1-phenyl-2-vinyl-2,3-butadien-1-ol | 1078164-28-9

• 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: 1-phenyl-2-vinyl-2,3-butadien-1-ol
• CAS: 1078164-28-9
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: QRYRRQSODXHTLH-UHFFFAOYSA-N

物化性质

• 沸点：
  302.6±22.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1-phenyl-2-vinyl-2,3-butadien-1-ol 在 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以44%的产率得到2-phenyl-3-vinyl-2,5-dihydrofuran
  参考文献：
  名称：

  Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-Endo Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans

  摘要：

  Ethyl alpha-(1-hydroxy-1-alkyl)methylallenoates and alpha-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the alpha-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbony1-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.

  DOI：

  10.1021/jo2018125
• 作为产物：
  描述：

  1-溴戊-4-烯-2-炔 、 苯甲醛 在 indium 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到1-phenyl-2-vinyl-2,3-butadien-1-ol
  参考文献：
  名称：

  Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide

  摘要：

  在 $CH_2Cl_2$ 中，具有乙氧羰基和乙烯基的烯醇与三卤化铟在室温下发生反应，从而开发出一种高效的 Z 选择性 3-乙氧羰基-2-卤-1,3-二烯和 3-乙烯基-2-卤-1,3-二烯的合成方法。

  DOI：

  10.5012/bkcs.2010.31.03.645

文献信息

• Selective Indium-Mediated 1,2,4-Pentatrien-3-ylation of Carbonyl Compounds for the Efficient Synthesis of Vinyl Allenols
  作者：Jisu Park、Sung Hong Kim、Phil Ho Lee

  DOI：10.1021/ol802073q

  日期：2008.11.6

  highly selective synthetic method of functionalized vinyl allenols was developed from the reactions of various carbonyl compounds with organoindium reagent in situ generated from indium and 1-bromopent-4-en-2-yne derivatives. Treatment of vinyl allenols with gold catalyst, dienophile, or indium trihalide produced the functionalized dihydrofuran, cyclohexene, or 2-halo-1,3-diene derivatives in good to

  通过各种羰基化合物与由铟和1-溴戊-4-en-2-炔衍生物生成的有机铟试剂的反应，开发了一种高度选择性的官能化乙烯基烯丙醇的合成方法。用金催化剂，亲二烯体或三卤化铟处理乙烯基烯丙醇可以很好的产率获得官能化的二氢呋喃，环己烯或2-卤代-1,3-二烯衍生物。
• An Effective Diels-Alder Reaction of Vinyl Allenols with Dienophiles
  作者：Subin Choi、Hoon Hwang、Phil Ho Lee

  DOI：10.1002/ejoc.201001148

  日期：2011.3

  Vinyl allenols obtained from reaction of aldehydes with vinyl propargyl bromide and indium underwent Diels-Alder reactions with a variety of symmetric and unsymmetric dienophiles in dichloromethane or toluene regioselectively, producing cyclohexenylmethyl alcohols possessing an exo methylene moiety in good to excellent yield.

  由醛与乙烯基炔丙基溴和铟反应获得的乙烯基烯丙醇在二氯甲烷或甲苯中与各种对称和非对称亲二烯体发生区域选择性的 Diels-Alder 反应，产生具有外亚甲基部分的环己烯基甲醇，收率良好至极好。
• Efficient Synthetic Method of Z-Selective 2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide
  作者：Da-Han Eom、Sung-Hong Kim、Phil-Ho Lee

  DOI：10.5012/bkcs.2010.31.03.645

  日期：2010.3.20

  An efficient synthetic method of Z-selective 3-ethoxycarbonyl-2-halo-1,3-dienes and 3-vinyl-2-halo-1,3-dienes was developed from the reaction of allenols having ethoxycarbonyl and vinyl group with indium trihalides at room temperature in $CH_2Cl_2$.

  在 $CH_2Cl_2$ 中，具有乙氧羰基和乙烯基的烯醇与三卤化铟在室温下发生反应，从而开发出一种高效的 Z 选择性 3-乙氧羰基-2-卤-1,3-二烯和 3-乙烯基-2-卤-1,3-二烯的合成方法。
• Copper-Catalyzed Intramolecular Hydroalkoxylation of α-(1-Hydroxy-1-alkyl- and -aryl)methylallenoates by a 5-<i>Endo</i> Mode for Preparation of 2-Alkyl- and 2-Aryl-2,5-dihydrofurans
  作者：Sanghyuck Kim、Phil Ho Lee

  DOI：10.1021/jo2018125

  日期：2012.1.6

  Ethyl alpha-(1-hydroxy-1-alkyl)methylallenoates and alpha-(1-hydroxy-1-aryl)methylallenoates containing not only electron-donating groups but also an electron-withdrawing group on the aryl group at the alpha-position have been shown to undergo an efficient and selective copper-catalyzed intramolecular hydroalkoxylation to give functionalized 3-ethoxycarbony1-2-alkyl- and -aryl-2,5-dihydrofurans in good to excellent yields through a 5-endo mode.