1-bromo-2-(2-methoxyphenyl)penta-3,4-dien-2-ol | 1580443-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-bromo-2-(2-methoxyphenyl)penta-3,4-dien-2-ol
• CAS: 1580443-94-2
• 化学式: C₁₂H₁₃BrO₂
• 分子量: 269.138
• InChiKey: INBSBQYVJITOCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(2-methoxyphenyl)penta-3,4-dien-2-ol 在 ferric(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到(Z)-1-(1,4-dibromopenta-2,4-dien-2-yl)-2-methoxybenzene
  参考文献：
  名称：

  Synthesis of Hexahydro-1H-isoindole Derivatives from Arylacyl Bromides via Homoallenic Bromohydrins

  摘要：

  A procedure has been developed for the concise synthesis of hexahydro-H-1-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated S(N)2'-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular DielsAlder reaction of the formed ene-diene to generate the target hexahydro-H-1-isoindole.

  DOI：

  10.1021/acs.joc.5b00072
• 作为产物：
  描述：

  邻甲氧基-2-溴苯乙酮 、 3-溴丙炔 在 indium 作用下， 以66%的产率得到1-bromo-2-(2-methoxyphenyl)penta-3,4-dien-2-ol
  参考文献：
  名称：

  通过烯丙基溴醇的脱水反应 立体选择性地制备共轭（Z）-1,3-烯炔，并在与β-酮酸酯的碱介导的串联烯丙基化烯碳环化反应中使用烯炔†

  摘要：

  已经开发了一种通过Sc（OTf）3催化的烯丙基溴代醇的简明，立体选择性合成（Z）-5-溴-4-芳基-戊-3-烯-1-炔的合成方法。（Z）-1,3-Enynes进行顺序的一锅法过程时，将其转化为亚甲基环戊烯，该过程涉及与乙酰乙酸乙酯的碱介导的烯丙基化反应，然后进行烯碳环化反应。当用酸处理亚甲基环戊烯以形成高度取代的环戊二烯时，会发生涉及1,5-酰基迁移的前所未有的重排反应。

  DOI：

  10.1039/c6ob02178f

文献信息

• γ-Halo-enones: A Method for their Synthesis from Arylacyl Halides and Their Application to the Preparation of Five-Membered Ring Heterocycles
  作者：Mei-Huey Lin、Yen-Chih Huang、Chung-Kai Kuo、Chang-Hsien Tsai、Yi-Syuan Li、Ting-Chia Hu、Tsung-Hsun Chuang

  DOI：10.1021/jo5001274

  日期：2014.3.21

  A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered

  已开发出一种简单的方法来合成γ-卤代烯酮。该方法采用的序列涉及初始的铟介导的苯甲酰卤与炔丙基溴的烯丙基化反应。该过程之后是形成的高烯丙基卤代醇的酸促进的重排反应。可以将新方法结合到有效合成各种五元杂环化合物的途径中。
• Stereoselective preparation of conjugated (Z)-1,3-enynes by dehydration reactions of allenic bromohydrins and the use of the enynes in base-mediated tandem allylation ene-carbocyclization reactions with β-ketoesters
  作者：Mei-Huey Lin、Yu-Chun Chen、Shih-Hao Chiu、Kung-Yu Liang、Yi-Lin Lee、Tsung-Hsun Chuang

  DOI：10.1039/c6ob02178f

  日期：——

  procedure has been developed for the concise, stereoselective synthesis of (Z)-5-bromo-4-aryl-pent-3-en-1-ynes through Sc(OTf)3 catalyzed dehydration reactions of allenic bromohydrins. (Z)-1,3-Enynes are transformed to methylenecyclopentenes when subjected to a sequential, one-pot process involving base mediated allylation reactions with ethyl acetoacetate followed by ene-carbocyclization reactions.

  已经开发了一种通过Sc（OTf）3催化的烯丙基溴代醇的简明，立体选择性合成（Z）-5-溴-4-芳基-戊-3-烯-1-炔的合成方法。（Z）-1,3-Enynes进行顺序的一锅法过程时，将其转化为亚甲基环戊烯，该过程涉及与乙酰乙酸乙酯的碱介导的烯丙基化反应，然后进行烯碳环化反应。当用酸处理亚甲基环戊烯以形成高度取代的环戊二烯时，会发生涉及1,5-酰基迁移的前所未有的重排反应。
• Synthesis of Hexahydro-1<i>H</i>-isoindole Derivatives from Arylacyl Bromides via Homoallenic Bromohydrins
  作者：Mei-Huey Lin、Yi-Syuan Li、Chung-Kai Kuo、Chung-Hao Chen、Yen-Chih Huang、Kung-Yu Liang、Yu-Chun Chen、Chang-Hsien Tsai、Tsung-Hsun Chuang

  DOI：10.1021/acs.joc.5b00072

  日期：2015.2.20

  A procedure has been developed for the concise synthesis of hexahydro-H-1-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated S(N)2'-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular DielsAlder reaction of the formed ene-diene to generate the target hexahydro-H-1-isoindole.