3-Phenyl-4-hexen-3-ol

• 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: 3-Phenyl-4-hexen-3-ol
• 英文别名: 3-phenylhex-4-en-3-ol；(E)-3-phenylhex-4-en-3-ol
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: XPGSEBBEYLJAHG-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-Phenyl-4-hexen-3-ol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 苯 为溶剂， 反应 5.0h， 以76%的产率得到syn-/anti-2,3-Epoxy-4-phenylhexan-4-ol
  参考文献：
  名称：

  Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms

  摘要：

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

  DOI：

  10.1021/jo00074a019
• 作为产物：
  描述：

  4-己烯-3-酮 、 苯基锂 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 以31%的产率得到3-Phenyl-4-hexen-3-ol
  参考文献：
  名称：

  Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms

  摘要：

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

  DOI：

  10.1021/jo00074a019

文献信息

• Microwave-enhanced radical reactions at ambient temperature : Part 3: Highly selective radical synthesis of 3-cyclohexyl-1-phenyl-1-butanone in a microwave double cylindrical cooled reactor
  作者：Satoshi Horikoshi、Junichi Tsuzuki、Masatsugu Kajitani、Masahiko Abe、Nick Serpone

  DOI：10.1039/b810142f

  日期：——

  system (MW/Cool protocol) for a reaction temperature of 20–24 °C exceeded the yields from the reaction occurring at room temperature (24 °C; no microwaves; 40% and 72%) for the same reaction times and temperature. The competitive radical reaction to produce CPB and a small amount of by-products generated from the thermally-induced synthesis by the non-selective radical reaction was restricted solely to the

  微波强化合成3-环己基-1-苯基-1-丁酮（CPB） 巴豆酮 和 碘代环己烷在t -BuOOH和三乙基硼烷使用不少于四种不同的合成方案，在室温和回流条件下，对本体溶液进行了分析。反应温度为20–24°C的微波介电加热和冷却系统（MW / Cool规程）耦合60和120分钟后，CPB的化学收率（分别为93％和95％）超过了发生的反应的收率在室温（24°C；无微波； 40％和72％）下进行相同的反应时间和温度。产生CPB的竞争性自由基反应以及通过非选择性自由基反应由热诱导合成产生的少量副产物仅限于在环境温度下发生的过程（RT方案），在微波介电下加热至回流（MW规程），并用油浴加热至回流（油浴规程）。相比之下，通过MW / Cool方法，对于反应进行没有产生或检测出副产物。在相同温度条件下比较产品收率，在标题化合物的合成中必须涉及某些特定的微波效应。
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.