(E)-4-hydroxy-1-methyl-1-phenyl-2-butene-1-ol | 674368-15-1

• 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: (E)-4-hydroxy-1-methyl-1-phenyl-2-butene-1-ol
• 英文别名: (E)-4-phenylpent-2-ene-1,4-diol
• CAS: 674368-15-1
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: XZXYETXARRYLAS-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-1-methyl-1-phenyl-2-butene-1-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 1,2-双(二苯基膦)乙烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (+/-)-(1S,2R)-1,2-carbonyldioxy-1-methyl-1-phenyl-2-vinylethane
  参考文献：
  名称：

  Palladium-Catalyzed Carbon Dioxide Elimination−Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols

  摘要：

  A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.

  DOI：

  10.1021/jo0353280
• 作为产物：
  描述：

  4-phenyl-2-pentyne-1,4-diol 在 lithium aluminium tetrahydride 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以55%的产率得到(E)-4-hydroxy-1-methyl-1-phenyl-2-butene-1-ol
  参考文献：
  名称：

  Palladium-Catalyzed Carbon Dioxide Elimination−Fixation Reaction of 4-Methoxycarbonyloxy-2-buten-1-ols

  摘要：

  A new type of palladium-catalyzed CO2 recycling reaction using allylic carbonates is described. Reaction of trans-4-methoxycarbonyloxy-2-buten-1-ols in the presence of a palladium catalyst produces cyclic carbonates having a vinyl group via a CO2 elimination-fixation process. A variety of allylic carbonates participate in the reaction giving cyclic carbonates with high efficiencies. Stereoselective construction of trans-cyclic carbonates is achieved by using nonsymmetric substrates. An enantiospecific reaction proceeds to give chiral cyclic carbonate when a chiral methyl-substituted substrate is subjected to the reaction conditions.

  DOI：

  10.1021/jo0353280

文献信息

• Atom-Transfer Radical Addition of Alcohols to Aliphatic Alkynes
  作者：Yingxia Xiao、Zhong-Quan Liu

  DOI：10.1021/acs.joc.9b00804

  日期：2019.8.2

  An intermolecular hydrogen bond-promoted atom-transfer radical addition of simple alcohols to aliphatic alkynes is demonstrated here. Through this strategy, a variety of allyl alcohols can be synthesized in high selectivity and yields. Furthermore, this work reveals the relationship between selectivity and the substrate.

  在此证明了单醇的分子间氢键促进的原子转移自由基加成到脂肪族炔烃上。通过这种策略，可以高选择性和高产率合成多种烯丙醇。此外，这项工作揭示了选择性与底物之间的关系。
• Epoxidation and cyclopropanation of 2-silyl-3-alkenols. A study of 1,2-asymmetric induction
  作者：Yannick Landais、Liliana Parra-Rapado

  DOI：10.1016/0040-4039(95)02386-0

  日期：1996.2

  Epoxidation and cyclopropanation of 2-silyl-3-alkenols have been shown to occur with high 1,2-stereocontrol through substrate directable reactions. Both syn and anti epoxides are thus available from E and Z-allylsilanes. This contrasts with the results usually observed for allylsilanes lacking a coordinating group.

  已经显示，通过底物可指导的反应，在高1,2-立体控制下，发生了2-甲硅烷基-3-链烯醇的环氧化和环丙烷化反应。无论SYN和抗氧化物，因此可从Ë和ž -allylsilanes。这与缺乏配位基团的烯丙基硅烷通常观察到的结果相反。
• REICH, H. J.;WOLLOWITZ, S., J. AMER. CHEM. SOC., 1982, 104, N 25, 7051-7059
  作者：REICH, H. J.、WOLLOWITZ, S.

  DOI：——

  日期：——