1-(1-butyl-1,2-propadienyl)-2-methylbenzene | 1008519-29-6

• 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: 1-(1-butyl-1,2-propadienyl)-2-methylbenzene
• CAS: 1008519-29-6
• 化学式: C₁₄H₁₈
• 分子量: 186.297
• InChiKey: MCWBAEYMPNWDNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-(1-butyl-1,2-propadienyl)-2-methylbenzene 在 水 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以50%的产率得到2-fluoro-3-(o-methylphenyl)-1-hepten-3-ol
  参考文献：
  名称：

  An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor

  摘要：

  The internal C-C double bond in 3-aryl-1,2-allenes was highly regioselectively fluorohydroxylated to afford 2-fluoroalken-3-ols in 37-88% yields by using Selectfluor as the electrophilic reagent. The regioselectivity may be determined by the electronic effect, while the reactivity may be controlled by the stabilization effect of the aryl group in the allylic cationic intermediates.

  DOI：

  10.1021/ol702863n
• 作为产物：
  描述：

  2-Methyl-nonin-(4)-ol-(2) 、 2-溴甲苯 在 tris-(dibenzylideneacetone)dipalladium(0) 氢氧化钾 、 N,N-二甲基乙酰胺 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 4.0h， 以65%的产率得到1-(1-butyl-1,2-propadienyl)-2-methylbenzene
  参考文献：
  名称：

  Synthesis of Arylallenes by Palladium-Catalyzed Retro-Propargylation of Homopropargyl Alcohols

  摘要：

  Treatment of tertiary homopropargyl alcohol with aryl halide under palladium catalysis provided arylallenes regioselectively. The reaction includes retropropargylation, which proceeds in a concerted fashion via a cyclic transition state and transfers the stereochemistry of homopropargyl alcohols through C-C bond cleavage. The present method enables the use of homopropargyl alcohols as allenylmetal equivalents.

  DOI：

  10.1021/ja800986m

文献信息

• Copper-Catalyzed Intermolecular Trifluoromethylazidation and Trifluoromethylthiocyanation of Allenes: Efficient Access to CF₃-Containing Allyl Azides and Thiocyanates
  作者：Na Zhu、Fei Wang、Pinhong Chen、Jinxing Ye、Guosheng Liu

  DOI：10.1021/acs.orglett.5b01677

  日期：2015.7.17

  A mild and efficient method for copper-catalyzed trifluoromethylazidation and trifluoromethylthiocyanation of allenes was explored. A series of CF3-containing allyl azides and thiocyanates were obtained with high yields and good stereoselectivities, which can be used for further transformation to some valuable compounds.

  探索了一种温和有效的方法，用于铜的丙二烯三氟甲基叠氮化和三氟甲基硫氰化。以高收率和良好的立体选择性获得了一系列含CF 3的烯丙基叠氮化物和硫氰酸盐，可用于进一步转化为某些有价值的化合物。
• Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds
  作者：Monika M. Lindner、Udo Beckmann、Eva Eichberger、Guido J. Reiß、Wolfgang Kläui

  DOI：10.1002/ejic.200901179

  日期：2010.6

  been elucidated by investigating the reactions of such complexes with aliphatic unsaturated compounds like olefins and alkynes. We have shown that the double or triple bond, respectively, inserts into the nickel–carbon bond followed by β-hydride elimination resulting in aryl-substituted olefins and allenes, which have been identified by means of GC/MS. The remaining nickel forms a bis(N,O-chelate ligand)nickel

  包含 N,O-螯合配体的方形平面芳烃-(三苯基膦)镍 (II) 配合物 (3) 是一氧化碳/乙烯共聚反应的催化剂。通过研究此类配合物与脂肪族不饱和化合物（如烯烃和炔烃）的反应，阐明了催化剂失活的途径。我们已经表明，双键或三键分别插入镍-碳键，然后β-氢化物消除，产生芳基取代的烯烃和丙二烯，这些已通过 GC/MS 进行鉴定。剩余的镍形成双（N,O-螯合配体）镍络合物，其晶体结构已确定。镍原子由两个配体以方形平面方式配位。
• Synthesis of Arylallenes by Palladium-Catalyzed Retro-Propargylation of Homopropargyl Alcohols
  作者：Sayuri Hayashi、Koji Hirano、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1021/ja800986m

  日期：2008.4.1

  Treatment of tertiary homopropargyl alcohol with aryl halide under palladium catalysis provided arylallenes regioselectively. The reaction includes retropropargylation, which proceeds in a concerted fashion via a cyclic transition state and transfers the stereochemistry of homopropargyl alcohols through C-C bond cleavage. The present method enables the use of homopropargyl alcohols as allenylmetal equivalents.
• An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor
  作者：Chao Zhou、Jing Li、Bo Lü、Chunling Fu、Shengming Ma

  DOI：10.1021/ol702863n

  日期：2008.2.1

  The internal C-C double bond in 3-aryl-1,2-allenes was highly regioselectively fluorohydroxylated to afford 2-fluoroalken-3-ols in 37-88% yields by using Selectfluor as the electrophilic reagent. The regioselectivity may be determined by the electronic effect, while the reactivity may be controlled by the stabilization effect of the aryl group in the allylic cationic intermediates.