chemical Society, 1944, vol. 66, p. 1687

  摘要：

  DOI：
• 作为产物：
  描述：

  顺式-2-丁烯-1-硼酸频那醇酯 、 肉桂基氯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 (S)-(6,6′-二甲氧基联苯-2,2′-二基)双(二-2-呋喃基膦) 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以90%的产率得到(4-methylhexa-1,5-dien-3-yl)benzene
  参考文献：
  名称：

  Construction of 1,5-Enynes by Stereospecific Pd-Catalyzed Allyl–Propargyl Cross-Couplings

  摘要：

  The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

  DOI：

  10.1021/ja302329f

文献信息

• Diastereocontrol in Asymmetric Allyl–Allyl Cross-Coupling: Stereocontrolled Reaction of Prochiral Allylboronates with Prochiral Allyl Chlorides
  作者：Laura A. Brozek、Michael J. Ardolino、James P. Morken

  DOI：10.1021/ja2075967

  日期：2011.10.26

  Palladium-catalyzed allyl-ally cross-coupling was investigated with substituted prochiral allylic boronates. These reactions deliver products bearing adjacent stereocenters, and the issue of diastereocontrol is therefore paramount. Under appropriately modified conditions, this allyl allyl coupling strategy was found to apply to a range of substrates, generally occurring with high enantioselectivity (92:8 to >99:1 er) and good diastereoselection (4:1 to 14:1 dr).
• Allylic Rearrangements. XXXIII. The Reaction of Sodium Allylbenzene with Allylic Halides and Methyl Bromide
  作者：William G. Young、[not available] Kosmin、R. Y. Mixer、Tod W. Campbell

  DOI：10.1021/ja01123a009

  日期：1952.2
• Allylic Rearrangements. XXXV. The Reactions of the Sodium Derivative of Allylbenzene in n-Pentane with Methanol, Alkyl and Allylic Halides^1a
  作者：R. Y. Mixer、William G. Young

  DOI：10.1021/ja01595a032

  日期：1956.7
• Reaction of allylic boron and aluminum "ate" complexes with organic halides and carbonyl compounds. Trialkylboranes as regio-, stereo-, and chemoselective control elements
  作者：Yoshinori Yamamoto、Hidetaka Yatagai、Kazuhiro Maruyama

  DOI：10.1021/ja00398a016

  日期：1981.4
• 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.