(4E)-1,4-octadien-3-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4E)-1,4-octadien-3-ol
• 英文别名: (E)-octa-1,4-dien-3-ol；(4E)-octa-1,4-dien-3-ol
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: JKMHYJRORPXHGQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (4E)-1,4-octadien-3-ol 在 Grubbs catalyst first generation 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 58.25h， 生成 (+)-lethaloxin
  参考文献：
  名称：

  Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

  摘要：

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.

  DOI：

  10.1021/jo202199g
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 二甲基亚砜 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (4E)-1,4-octadien-3-ol
  参考文献：
  名称：

  Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

  摘要：

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.

  DOI：

  10.1021/jo202199g

文献信息

• Ruthenium-Catalyzed Redox Isomerizations inside Living Cells
  作者：Cristian Vidal、María Tomás-Gamasa、Alejandro Gutiérrez-González、José L. Mascareñas

  DOI：10.1021/jacs.9b00837

  日期：2019.4.3

  Tailored ruthenium(IV) complexes can catalyze the isomerization of allylic alcohols into saturated carbonyl derivatives under physiologically relevant conditions, and even inside living mammalian cells. The reaction, which involves ruthenium-hydride intermediates, is bioorthogonal and biocompatible, and can be used for the “in cellulo” generation of fluorescent and bioactive probes. Overall, our research

  定制的钌(IV)络合物可以在生理相关条件下甚至在活的哺乳动物细胞内催化烯丙醇异构化为饱和羰基衍生物。该反应涉及氢化钌中间体，具有生物正交性和生物相容性，可用于“细胞内”生成荧光和生物活性探针。总的来说，我们的研究揭示了一种新型的基于金属的细胞干预工具，并进一步证明了有机金属机制与细胞复杂环境的兼容性。
• Ir-Catalyzed Regiocontrolled Allylic Amination of Di-/Trienyl Allylic Alcohols with Secondary Amines
  作者：Shengbiao Tang、Ziyong Li、Ying Shao、Jiangtao Sun

  DOI：10.1021/acs.orglett.9b02435

  日期：2019.9.20

  An unprecedented regio-controllable allylic amination of unactivated dienyl and trienyl allylic alcohols has been developed, providing an efficient approach toward the site-selective formation of C1-, C3-, and C5-/C7-amination products from the sole substrates. Key to this protocol is the use of secondary amines as the amination reagents, as well as the presence of an iridium catalyst and scandium

  已经开发了空前的未活化的二烯基和三烯丙基烯丙基醇的区域可控的烯丙基胺化，为从单一底物选择性地形成C1-，C3-和C5- / C7-胺化产物提供了一种有效的方法。该方案的关键是使用仲胺作为胺化试剂，以及存在铱催化剂和三氟甲磺酸scan。
• Synthesis of New 3-(-2-Alkenyl)-2-hydroxy-5-methoxy-<i>p</i>-benzoquinones via Claisen Rearrangement of Original 5-Methoxy-4-(2-propenyloxy)-<i>o</i>-benzoquinones
  作者：Olivia Reinaud、Patrice Capdevielle、Michel Maumy

  DOI：10.1055/s-1988-27547

  日期：——

  The Claisen rearrangement is extended to compounds containing the benzoquinone moiety, obtained by regioselective nucleophilic substitution on 4-(p-methoxyphenoxy)-5-methoxy-o-benzoquinone (1). In the most general case, 5-methoxy-4-(2-propenyloxy)-o-benzoquinones 3 rearrange quantitatively into (E)-3-(2-alkenyl-2-hydroxy-5-methoxy-p-benzoquinones 4. Furfuryl or (2-thienyl)methyl ethers isomerize to 3-(2-methyl-3-furyl)- and 3-(2-methyl-3-thienyl)-2-hydroxy-5-methoxy-p-benzoquinones. This new synthetic method provides an efficient route to new hydroxybenzoquinones closely related to natural compounds. Thus, dihydroardisiaquinone A is synthesized in 5 steps from p-methoxyphenol.

  克莱森重排扩展到含有苯醌部分的化合物，该化合物通过 4-(对甲氧基苯氧基)-5-甲氧基-邻苯醌 (1) 上的区域选择性亲核取代获得。在最常见的情况下，5-甲氧基-4-(2-丙烯氧基)-邻苯醌 3 定量重排成 (E)-3-(2-烯基-2-羟基-5-甲氧基-对苯醌 4)。或(2-噻吩基)甲基醚异构化为3-(2-甲基-3-呋喃基)-和3-(2-甲基-3-噻吩基)-2-羟基-5-甲氧基-对苯醌。该方法为与天然化合物密切相关的新羟基苯醌提供了一条有效的途径，因此，二氢紫心醌A是由对甲氧基苯酚通过5步合成的。
• Catalytic Palladium-Mediated Bisdiene Carbocyclizations:  Bisdiene to Enediene Cycloisomerizations
  作者：James M. Takacs、Francis Clement、Jingyang Zhu、Sithamalli V. Chandramouli、Xiaoping Gong

  DOI：10.1021/ja962748g

  日期：1997.6.1

  The palladium-catalyzed cycloisomerization of acyclic bisdienes to cyclized enedienes defines a novel strategy for the stereoselective cyclization of certain unsymmetric bisdiene substrates to form functionalized five- and six-membered rings. The full details of our investigation into this novel cycloisomerization, including our observations on substrate requirements, stereoselectivity, the influence

  钯催化的无环双二烯环化异构化为环化烯二烯定义了一种新策略，用于某些不对称双二烯底物的立体选择性环化以形成功能化的五元和六元环。讨论了我们对这种新型环异构化的研究的全部细节，包括我们对底物要求、立体选择性、催化剂前体的影响以及从氘标记研究中得出的一些机械见解的观察。
• Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides
  作者：Palakodety Radha Krishna、D. Venkata Ramana

  DOI：10.1021/jo202199g

  日期：2012.1.6

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.